Machiavelli and the Profession of Arms: Cesare Borgia as a Mercenary Prince

Abstract

The figure of Cesare Borgia occupies a complex and revealing place in the political thought of Niccolò Machiavelli. This article argues that the historical Cesare complicates Machiavelli’s more schematic presentation of military autonomy in The Prince. Whereas Chapter VII foregrounds Cesare’s dependence on Alexander VI, fortuna, French assistance, and contingent political circumstances, Chapter XIII presents a compressed movement from French auxiliaries and mercenary captains to “own” arms. By reconstructing the composition, financing, and command structures of Cesare’s forces, the article shows that his attempts to reduce dependence remained incomplete. His military power remained structurally dependent on papal finance, French backing, mercenary captains, intermediaries, and temporary forms of local recruitment. Cesare therefore did not consolidate the kind of stable territorial military apparatus that Machiavelli elsewhere identified as essential to durable rule. His rapid collapse after Alexander VI’s death reflects the fragility of a principality built on external, negotiated, and revocable support. The article thus reframes Cesare not as a historical exemplar of achieved Machiavellian military self-sufficiency, but as a figure whose career exposes the tension between Machiavelli’s theoretical use of armi proprie and the composite realities of warfare in Renaissance Italy.

1. Introduction

In the closing chapter of Book I of the Florentine Histories, Machiavelli presents Italy’s weakness as a structural failure shared by rulers and soldiers alike. The core problem, he argues, was that the “principal powers were without arms of their own,” leaving “Italian arms […] in the hands of lesser princes [minori principi] or men without territories [uomini senza stato]” (Machiavelli 1888, p. 49). The uomini senza stato are central to Machiavelli’s analysis: professional soldiers, “raised from infancy in [a culture of] arms,” who, “knowing no other profession [arte], sought by means of arms to gain wealth and power.” Lacking territorial ties, they were militarily effective yet politically dangerous, serving states while pursuing their own advancement. Machiavelli illustrates this dynamic through figures such as Francesco Bussone, who changed sides between Venice and the Visconti before ultimately being executed, and Francesco Sforza, who transformed military service into sovereign rule in Milan. Even Sforza’s success underscores the danger: mercenary service could become a path to sovereignty, thereby undermining the very states that relied upon it. Nevertheless, as Machiavelli underlines in Chapter VII of The Prince, where Cesare Borgia [Valentino] first appears prominently, Sforza remains the only genuine example of a ruler who successfully laid the foundations of a principality in advance. In Machiavelli’s judgement, once he became duke of Milan, Sforza had “acquired with a thousand difficulties” what he then “maintained with very little effort” (Machiavelli 1961, p. 23).

In Chapter XIII of The Prince, Machiavelli extends his critique, describing auxiliaries as “the other type of useless arms” (Machiavelli 1961, p. 48). His discussion of Cesare Borgia reinforces this point: Borgia’s campaigns relied first on “French auxiliaries” and subsequently on mercenary leaders, exemplifying the dangers of depending on forces with divided loyalties. Only after recognising these risks did Cesare decide to abandon them and rely on his “own” arms [alle proprie]. Machiavelli argues that this shift improved Cesare’s reputation. While he depended on mercenaries and auxiliaries, his position was insecure; once he relied on his “own” forces, he was considered “highly esteemed” [stimato assai] (Machiavelli 1961, p. 49). Yet this claim presents a problem. Machiavelli offers no concrete explanation of when or how Cesare acquired these “own” arms. Nor does the historical record suggest that Cesare ever freed himself from reliance on French support and mercenary forces. The silence of The Prince on this point suggests that Machiavelli’s account is less descriptive than prescriptive. It does not correspond to the more complex picture that emerges from his contemporary diplomatic writings, especially the legations, where Cesare’s political and military position appears far more contingent and unstable.

Cesare’s case thus illuminates a broader distinction that runs throughout The Prince: the distinction between acquiring power and securing it. His career shows that rulers who depend on external forces, however capable they may appear, remain exposed to powers beyond their control. A revealing indication of the issue appears in October 1502, when Machiavelli noted that Cesare had ordered the assembly of men “from his territories” [che sono degli Stati suoi] (Machiavelli 1875b, vol. 2, p. 76). That episode, discussed below, points directly to the interpretive difficulty at issue here. As Miguel Ángel Granada has argued, Machiavelli’s reading of such developments was shaped by Florence’s own military and political needs, especially after the failures of condottiere warfare in the struggle against Pisa (Granada 2000, p. 170). It is striking that, in a letter to Francesco Vettori in 1515, Machiavelli could still refer to “duke Valentino, whose actions I would always imitate if I were a new prince” (Machiavelli 1971b, p. 1191). Yet by the time L’Arte della guerra was completed some five years later, when Machiavelli’s conception of the citizen militia had fully matured, Cesare occupied only a marginal place.1

This tension defines the central argument of the article: Cesare Borgia should be understood not as a ruler who secured military autonomy, but as a prince whose authority remained dependent on papal finance, French military support, and mercenary captains and intermediaries. By “mercenary prince,” I do not mean that Cesare simply acted as a condottiere, nor do I deny that he sought to reduce that dependence. Rather, I use the term to describe a ruler whose military capacity, even after acquiring princely office, continued to rest on external patronage, hired troops, and negotiated service relationships rather than on a stable territorial military apparatus of his own. This formulation also clarifies the article’s historiographical target. The historians and political theorists cited in this article recognise, in different ways, the contingent, negotiated, and externally supported character of Cesare’s power. The question is therefore not whether Cesare depended upon others, a point few would deny, but how far his attempts to reduce that dependence can be understood as a meaningful movement towards armi proprie. Furthermore, in The Prince, a firm foundation in armi proprie is not treated as a final achievement, but as the necessary beginning of political consolidation (Hörnqvist 2010, p. 118).

These factors shed further light on the relationship between Chapters VII and XIII of The Prince. In Chapter VII, Machiavelli says that Cesare had “armed himself in his own way [armato a suo modo]” and destroyed the unfaithful forces on which he had previously relied. Yet the nature of these “own” arms remains unclear at this point. The phrase could be read as an allusion to Cesare’s recruitment system in the Romagna, but Machiavelli does not yet define it as a stable militia or as a fully developed form of armi proprie. It is only in Chapter XIII that he returns to Cesare’s example and makes the military lesson explicit: the duke’s reform lay in replacing unreliable auxiliary and mercenary forces with arms that Machiavelli presents as “his own” (Chabod 1964, p. 146). As Section 5 will demonstrate, John Larner’s work on the Romagnol militia (Larner 1966) is especially important in this respect, since it provides the strongest historical basis for assessing, in concrete terms, the relationship between Cesare’s military capacity, armi proprie, and the limits of these presumed innovations in institutional terms.

Although Machiavelli praises Cesare’s efforts to overcome his dependence on his father, the French, and mercenary arms, he never loses sight of the essential fact that he ultimately failed to preserve his state. Machiavelli insists that a prince of great virtù may try to build foundations after acquiring power through fortune, but such a process is necessarily difficult and dangerous. Cesare did lay “strong foundations” for future power, and Machiavelli even claims that he could offer no better example to a new prince (Machiavelli 1961, p. 23). Yet these “foundations” mentioned in Chapter VII and more clearly developed in Chapter XIII did not save him. The central tension, therefore, lies in explaining how Cesare could serve as an exemplary model while also demonstrating the dangers of trying to establish autonomy after gaining power through the “arms and fortune of others”. Framed in these terms, the article addresses two related questions: to what extent can Cesare be understood as a “mercenary prince,” and what does this reveal about Machiavelli’s wider claim that durable political power required military autonomy? In doing so, the article analyses the use of Cesare as evidence for Machiavellian armi proprie by arguing that the historical Cesare remained dependent on forms of support that were external, negotiated, and ultimately revocable. The argument proceeds in three steps: Section 2 reconstructs the political, legal, and fiscal foundations of Cesare’s fortuna within Machiavelli’s writings and the framework of papal power. Section 3 and Section 4 examine the external and negotiated character of his military capacity, especially his dependence on French support and condottieri. Section 5 turns to the concrete terms of armi proprie by analysing recruitment from his own territories and argues that these measures remained too limited, temporary, and heterogeneous to constitute any kind of stable military foundation.

2. Cesare and His Fortuna

The first reference to fortuna in relation to Cesare Borgia in Machiavelli’s legations2 dates to 26 June 1502, four days after he learned that Cesare had seized Urbino without a shot being fired. Machiavelli argued that the “way” [modo] in which Cesare achieved this victory owed much to “cleverness” [prudenzia] (Machiavelli 1875b, vol. 2, p. 5). Feigning a move against Camerino, Cesare advanced 2000 men from his main army along the Via Flaminia in a rapid march, while his artillery moved unopposed into the duchy. At the same time, he summoned Romagnol troops from the east, thereby catching his opponent, Guidobaldo da Montefeltro, completely off guard (Volpe 2005). Already on 22 June, Machiavelli had attributed this success not only to Cesare’s “swiftness” [celerità], but also to his felicità—a term that may here be translated as “fortune”. Four days later, he reinforced this point by referring explicitly to the duke’s “perpetual fortune” [perpetua fortuna] (Machiavelli 1875b, vol. 2, p. 15).

What underwrote this fortuna? As Machiavelli writes in The Prince, Cesare “acquired the state [lo stato] with the fortune [fortuna] of his father, and with that, he also lost it” (Machiavelli 1961, p. 23). This formulation is significant because it places the origins of Cesare’s power not in his own virtù, but in the political opportunities created by Pope Alexander VI. The papacy provided Cesare not only with formal legitimacy but also with the diplomatic leverage, financial resources, and legal backing necessary to undertake his campaigns. Any analysis of Cesare’s political project must therefore ask whether his rule represented an innovative attempt to build a centralised proto-state, or simply a continuation of the traditional papal policy of recuperatio. The key issue is that Cesare always remained a “papal creation,” raising the question of how far his position depended on traditional papal practices of mediation and compromise. Giovanni Soranzo observed that “to secure for each of his sons […] a principality […] was, at the time, considered almost a duty for a pope” (Soranzo 1960, pp. 344–45). Furthermore, Soranzo suggested that Alexander VI may have intended—though never fully pursued—a broader plan to consolidate the entire Italian peninsula under direct ecclesiastical control, thereby preventing foreign domination. Contemporary chroniclers such as Jacopo Nardi could write that Cesare’s aim was ultimately that of “driving out the French” from the Italian peninsula and eventually aspire to “the rule [monarchia] of Italy” (Nardi 1838, vol. 1, pp. 261, 337). Furthermore, Piero Pieri’s reading of the political situation in Italy linked the Italian states’ reliance on mercenary cavalry to its lack of native infantry, a deficiency that, in his view, condemned the peninsula to failure when confronted by the French challenge. This is why Cesare’s presumed political and military “originality,” read through the lens of nineteenth-century nationalist assumptions, led scholars such as Pieri to present him as “a precursor of the modern state” (Pieri 1952, p. 601). Yet the notion of a forte Stato della Chiesa acting di contro allo straniero never materialised. Rather, as will be seen—particularly in relation to Cesare’s army—the opposite tendency ultimately prevailed.

Such an interpretation has persisted for a long time because, as Maurizio Viroli has underlined, the message of The Prince is one of “redemption”, written “to design and invoke a redeemer of Italy capable of creating, with God’s help, new and good political order, thereby attaining perennial glory” (Viroli 2014, p. 3). Hans Baron likewise identified national redemption as a central theme of Machiavelli’s work and argued that The Prince grew out of the personal and intellectual experience Machiavelli underwent during his enforced solitude at Sant’Andrea in Percussina in the second half of 1513. Alongside his renewed engagement with classical texts, Machiavelli drew on the diplomatic skills and administrative experience he had acquired in the service of the Florentine Republic in order to formulate “the rule of a new prince.” For Baron, the chief impulse behind The Prince was Machiavelli’s desire to return to political action, combined with his wounded Italian patriotism, which led him to hope for a powerful founder of a new state. Baron also stresses that this imagined founder differs significantly from the examples Machiavelli presents in the Discourses, thereby reinforcing the distinctions which are to be found between his works (Baron 1961, pp. 242, 248).

In this same vein, Quentin Skinner offered an influential reading of The Prince within the tradition of Italian humanism. Rather than treating it as a work sui generis, Skinner argued that it was both a recognisable contribution to the genre of advice books for princes and a radical critique of that tradition. Machiavelli’s innovation lay in rejecting the humanist and Christian assumption that a prince must always follow virtues such as justice, prudence, clemency, and honesty. For Machiavelli, a truly effective ruler had to adapt his conduct to fortune and demonstrate military capacity by raising and commanding loyal troops (Skinner 1978). Skinner therefore sees the “Exhortation [esortazione]” of Chapter XXVI as central to the work’s concern with virtù, redefined as the ability to maintain the state [mantenere lo stato] while establishing a government that brings honour to the ruler and benefits his subjects (Skinner 2002, p. 41).

John G. A. Pocock similarly reads The Prince as “an analytic study of innovation and its consequences,” focused on Machiavelli’s central political concern: the “problem of fortuna.” For Pocock, the work is “a typology of innovators and their relations with fortuna,” in which the “innovator” gradually replaces the “new prince,” since the former “is more comprehensive and capable of greater theoretical precision than the latter.” Yet Pocock does not treat the final exhortation as the culmination towards which the preceding chapters “are to be seen as leading up to.” Instead, he argues that Machiavelli offers not “a single rounded portrait, but a gallery of specimen types of innovators.” Thus, for Pocock, The Prince is less a specific program of national redemption than a broader analysis of political innovation and its relation to fortuna (Pocock 1975, pp. 155–80).

Cesare stands at the center of debates over such a political theory. Many readers of The Prince, struck by the apparent relish with which Machiavelli recounts his acts of violence, have concluded that Cesare was simply Machiavelli’s hero. The view that Borgia became central to Machiavelli’s political imagination begins with the claim that Machiavelli’s early encounters with the duke inspired a sense of awed admiration. According to this interpretation, Machiavelli came to identify with Borgia’s ambitions and to merge them with his own political hopes, producing what Gennaro Sasso described as a form of psychological projection, in which “the duke was really becoming Machiavelli’s hero” (Sasso 1966, p. 92). In line with this view, other scholars such as Mark Hulliung have maintained that, despite his flaws, Cesare represented Machiavelli’s idealized “man of virtù,” or even a model for Machiavelli’s own conception of statecraft (Hulliung 1983, p. 192). Others, on the other hand, particularly Garrett Mattingly, have interpreted Machiavelli’s focus on Cesare as evidence that The Prince should be read as a work of satire, arguing that the very choice of such a morally troubling figure reveals Machiavelli’s concealed critical intention (Mattingly 1958). In other words, it served to reveal the corrupt reasoning of contemporary princes, at a time when moral judgment had become so distorted that the actions of deceitful and violent ancient rulers were widely admired and imitated. The strongest evidence for reading The Prince ironically, however, according to Leo Strauss, lies in the style of the text itself. As Strauss observed, Machiavelli’s style repeatedly combines confident assertions with anxious, doubtful, or ominous undertones, followed by extended reflections on how difficult—or even impossible—it is to achieve the goals presented with such apparent certainty. Given Machiavelli’s logical precision and literary control, such tensions strongly suggest the presence of irony (Strauss 1958).

For the main argument of this article, Erica Benner’s reading of Machiavelli’s metaphorical language is especially useful. As Benner suggests, the phrase armi proprie is not merely a technical military category but one of Machiavelli’s key devices for developing the central opposition of The Prince: virtù provides firmer foundations for political success than fortuna. Although the expression has an obvious military meaning, it also carries economic, civic, legal, and philosophical implications: themes that appear prominently in Chapters X and XII–XIV (Benner 2013, p. xlvii). This wider meaning of armi proprie helps explain why Cesare’s example remains so unstable. If “own arms” means more than troops recruited from territories under one’s control, then the question is not simply whether Cesare assembled local forces, but whether those forces were institutionally, politically, and militarily his own in any durable sense.

Scholars have thus often tried to explain the puzzle of The Prince by situating Cesare within the political context of his own Italy. Baron, for example, argues that Machiavelli’s final exhortation sought to “redeem” Italy by presenting the then-ruling Medici with a “unique occasion”: their control of both Florence and the papacy gave them the chance to expel the “barbarians” and found a strong new state, modeled on the power Cesare had briefly built in north-central Italy (Baron 1991). John Humphreys Whitfield offers a similar interpretation, seeing Cesare’s career as the only historical precedent for what could be achieved through papal support (Whitfield 1969). Yet this reading complicates the significance of Cesare’s example. As will be seen, for Machiavelli, the state Alexander VI helped him construct was not a cure for Italy’s political weakness, but another symptom of it. Although Machiavelli avoids dwelling at length on the origins or legitimacy of papal temporal power—a sensitive issue for someone who needed to preserve diplomatic relations with Rome—he nonetheless condemns the papacy as the chief obstacle to his political ideal: a united Italian state, strong enough to rival France and Spain and resist their expansionist ambitions. For Machiavelli, the Church was the principal cause of Italy’s political fragmentation. This is expressed clearly in the famous passage from the Discourses, where he argues that “The Church has kept, and still keeps, this province divided […] She is the reason why Italy […] has not a republic or a prince to govern her, only the Church […] not strong enough to occupy the whole of Italy, and not allowing anyone else to do so” (Machiavelli 1971a, p. 46).

As Machiavelli observed in Chapter XI of The Prince, before Alexander VI, “even the most insignificant lord and baron of Italy hardly rated the Church at all in temporal matters” (Machiavelli 1961, p. 40). Yet as early as 1488, during a discussion of the fate of Forlì and Imola following the death of Girolamo Riario, Lorenzo de’ Medici made a notable remark to the Ferrarese ambassador in Florence. He predicted that the time would come when the Roman Church would become stronger than Venice in Italy (Pastor 1911, p. 273). According to Machiavelli, Lorenzo’s warning began to materialise during Alexander’s pontificate, as Alexander, largely through the agency [instrumento] of his son, made papal power genuinely feared, unlike earlier popes whose authority had proved far less effective (Machiavelli 1961, p. 41). Guicciardini offers a similar picture in his Florentine Histories:

He [Cesare] acquired with great ease the lordships of the Romagna, the March, and the duchy; and having created a very fine and powerful state, the Florentines feared him greatly, the Venetians were suspicious of him, and the king of France respected him. Having assembled a strong army, he showed how great the power of a pope could be when he has a capable commander whom he can trust.

(Guicciardini 1931, pp. 264–65)

This context matters because Cesare’s campaigns were intelligible only within the military and political capacities of the Renaissance papacy. The atmosphere of crisis that had long plagued the Roman Church, particularly following the conciliarist crisis, justified extensive concessions to secular interests and fuelled renewed surges of libido dominandi. Above all, it enabled a new mode of legitimising and even sanctifying war. As D. S. Chambers has demonstrated, the Renaissance papacy developed a distinct ethic of conflict that may be described as papal warfare (Chambers 2006). By the fifteenth century, the Apostolic See had made the principle of the libertas Ecclesiae the bedrock of a formidable secular programme. This, in turn, came to coincide with the increasing Italian character of the Roman pontificate (Pellegrini 2009, p. 104). The line between the Church’s spiritual mission and the conduct of popes who increasingly appeared as secular princes presented a striking contrast even to contemporaries such as Guicciardini. He observed that papal concerns had become “armies and wars, wars even against Christians” (Guicciardini 1971, p. 414). At the same time, the religious framing of warfare remained central. An illustrative example is the prayer recited when Cesare was appointed Gonfalonier and Captain-General of the papal forces in March 1500. It invoked numerous biblical precedents recalling how God had aided His chosen people through the use of arms (Burchard 1885, p. 27). Although Machiavelli argued that ecclesiastical principalities rested upon “the ancient ordinances of religion,” he also emphasised the paradox that distinguished the popes as rulers in Italy: “they have states and do not defend them; and they have subjects and do not rule them” (Machiavelli 1961, p. 40). Cesare’s campaigns are thus best understood as the most aggressive extension of a broader papal military and territorial programme. From this perspective, Alexander VI’s political projects unfolded along an ambiguous trajectory. Although Alexander was driven by what contemporaries described as his “carnal attachment” to “give some place in Italy to his son” (Sanudo 1879b, vol. 2, p. 798), and was clearly eager to promote the greatness of his own family, his ambitions did not necessarily overturn the fundamental direction of fifteenth-century papal temporal policy. Like his predecessors, Alexander sought to expand papal territorial jurisdiction in central Italy and bring the barons of Lazio into obedience. In this context, Cesare acted as an extension of papal authority—a relationship clearly expressed in the ceremonial oath of loyalty he swore to his father, the pope, upon his investiture as Gonfalonier:

I, Caesar Borgia of France, Duke of Valentinois, Gonfalonier and Captain-General of the Holy Roman Church, from this hour forward will be faithful and obedient to blessed Peter, to the Holy Roman Church, and to you, my most holy Lord, Pope Alexander VI, and to your canonically elected successors.

(Burchard 1885, p. 29)

The broader context shows that Cesare’s military imprese were never acts of arbitrary power or mere adventurism. They were typically preceded by papal legitimation through the granting of vicariates and followed by the displacement of previous holders of delegated sovereignty. The Romagna, the most contested “ecclesiastical” region of the papal states, remained a mosaic of dominions formally held by papal vicars who behaved as independent rulers and no longer paid the apostolic tribute (Jones 1974, p. 150; Winter 2018, p. 40). Moreover, they had become increasingly dependent on external powers rather than on the Apostolic See since their de facto independence rested on the protection of the major Italian powers (Breisach 1967, pp. 172–74). The result was a political landscape in which Venice had emerged as the principal point of reference. It is therefore no coincidence that the first Borgia campaign was directed against Imola, Forlì, and Pesaro, ruled by the Riario-Sforza, an initiative welcomed both in Venice and by Louis XII. In order to pave the way for his son’s reconquest of the Romagnol territories, Alexander sent letters to the vicars declaring them deprived of their fiefs for failing to pay the required census (Burchard 1884, vol. 2, pp. 570–71). These developments show that only through French military assistance and Venetian approval could Alexander, in continuity with the policies of his predecessors, lay the legal groundwork for the removal of the vicars, then implemented manu militari by his son (Pellegrini 2009, p. 95).

As Enrico Angiolini has explained, Cesare’s “project” amounted to a technically coherent plan to create a personal dominion. This was a dominion legitimised through the traditional form of the apostolic vicariate and thereby rendered potentially hereditary. It was, in essence, a territorially homogeneous lordship based primarily on lands of the Church, governed and administered through ongoing political mediation with local elites (Angiolini 2003). The apostolic vicariate, moreover, represented the only workable model capable of withstanding the foreseeable turbulence following the death of the reigning pope. Nevertheless, this could only have been the case provided that a series of necessary conditions were met, conditions that ultimately failed to materialise.3 Additionally, although Cesare’s reforms sought to forge a more cohesive territorial state, they did so not according to an institutional model of a stately arrangement, but as part of a signorial dominion held under his vicarial authority. The creation of a Rota on the Roman model was certainly the initiative that came closest to demonstrating some aspiration towards “statehood.” Yet notwithstanding the fact that it held its first official session in the fateful summer of 1503, such projects had no opportunity to reach full maturity, owing both to Cesare’s continued financial reliance on the Camera Apostolica and its network of Sienese bankers, especially the Spannocchi and Chigi families, and, as will be seen, to his persistent military dependence on mercenary forces (Ait 2003, p. 63; Fantaguzzi 2012, p. 310).

Such a policy is evident from the outset. On 9 March 1500, almost three weeks before Cesare’s investiture as Gonfalonier and Captain-General (which took place on 29 March), Alexander granted his son the vicariates of Imola and Forlì (Alvisi 1878, pp. 468–69). When Cesare was then invested as Gonfalonier, this act was intended to further reinforce his legitimacy, particularly in light of Venice’s refusal to withdraw its protection from Faenza and Rimini. Given the strong Venetian interests in Faenza, ruled by the Manfredi, the Serenissima sought to counter Cesare’s legally grounded pretext, namely, the submission of “rebellious” vicars, by attempting to arrange the required payments through its own representatives in Rome (Alvisi 1878, pp. 68, 87, 116). From the beginning, therefore, the policy rested not only on legal legitimacy but also on the necessity of securing political guarantees. This concern is encapsulated in a remark Alexander made to the Venetian ambassador in Rome, Antonio Giustinian. By late 1502, the pope was repeatedly urging the Republic to ally with him to ensure that Cesare’s control over the Romagna would endure after his death. The pope told the ambassador, “you are immortal inasmuch as your Signoria never dies” (Giustinian 1876, vol. 1, p. 243). Recognising the vulnerability of his son, whose fortune depended on his own physical presence, in March 1503, Alexander declared that unless he could be assured that Venice would act as guardian of his son’s possessions, thereby providing the necessary security, “he would never die content” (Giustinian 1876, vol. 1, p. 450). Within this context, the term fortuna employed by Machiavelli in relation to Cesare’s standing reappears in his legation of 23 October 1502, during the critical moment of the Magione conspiracy:

As for affairs here and the condition of this lord’s state, since I have been here, it has been sustained solely by his good fortune [buona fortuna]. This has been due, above all, to the firm certainty that the king of France supports him with troops and the pope with money.

(Machiavelli 1875b, vol. 2, p. 120)

While the composition of Cesare’s army will be discussed in the following sections, it is useful first to examine the fiscal factors that linked him to his father and that, as Machiavelli underlined, constituted a vital foundation of his fortuna. If papal legality created Cesare’s position, papal finance sustained it in practice. As Machiavelli noted on 26 November 1502, Cesare had “spent more than sixty thousand ducats” since the beginning of October, a figure that Machiavelli reports had been confirmed two days earlier by “Messer Alessandro” [Spannocchi], who served as the duke’s treasurer (Machiavelli 1875b, vol. 2, p. 198).

At an earlier stage, Alexander had demonstrated his willingness to invest heavily in military expenditure. He initiated extensive improvements to Rome’s fortifications and to a broader chain of strongholds across the Papal States, stretching from Pesaro and Fano on the Adriatic coast to the southern frontier with Naples. Castel Sant’Angelo underwent significant strengthening works, while Civita Castellana—favoured by Alexander and strategically located along the Via Flaminia—was redesigned according to contemporary defensive innovations. These modifications were intended to improve resistance against the lighter, more mobile artillery introduced by the French (Company 2002, pp. 188–201, 287–350). This illustrates how military expenditure coincided with the expanding nature of the papacy, both as a military power and as a court. As the growing temporal responsibilities of the papacy required an increasing number of secretaries and curial officials, Alexander established a new secretariat in 1500 to manage diplomatic correspondence, which had become increasingly extensive (Richard 1924, p. 434). In September 1500, the twelve newly appointed cardinals paid approximately 150,000 ducats for their promotion, with individual contributions ranging from 4000 to 25,000 ducats, the latter paid by the Archbishop of Seville, Diego Hurtado de Mendoza (Burchard 1885, p. 77). Similarly, in May 1503, the creation of nine new cardinals led Giustinian to estimate that the red hats yielded “between 120,000 and 130,000 ducats; which, when added to the sums from the sale of the new offices, which are 64,000 ducats […] rises to a very large sum” (Giustinian 1876, vol. 2, p. 30). The interdependence between the creation of these cardinals and Cesare’s military campaigns can be seen in Sanudo’s account of the promotions of September 1500. He writes that the pope sent Cesare to the cardinals to tell them that through these funds “he can have money for the enterprise of the Romagna” (Sanudo 1880a, vol. 3, p. 855).

The argument, then, is that political ability and military effectiveness remained embedded within papal structures of legitimation, finance, and territorial jurisdiction. Without entering into the full complexity of subsequent grants and territorial adjustments, a 1502 financial record cited by Adolf Gottlob (Gottlob 1889, pp. 228–29) sheds light on the fiscal foundations of Cesare’s rule in the Romagna. It shows that Alexander granted the territories to Cesare on favourable terms while preserving papal property rights. In return, Cesare acknowledged the Apostolic See’s superior lordship (dominium eminens), maintaining formal papal sovereignty. An entry of 15 July 1502 records that Cesare paid an annual census of about 2300 florins for major centres including Forlì, Imola, Bertinoro, Rimini, Cesena, and Pesaro. These payments illustrate both Cesare’s fiscal obligations and the continued integration of his dominion within papal legal and financial structures. Archival financial records further indicate that between 10 May and 12 July 1502 the Camera Apostolica purchased substantial quantities of gunpowder, amounting to roughly 3324 ducats. Additional military costs incurred in May 1502 included 3750 florins for grain supplies and multiple payments for artillery amounting to 6370 florins (as noted in the liber artigliariarum, fol. 206). The final three payments were drawn from the private coffers of the papacy and included 16,320 ducats dispatched to Cesare on 17 September 1502, followed by a further 15,000 ducats transferred to him on 3 December of the same year. In late December, Giustinian claimed that, in the previous days, Cesare’s army had been consuming approximately 1000 ducats per day (Giustinian 1876, vol. 1, p. 297).4 Although not entirely exceptional, the military expenditures of the Camera in that year were therefore enormous.

These figures matter not only for their scale, but because they show that Cesare’s power depended on recurrent papal expenditure rather than on self-supporting military institutions. This dependence points to the broader political character of his dominion. Beyond the necessity of external support—papal legalisation and finance, and, as will be seen, French military backing—Cesare’s political position revealed the blurred foundations of a “secular principality” constructed upon the apostolic vicariate. The city lordships of the Romagna, formally held pro Sancta Romana Ecclesia, could indeed be entrusted to Cesare, who, as Alexander’s bulls repeatedly emphasised, had “spared neither expense, labour, nor danger” in subduing the “rebellious and disobedient” territories for “the honour and authority of the Roman Church.” In return for these “deeds and merits,” he received those lands within his duchy (Pagi 1748, p. 367). Nevertheless, Cesare’s principality was not intended to extend far beyond these limits. This remained the case even if his successful elimination of the Romagnol signori, together with the suppression of the Roman barons, effectively freed the papacy from its dependence on noble factions and shifted the balance of power in favour of the popes (Shaw 2009; Carocci 2012, p. 82).

Machiavelli provided a clear illustration of this situation on 2 January 1503, when he reported that Cesare had told him the following:

This lord said that he intended to liberate the territories of the Church from its factions and tyrants, and restore them to the pope, and retain only [solum] the Romagna for himself: and he judges that for this a new pope would be grateful [obbligato] to him.

(Machiavelli 1875b, vol. 2, p. 264)

Reflecting on this matter later, Machiavelli observed that upon the accession of Julius II, the new pope “found the Church strong, possessing all the Romagna, the barons of Rome reduced to impotence” (Machiavelli 1961, p. 41). Yet this strengthening of papal power stood in stark contrast to Cesare’s increasingly precarious position following Alexander’s death. Several factors are often invoked to explain the rapid collapse of Cesare’s authority. These include the loss of French support, the emergence of Giuliano della Rovere, and the interplay of fortune and ability. These factors ultimately reflect a single underlying reality: Borgia’s rule in the Romagna, despite strong papal backing, remained fundamentally a form of personal power. Moreover, the College of Cardinals was not yet under full Borgia control, making a reaction after Alexander’s death almost inevitable (Reinhard 2025, p. 333). Indeed, it was thanks to the Borgia-aligned cardinals that Alexander had established Cesare’s principality in the Romagna “with the approval of the consistory” (Guicciardini 1971, p. 446; Pellegrini 2002, p. 20). The same support also underpinned his subsequent, though ultimately unsuccessful, attempts to prevent its reversion to direct papal authority (Mallett 1987, pp. 252–60). In late October 1503, Machiavelli wrote that while Cesare was in Castel Sant’Angelo, several cardinals visited him, underlining his considerable control over the College, especially the Spanish cardinals. Nevertheless, he concluded that “it remains to be seen whether the duke will succeed in being favoured by the new pope” (Machiavelli 1875b, vol. 2, pp. 313–15).

With his father gone, Cesare had few alternatives. His only hope was to continue functioning as the military arm of an increasingly autonomous and militarised Roman Church. This represented his only viable means of preserving his political utility for future popes and thereby improving his chances of survival under the shadow of papal power (Pellegrini 2010, p. 260). Julius II ultimately exposed this contradiction by forcing Cesare to decide whether to prioritise his gonfaloniership or his duchy. As the new pope told Giustinian in November 1503, the lands of the Romagna “are ours mediate vel immediate; therefore whoever holds them, holds them as a vicar or feudatory of the Church” (Giustinian 1876, vol. 2, p. 279). The Borgia attempt to dominate the papacy, perhaps even to render it hereditary, ultimately produced the opposite effect, for Cesare’s principality was in fact only a contingent extension of papal power, sustained through a personal and ultimately revocable arrangement. The strengthening of the Roman Church under Julius II makes this point still more clearly: the same process that consolidated papal authority exposed the fragility of Cesare’s own dominion.

The rapid collapse of Cesare’s position after Alexander’s death was therefore not simply the result of misfortune or an unexpected political reversal. Because papal power was usually brief and unstable, and because new popes often created rival factions, any state founded on papal favour was bound to be fragile and short-lived. Machiavelli develops a related insight into the fortune of ecclesiastical principalities in Chapter XXIII of Book I of the Florentine Histories. There he observes that, “up to our times,” the only thing still lacking was for popes to attempt to leave the papacy itself to their relatives “as an inheritance.” Yet he also stresses that such dynastic projects had generally been short-lived, since popes usually lived too briefly either to plant them securely or, if they did plant them, left them with “so little and such weak roots [deboli barbe]” that, once the power sustaining them disappeared, “at the first wind, they broke” (Machiavelli 1888, p. 35).

Machiavelli clarifies the ultimate implications of dependence in Cesare acting as a “papal creation” when mentioning Alexander’s deeds in The Prince, “discussed above in the actions of the duke” (Machiavelli 1961, pp. 25, 41). Alexander, not Cesare, in this case, emerges as the true actor, since he is the one “to unsheathe the sword [trarre fuori la spada]” (Machiavelli 1961, p. 27). The argument does not end there, however, since Alexander too is shown to have acted as an instrument. As Machiavelli acknowledges, “although his intention [Alexander’s] was that of making great the duke rather than the Church”, the Church ultimately “inherited his labours [fu erede delle sue fatiche]” (Machiavelli 1961, p. 41). As Pocock observes, Machiavelli could never convincingly present Cesare as independent from “papal and curial politics” (Pocock 1975, p. 174). On this reading, Machiavelli did not seek to establish Cesare’s autonomy from the Church, since Cesare’s very failure in this respect reveals the depth of his dissatisfaction with his actions. This qualifies the claim that four years into his campaigns, Cesare had still not established “firm foundations,” that is, a military basis sufficiently stable and autonomous to survive the withdrawal of external support.

This complexity can be highlighted in the paradox that, for Machiavelli, Cesare’s conduct belonged to the realm of the azioni delli uomini grandi. Indeed, Machiavelli declares that he could offer no “better examples [esempi migliori]” for those aspiring to princely power, even though Cesare’s exceptional virtù ultimately failed to secure his state. This tension, noted by several critics (Sasso 1966; Dionisotti 1980), gives Borgia’s trajectory a distinctly tragic force. Before the conclave, on 28 October, Machiavelli could still report that “the duke is in the castle [of St. Angelo] and is more hopeful than ever of achieving great things” (Machiavelli 1875b, vol. 2, p. 308). Yet on 4 November, he reported that Cesare was refusing to recognise the imminent danger of the “natural hatred [naturale odio]” of the newly elected della Rovere pope (Machiavelli 1875b, vol. 2, pp. 327–28).

This leads to the attribution of Cesare’s fall to what Machiavelli termed an estrema malignità di fortuna (Machiavelli 1961, p. 23), thereby casting his example as a warning that even the highest political virtù may be overcome by fortune’s most violent assaults. The “perpetual fortune” that Machiavelli attributed to Cesare in June 1502 reappears in transformed form in Chapter VII. There, the crucial distinction is between one’s own fortune and the fortune of others. Cesare had acquired his state through his father’s fortune and lost it by the same means. This tension in Machiavelli’s assessment of Cesare—admiration during the years of Cesare’s success, followed by a harsher judgment after his collapse in late 1503—lies at the center of the paradox of Borgia as the model prince. It is here that Cesare’s “prescriptive” significance emerges in the form Machiavelli gave it. The proliferation of “alternative histories” in The Prince, strongly suggested by phrases such as “he would have succeeded had Alexander lived [li sarebbe riuscito, se Alessandro viveva]” (Machiavelli 1961, p. 26), reflects Machiavelli’s effort to show that something had gone awry in Cesare’s plan. Through this counterfactual logic, Cesare Borgia, who in 1513 unmistakably appeared as a defeated man, could be transformed into an exemplary model. The praise given to him earlier in Chapter VII and later in Chapter XIII is therefore not simply cancelled, but complicated. By associating Cesare so closely with fortuna—the very opposite of virtù as a secure foundation—Machiavelli silently undermines the overt praise of Borgia and calls into question the quality and durability of his virtù (Benner 2013, pp. xxi–xxii). As Raffael Ruggiero has maintained, The Prince can be read as a “masterpiece of ironic writing with a moral purpose” allowing one to read Cesare as a lesson in failure drawn from the “effectual truth of the matter,” one that is “useful to he who understands [utile a chi lo intende]” (Ruggiero 2016).

3. Between French Auxiliaries and Mercenary Arms

Cesare Borgia’s campaigns must be placed in the wider context of the guerre horrende d’Italia. Writing about a decade after Alexander VI’s death, Machiavelli observed in The Prince that Alexander, “more than any other pontiff who ever reigned, showed what could be done with finance and force of arms” (Machiavelli 1961, p. 41). This underlines that the Italian Wars created new opportunities for papal expansion, but only because the French alliance was indispensable from the outset. Yet French military backing and Orsini mediation were not merely initial supports that Cesare later transcended; they remained enduring conditions of his military effectiveness. His problem was not dependence on one external force alone, but on a shifting combination of auxiliaries, mercenary captains, and political intermediaries whose usefulness was inseparable from their unreliability. This qualifies Machiavelli’s later claim that Cesare came to rely on his “own” arms: what appears in The Prince as a movement towards autonomy looks, in the diplomatic record, more like a reconfiguration of dependence than its resolution.

As Guicciardini observed, with the outbreak of the Italian Wars in 1494, the fortune of the Italian peninsula changed decisively. He noted that from the outbreak of the wars, “foreign nations and barbarian armies have had the faculty to trample it and devastate it” (Guicciardini 1971, p. 74). Alexander himself had witnessed how Charles VIII descended into Italy and seized Naples “with a piece of chalk” (Laven 1995, p. 357). Following his retreat, however, French power in Naples collapsed. Yet the episode, culminating in the Battle of Fornovo, demonstrated how large foreign armies could enter Italy and withdraw from the peninsula with relative ease, thereby encouraging further interventions. The renewed invasion under Louis XII reshaped Italian politics so profoundly that Kenneth Setton and David Abulafia identify it as the moment of a “diplomatic revolution” (Setton 1976; Abulafia 1997, p. 255). By accepting the new state of events, and with the prospects of a formidable French presence in the north and south of the peninsula, Alexander favoured French intervention in Italy and disrupted the existing political order by endorsing the disorder on which his own project depended.

A commonplace assumption in Italian political thinking held that the French, though invincible on the battlefield, were poor administrators of their victories and therefore destined to lose territories with the same ease with which they had conquered them. A complementary assumption maintained that Venice, with its proverbial slowness in both decision-making and action, acquired territories gradually but rarely, if ever, lost them (Pellegrini 2009, p. 84). As Machiavelli later noted in Chapter VII of The Prince, the papacy could advance its temporal interests in the Romagna only because Louis XII’s accession to the French throne overturned the alliance system and led to the Treaty of Blois between France and Venice. Otherwise, “the duke of Milan and the Venetians would never have consented” to the papacy advancing its temporal interests in the Romagna (Machiavelli 1961, p. 23). Recognising that he could not achieve “any great thing” [cosa magna] independently, Alexander sought French support by approving Louis XII’s annulment and facilitating his marriage to Anne of Brittany. In return, Louis promised to support Borgia ambitions, offering the prospects of “lordship [signoria]” and “territories [stati] of the Romagna (Machiavelli 1971b, p. 943).” Although these lands were not formally his to grant, the agreement secured military backing, and Cesare, as Caesar de Francia, soon “made himself lord of Imola and Forlì under the banner of the three lilies” (Machiavelli 1971b, p. 944).

Machiavelli’s account of Cesare’s campaigns in The Prince highlights both the initial effectiveness and the structural limits of relying on external forces. Cesare’s early successes, he explains, depended on troops supplied by France and the support of the Roman Orsini family, a dependence that inevitably constrained his freedom of action. At this stage, the role of the Orsini within the papal army becomes crucial. Machiavelli identified the great baronial families as forming “a kind of association and secret pact [intelligenza],” treating war as their “profession [arte]” while avoiding decisive engagements (Machiavelli 1888, p. 49). Christine Shaw has shown that “money, marriage and force, rather than papal grant,” were the principal means by which these families accumulated their estates (Shaw 2009, p. 103). At the same time, their ambitions did not extend to the construction of a coherent stato; instead, they focused on consolidating control over castles, landed possessions, and jurisdiction over tenants and vassals (Shaw 2009, p. 101). During their conflict with Alexander in 1497, the Orsini proved highly effective in mobilising their supporters. They assembled forces strong enough to defeat the papal army in open battle and to capture the duke of Urbino, commander of the League. Although the Orsini were required to agree to a payment of 70,000 ducats to the pope and had to liquidate portions of their landholdings to meet this obligation, a substantial sum—40,000 ducats—was obtained from the ransom of the duke of Urbino (Shaw 1981, p. 7). These episodes illustrate how a powerful aristocracy, deeply rooted in the region around Rome, was capable of keeping the pope in a “state of torment” as Alexander complained (Carocci 2012, p. 82) and “weak and indecisive” as Machiavelli maintained (Machiavelli 1961, p. 41).

The relationship between Alexander and the Orsini, however, shifted when the pope aligned with France. The Orsini’s long-standing Guelf ties to the French crown facilitated reconciliation, and members of the family soon entered papal service. When Alexander recruited forces for his son, many of the Italian condottieri he employed were affiliated with the Orsini faction. In the spring of 1500, Paolo and Giulio Orsini entered into service agreements with Alexander, followed by Gianpaolo Baglioni in September 1500 and, in February 1501, by Francesco Orsini, the duke of Gravina, who left the service of Federico of Naples to join the Borgia. Carlo Orsini also served under Cesare for a time during that year (Shaw 1981, p. 11). These commanders were frequently present in Rome, where they consulted Alexander about the planning of Cesare’s campaigns. Given that Cesare himself spent only approximately ninety-five days in total with his army during the campaigns of 1499–1503, much of the strategic planning and practical execution of military operations rested with the Orsini condottieri (Cansacchi 1961, pp. 44–57). The limitations of depending on “mercenaries,” however, resurfaced once the Romagna had been secured, as Cesare’s ambitions to consolidate and expand his state were obstructed by the unreliability of his allies. The Orsini refused to support further campaigns, especially against Bologna, while King Louis XII intervened to restrain his operations against Florence. It was Paolo Orsini himself who, acting on Cesare’s behalf, had reached an agreement with Giovanni Bentivoglio; this settlement was then reinforced by a marriage alliance between Ermete Bentivoglio and the daughter of Giulio Orsini (Luzio 1914, p. 529). The connection later proved significant, since the condottieri who rebelled against Cesare were bound together not only by personal interest, but also by a shared Guelf political inheritance (Shaw 1981, p. 21). Only after these setbacks, and especially after the Orsini refusal to attack Bologna, did Cesare, as Machiavelli writes in The Prince, “determine no longer to be dependent on the arms and fortune of others” (Machiavelli 1961, p. 24). Yet the events that followed show that this decision did not resolve dependence but instead began a more desperate and unstable attempt to manage it. The question, therefore, is not whether Cesare recognised the problem of dependence, but whether his subsequent actions amounted to its resolution or merely to its reconfiguration.

Fearing Cesare’s growing authority, the Orsini and allied condottieri conspired against him, inciting rebellion in Urbino and “uprisings throughout the Romagna” that created “infinite dangers for the duke” (Machiavelli 1961, p. 24). Machiavelli emphasised that Cesare survived this crisis only “with the help of the French,” once again revealing his dependence on external forces. The issue, then, is not whether Cesare wanted to destroy his enemies, but whether he could do so through his own arms and virtù. As Machiavelli clearly implies, the answer is negative: he survived by relying on French arms and thus on l’armi d’altri. The First Decennale expressed the point more sharply, noting that, unable to counter his enemies’ attacks on his own, Cesare had to “cover himself with the shield of France [con lo scudo di Francia ricoprirsi]” (Machiavelli 1971b, p. 947). Although Cesare had by then reconstructed an army (discussed in Section 5), Machiavelli noted on 26 November 1502 that the subjects and soldiers of the duke of Urbino, following the agreement between Paolo Orsini and Cesare, were united and willing to fight for their ruler “as if the whole world was against them” (Machiavelli 1875b, vol. 2, p. 198). By contrast, Cesare was forced to expend considerable resources, whereas in the camp of Urbino “not a single coin was spent.” Machiavelli had already highlighted this imbalance on 20 October, when, discussing Cesare’s provisions and the expected French cavalry, he reported that since his arrival, Cesare had spent “so much money on cavalry and envoys as another lordship would not spend in two years” (Machiavelli 1875b, vol. 2, p. 109).

Although a French contingent of 450 lances had arrived in late November, later rising to over 600, the fragility of the foundations of Cesare’s position became especially clear when these cavalry forces left his camp for Bologna on 22 December. As Machiavelli tried to explain the sudden move, the French commanders Berry and Jacques de Clermont, Louis XII’s governor of Lodi, offered only partial explanations. They suggested that the withdrawal reflected concern for the local population, strained by French raids, and the belief that Cesare no longer required support. At the same time, the region, already burdened by the presence of numerous troops, was growing increasingly hostile to Cesare. Members of his own circle reportedly complained that “he could no longer tolerate” the French, and that “by keeping them, the arms of his friends caused him more trouble than those of his enemies” (Machiavelli 1875b, vol. 2, p. 246). Machiavelli ultimately judged that, with the withdrawal of the French contingent, Cesare had lost “more than half his forces and two-thirds of his reputation” [più che la metà delle forze, e a due terzi della reputazione] (Machiavelli 1875b, vol. 2, p. 247). This assessment captures both the numerical and symbolic effects of the loss, highlighting how closely Cesare’s military strength and political authority were tied to external support.

Combined with the severe financial constraints that Machiavelli had already highlighted, especially in contrast to the situation in Urbino, this withdrawal made the foundations of Cesare’s fortuna appear increasingly unstable. As Chapter VII of The Prince continues, recognising that he could trust neither the French nor “other outside forces,” Cesare responded with calculated violence, luring his opponents to Senigallia under the guise of reconciliation and eliminating them through “trickery” [inganni] (Machiavelli 1961, p. 24). Yet as Machiavelli continues, Cesare’s attempt to proceed on his own was owed to his ability to “dissimulate his spirit [dissimulare l’animo]”, granting to Paolo Orsini money, vestments and horses in order to lure his enemies into the trap (Machiavelli 1961, pp. 24–25). What this suggests is that the frequent use of the verb volgere [to turn; change] links his actions to the unpredictable turns of fortuna itself. Furthermore, a closer look at Machiavelli’s account of the inganno of Senigallia in the Descrizione del modo suggests that the text, often read alongside The Prince, is less laudatory than is generally assumed. The episode reveals above all the insufficiency of Cesare’s own arms, demonstrated by his reliance on the arrival of 500 French lances and by his inability to compel Florentine assistance. Far from resolving dependence, the Descrizione del modo shows how Cesare continued to operate within conditions of military vulnerability that he managed tactically but did not overcome structurally (Machiavelli 1813, pp. 391–99). All this, moreover, ran counter to Cesare’s own “design” to establish strong foundations [fondamento], a point that will be developed further below. As Machiavelli observed on 8 January 1503, Cesare’s success at Senigallia depended on stealth and “an unheard-of good fortune” [una fortuna inaudita], which, given its fickleness, did not augur well for his future (Machiavelli 1875b, vol. 2, p. 273).

As the Descrizione del modo further shows, Cesare could not afford to wait to achieve “complete victory”, given that the pope could die at any moment. He therefore had to seize the first “occasion [occasione]” that presented itself and leave much of the outcome to fortuna. The surviving text breaks off just as it begins to describe two possible ways in which such an opportunity to overcome the Florentines might arise. Either Machiavelli stopped writing at that point, or the continuation has been lost. As John M. Najemy has underlined, these final lines weaken the claim, attributed to Cardinal Soderini, that Cesare was a skilled judge of occasione and fully prepared to realise his ambition of conquering Tuscany and building a larger state (Najemy 2022, p. 34). As will be seen, that ambition was far less realistic than it appeared. In this imagined moment, Cesare appears instead to have missed the opportunity: his father’s approaching death made it impossible for him to wait for the proper moment to act. As in the legations and in The Prince, he remains dependent on fortune, on the arms of others, and on circumstances he never fully controlled.As Machiavelli wrote in January 1503, after the affair of Senigallia, Cesare became ever-more convinced of the need of Florentine support, even if his dispatches appear quite distrustful of these requests and on 8 January he maintained that “once he had carried out his enterprise against Siena, he will think that the opportunity he has planned and waited for has at last come” (Machiavelli 1875b, vol. 2, p. 274). That “opportunity”, as Machiavelli seems to imply, was to turn his armies against Florence. By that point, Cesare’s actions increasingly appeared to align with the reputation that had formed around him. Yet as Viroli has underlined, to grasp the real intentions of political leaders, one must be present at events, or at least close to them, gathering and weighing facts carefully. But uncertainty always remains, since political actors often deceive others, and sometimes themselves (Viroli 2014, p. 83). Interpretation is therefore necessary but never definitive: political judgments can always be challenged by rival accounts and alternative advice. As Machiavelli notes in The Prince, there is no higher judge to whom one can appeal for a final verdict [non è iudizio da reclamare] (Machiavelli 1961, p. 66). Machiavelli therefore presented many of his judgments as conjectural. During the sudden departure of the French troops from Cesare’s headquarters at Cesena in December 1502, as already seen, he admitted that “every man is making his own castles in the air,” and that even after every effort “to get to the truth of the matter,” no reliable truth could be reached (Machiavelli 1875b, vol. 2, p. 246). This difficulty was especially acute because princes deliberately concealed their intentions. Machiavelli learned this repeatedly during his years in Florentine service. Writing from Cesena on 26 December 1502, he observed that Cesare was “deeply secretive [segretissimo]” and that no one but the duke himself seemed to know what he intended to do (Machiavelli 1875b, vol. 2, p. 250).

Although Machiavelli’s dispatches show how difficult it was to assess and communicate Cesare’s intentions at the time, scholars have debated to what extent he later reshaped these impressions in light of subsequent events. Quentin Skinner, for instance, argues that Machiavelli’s view of Cesare was already fully formed during his diplomatic service and remained essentially unchanged when he returned to the duke in The Prince a decade later (Skinner 2000, pp. 9–10). Viroli, on the other hand, maintains that Machiavelli was not only a realist but a “realist with imagination,” one “keen to create political myths from the observation of political events” (Viroli 2014, pp. 66, 70). Certainly, Machiavelli later gave the events he had witnessed a powerful interpretive form. In the Discourses, without naming Cesare, he appears to endorse the kind of strategy used at Senigallia: “A man who uses fraud to overcome his enemy is praised, just as much as is he who overcomes his enemy by force” (Machiavelli 1971a, pp. 374–75).

This struggle between appearances and “effectual truth” can be witnessed in Machiavelli’s own writings from December 1502, which demonstrate that he was so convinced of Cesare’s “unstable” position that his original predictions proved incorrect. Observing Cesare’s precarious position, he warned the Dieci di balìa that Cesare might ultimately cast his lot with their enemies—the conspirators. Instead, Cesare moved decisively to eliminate them. He first ordered the arrest of Ramiro de Lorqua, his lieutenant in the Romagna, who was then dramatically executed in Cesena and subsequently exposed “in two pieces at the square” (Machiavelli 1875b, vol. 2, p. 250). Meanwhile, in Rome, Alexander maintained that Ramiro had been involved in the conspiracy, implying that this execution marked the opening move in the broader elimination of the conspirators (Giustinian 1876, vol. 1, p. 304). This broader context suggests that the exemplum offered in The Prince—according to which Ramiro’s elimination was intended solely to win the loyalty of Cesare’s subjects and, as Machiavelli later put it, to secure their “complete affection” [tutto lo amore] (Villari 1881, p. 364)—is far more complex than it first appears. If, as Harvey C. Mansfield suggests, Machiavellian political action requires the capacity to alter instruments, subordinates, institutions, and in this case “mercenaries”, when they become inconvenient, then Cesare’s case appears less as proof of achieved independence than as evidence of unstable and reactive power. Cesare could use Ramiro as an instrument of coercive rule and then discard him when his usefulness had ended; yet Cesare himself remained, in a deeper sense, the instrument of Alexander VI (Mansfield 1996, p. 291). His capacity to change subordinates did not free him from the larger structures on which his power depended.

The episode therefore reveals a hierarchy of instrumentality: Ramiro was Cesare’s instrument, but Cesare was Alexander’s. This complicates any reading of Cesare as autonomous even in such actions, since his power to “manipulate” others operated within a political order that he did not ultimately control. As Benner further maintained, Cesare’s elimination of Ramiro can thus be understood as an effort to reassert control and contain local dissent at a time when his “own mode” of arms was already showing signs of collapse (Benner 2013, p. 105). Seen in this light, the episode appears less a purely theatrical gesture of political consolidation than part of a wider strategic response to an immediate political threat. The significance of the episode for the present argument is that even this paradigmatic act of princely consolidation occurred under conditions of unresolved military dependence, not after their resolution. Furthermore, Machiavelli’s later recommendation that Cesare’s former lieutenant, Don Miguel de Corella, be appointed to command the emerging Florentine militia has generated sustained historiographical debate. Corella was described by Biagio Buonaccorsi as Cesare’s fidatissimo (Buonaccorsi 1568, p. 84), and by Guicciardini as “a most cruel, terrifying and much feared man” (Guicciardini 1931, p. 281). His proposed appointment is significant because it complicates any straightforward interpretation of buon governo in Cesare’s duchy, linking effective rule not only to administrative order, but also to coercion and fear.

Apart from policing the disorderly Romagna and commanding infantry forces, Don Miguel appears to have been Cesare’s trusted agent in the elimination of political opponents. The strangling of Alfonso of Aragon, Duke of Bisceglie and second husband of Lucrezia Borgia, in the Vatican on 18 August 1500, has been attributed to him and was allegedly carried out on Cesare’s orders. He was later sent to Orvieto to eliminate troublesome citizens, and in 1501 captured Piombino, governing it until April 1502. In the following months, he was linked to the murders of Astorre Manfredi of Faenza and Giulio Cesare Varano of Camerino, as well as to the brutal sack of Pergola and Fossombrone, and was the architect of the executions of Senigallia (Mallett 1987, pp. 186–87; Cerretani 1994, p. 303).

Machiavelli’s treatment of virtù here depends less on abstract moral definition than on examples that reveal how political action works. This is why Cesare’s use of Ramiro to pacify the Romagna, followed by his theatrical execution, becomes one of Machiavelli’s clearest illustrations of political cruelty. The episode leaves deliberately uncertain whether cruelty merely served Cesare’s virtù or formed part of it. It is precisely within this context that scholars, such as Mikael Hörnqvist, interpreted Corella’s recommendation as evidence of Machiavelli’s admiration for Cesare’s pragmatic recognition of the need for firm discipline (Hörnqvist 2002, pp. 177–79, 184). After all, as Lauro Martines has demonstrated, Renaissance legal theorists likewise recognised that emergencies could require extraordinary measures and the temporary suspension of ordinary legal authority (Martines 1968, pp. 410–12). Hörnqvist in fact underlines this in relation to Machiavelli’s recommendations for forceful action aimed at restoring obedience in territories Florence already claimed as its own. This logic is clearest in the Cagione dell’ordinanza of 1506, where Machiavelli argued that the militia should begin in the contado, rather than in the more unreliable distretto, given that its inhabitants depended on Florence and “recognise no other patron” (Hörnqvist 2004, p. 145). This is why Robert Black argues that Machiavelli’s policy reflected a strategy aimed at intimidating rival factions within Florence’s own divided government (Black 2014, p. 43). Although such a measure might appear contradictory to the notion of buon governo, the prevailing interpretation, as Yves Winter has argued, emphasises that, as attested by “the historical records—edicts, proclamations and testimony”—Cesare’s Romagna was, in fact, just and well governed (Winter 2018, p. 43). At a different analytical level, Najemy maintained that the “friendship of Romagna”, as further reflected in the true motive behind Ramiro’s execution, was more an “aspiration” than an accomplished reality (Najemy 2013, p. 544). Yet as Mansfield has argued, in Borgia, ferocity and virtù appear together, suggesting that political greatness may require qualities traditionally classed as vices. In this sense, Cesare is central to Machiavelli’s redefinition of political virtue: virtù must be judged by its effects, by the verità effettuale of political action, rather than by conventional moral standards (Mansfield 1996, p. 18).

During the late months of 1502 and January 1503, while following Cesare’s court, Machiavelli’s dispatches continued to present him as a figure marked by decisiveness and action, qualities closely associated with virtù. At the same time, it appears clear from Machiavelli’s writings that he was well-aware that Cesare had little to no realistic chance of becoming “lord of Tuscany.” When Cesare briefly entered Tuscany in May 1501, his immediate objective was not the conquest of Florence, an impossible feat due to Louis XII’s vetoes, but the securing of an alliance and employment as the city’s military captain. The Florentine chronicler Piero Parenti makes this clear when he writes that “for the security of his stato, Valentino wanted to ally with us and become our captain, because, needing the support of some power in Italy, he thought none more to his purpose than [Florence]” (Parenti 2005, vol. 2, p. 433).

Reporting on 13 November 1502, after a reconciliation between Cesare and the Orsini and Vitelli, Machiavelli observed that if anyone doubted the agreement because “the duke would find it distressing not to satisfy his desire to take Bologna,” the answer was that experience had shown him that “it is better to make an alliance that will endure than to seize a city that can’t be held” (Machiavelli 1875b, vol. 2, p. 173). The rebellions of Urbino had taught him that he needed “to think more about preserving what he has acquired [mantenere lo acquistato] than about acquiring more.” This was very different from the image of Cesare as a warlord poised for further territorial expansion such as his portrayal in the First Decennale, which states that after the taking of Urbino, Florence “stood with heart and soul suspended” at the threat posed by him and Vitelli (Machiavelli 1971b, p. 946). It shows that in late 1502, Machiavelli appears to have believed that Cesare was overextending himself, and far from admiring his ambitions, he warned that they exceeded his capacity to transform rapid conquests into a stable state. On 2 December, he even told the Florentine government that it might hope “the duke will begin to get used to restraining his desires and to realise that fortune won’t grant him all his wishes” (Machiavelli 1875b, vol. 2, p. 208).

Parenti also describes the defiant mood in Florence. Some citizens argued that, if in 1494 the Florentines “had not feared the king of France and his 30,000 soldiers,” they had even less reason to fear Borgia’s much smaller army. Wiser observers understood that Cesare was more dangerous than such rhetoric suggested, yet his position remained fundamentally dependent on France. When his troops plundered Florentine territory, Louis XII ordered him to withdraw and end the disorder. Parenti judged the behaviour of Cesare’s army in Florentine lands to be a “great error,” since “if he desired an alliance with us for the safety of his own state, he should have showered us with favours, not injuries” (Parenti 2005, vol. 2, pp. 438–51). The result, according to Parenti, was the “eternal” hatred of the Florentines. In light of this antagonism, the claim that Cesare might have succeeded in becoming “lord of Tuscany” had Alexander VI lived longer seems less an expression of Machiavelli’s own judgment than an echo of Cesare’s ambitions. Cesare was not militarily capable of seizing Florence, much less all Tuscany. What he consistently sought from Florence (as Alexander sought from Venice) was not submission but alliance: a form of support that would strengthen his own insecure position. He therefore remained dependent on assistance from others and never achieved the autonomy that Machiavelli associated with virtù (Najemy 2013, pp. 551–52). The elimination of the conspirators, particularly the Orsini, reveals still more clearly the complexity of the situation. It was not as straightforward as it later appeared in The Prince. Machiavelli himself provides an important clue to this complexity. When conflict had already broken out between Cesare and his Italian condottieri, in October 1502, Cesare spoke of Vitellozzo Vitelli as “only being good for ruining places with no defence” (Machiavelli 1875b, vol. 2, p. 105). Machiavelli, already greatly influenced by the humanistic interpretations of the superiority of native soldiers might have been led to believe that Cesare was a convert of such doctrines (Larner 1966, p. 255). Furthermore, when it came to Vitelli and Oliverotto da Fermo, both were executed during the very same night [ma venuta la notte] of the inganno di Sinigaglia (Machiavelli 1813, p. 399). When it came to the Orsini however, back in November, one of Cesare’s secretaries informed Machiavelli that “this Duke is compelled to spare part of the Orsini, because, when the pope dies, he will need to have some friends in Rome” (Machiavelli 1875b, vol. 2, p. 161). Shaw in fact argues that after the inganno di Sinigaglia, Cesare delayed the execution of Paolo and Francesco for eighteen days because he initially hoped to secure the gratitude of the Orsini by sparing them. Only when he realised that reconciliation was unlikely did he finally order their execution (Shaw 1981, pp. 15–16). This suggests that Cesare shared his father’s ambition for further expansion, even at the expense of the Orsini faction. Yet his actions in the months leading up to Alexander’s death in August 1503 suggest that he still sought to preserve the family’s broader support. Giustinian reports that Alexander, who had sent artillery from Castel Sant’Angelo for the campaign, was greatly irritated when Cesare refused to lay siege to Bracciano. This was because the fortress was held by Giangiordano Orsini, who was under the protection of the French king (Giustinian 1876, vol. 1, p. 423). Furthermore, although Cesare did lay siege to the important Orsini stronghold of Ceri, held by Giulio Orsini, he allowed Giulio to withdraw safely after its surrender in April 1503, having him escorted to Pitigliano, which lay outside papal territory (Giustinian 1876, vol. 1, pp. 463–73). Even the critical Guicciardini admitted that these terms “were sincerely observed” (Guicciardini 1971, p. 499). This episode illustrates that, while Alexander remained firmly committed to reducing the baronial families to submission once and for all, Cesare’s concerns about securing the future of his own principality led him to pursue a more cautious and pragmatic course. In this respect, his priorities diverged from his father’s broader objective of leaving to the papacy a “legacy that so many of his predecessors had striven for” (Giustinian 1876, vol. 1, pp. 425–26).

Yet, as the earlier case of Venice suggests, Alexander had already begun to recognise this tension. It was at this point that papal and familial interests had diverged in a significant way. The Orsini were ultimately saved from complete ruin by the death of Alexander. Furthermore, their continuing importance, in stark contrast to Cesare’s increasingly precarious position, is suggested by the fact that both the Spanish and the French competed for their services and those of the Colonna rather than those of Cesare (Giustinian 1876, vol. 2, p. 210). Perhaps assuming too much from the Orsini’s traditional Guelf loyalties, the French ambassador Louis de Villeneuve failed to match the Spanish offers. As a result, the Orsini contracted with Spain to provide a combined force of 500 men-at-arms (Giustinian 1876, vol. 2, pp. 237–38). Ultimately, in October 1503, Giulio Orsini and Fabio, the son of Paolo Orsini, concluded their condotte with the Spanish. This arrangement later enabled them to benefit from Spain’s victory and to recover their fortunes (Shaw 1981, p. 18). This further reveals the decline of Cesare’s military utility as a “soldier for hire” following the dismantling of the political and military foundations on which his authority had previously rested.

This section has shown that the move from French auxiliaries to the management of Italian condottieri produced a more unstable and politically demanding form of dependence, one that required constant negotiation and coercion. This, in turn, raises a further question: to what extent can Cesare be regarded as a “soldier for hire,” and what do the available figures reveal about his status as a condottiere and commander of a “mercenary army”? Answering it requires moving from political dependence in general to the concrete structure of Cesare’s military capacity.

4. A Soldier for Hire

A closer analysis of Cesare’s military capacity reveals a persistent pattern of dependence and places him in an unstable position between prince and military entrepreneur. By “soldier for hire,” I do not mean that Cesare was simply a condottiere in the conventional sense. I mean that even after acquiring princely office, he did not command a military apparatus that was fiscally self-sustaining or firmly rooted in his own territories. His armies continued to depend on external finance, foreign contingents, and captains bound by negotiated service relationships. In that sense, his princely status did not eliminate the mercenary logic of his military power; it merely reconfigured it.

When Cesare resigned the cardinalate in August 1498 to “become a soldier and marry” (Sanudo 1879a, vol. 1, p. 1054), it was the Franco-papal personal alliance, rather than any formal treaty, that secured his investiture as duke of Valentinois. The duchy provided him with an annual revenue of 20,000 francs and stipends for 100 lances, and this was the first step towards the construction of a lay principality (Pélissier 1895, p. 337). When Cesare accompanied Louis XII into Milan in October 1499, he acted under the king’s command, as his signature regius generalis locumtenens indicates (Pélissier 1895, pp. 186–87). Following the capture of Milan, and in line with papal neutrality, Louis honoured the agreement by releasing “300 lances5 under Yves d’Alègre at his own expense and 4000 Swiss under the Bali of Digione, paid by the pope” (Guicciardini 1971, p. 403). Burchard records that the Camera Apostolica borrowed 45,000 ducats for the campaign from the now French-controlled duchy of Milan, and that Cesare received the sum “in the name of the Roman Church” (Burchard 1884, vol. 2, pp. 570–71).

This first impresa was therefore, in large part, a papal military operation. Louis’s instructions to dependants such as the Commune of Bologna emphasised that Imola and Forlì belonged to the Church [dommaine de la dicte Ecclise] and referred to aid owed to Cesare as “our lieutenant” [notre lieutenant] (Alvisi 1878, p. 465). Likewise, the obedience of these cities was formally received by Cardinal Juan Borgia-Lanzol, acting on behalf of the pope (Mallett 1987, p. 180). Yet even with such formidable backing, the responses at both cities revealed the imbalance between offensive strength and defensive resilience. The sieges of Imola, Forlì, and, as will be seen, Faenza matter not only as episodes of conquest but also as tests of what Cesare’s army actually was. At the outset of the first impresa, Cesare sent Achille Tiberti ahead with 500 horsemen to Imola, where, on 24 November, he demanded the city “on behalf of the Majesty of the king of France and of the entire League” (Bernardi 1896, p. 16). While the city quickly opened its gates, the fortress, defended by only 180 men, resisted for nearly two weeks. Even French and Swiss military superiority, then, did not automatically bring about rapid surrender. When the castellan, Dionigi di Naldo, asked for negotiations, the garrison surrendered only on 11 December and on very honourable terms (Pieri 1952, pp. 391–92). A similar pattern emerged at Forlì. The city itself surrendered quickly, but the Rocca di Ravaldino resisted until 12 January 1500. The eventual success depended heavily on the French artillery train, which included five large cannon, one culverin, and eleven falconets (Fantaguzzi 2012, p. 190). Although the artillery opened two breaches in the fortress’s south-west wall on 9 January, the garrison held out. The falconets proved decisive because, while Caterina Sforza ordered earthworks to replace the damaged walls, their fire killed many of her engineers. Andrea Bernardi, who described these events, also provides figures for Cesare’s army, which he described as composed of “every nation” [ogni generatione] (Bernardi 1896, p. 246). When this army entered Forlì in December 1499, he reported the following:

According to what was reported to me, there were about 8000 among Germans, Swiss, and French; 2000 Spaniards and Gascons; which amounted altogether to 12,000. All these were men of arms. And then there were about 2000 more between friars, craftsmen, servants, and prostitutes, because these were many; so that in total they came to 14,000, as stated above.

(Bernardi 1896, p. 265)

Giuliano Fantaguzzi estimates that the paid infantry numbered around 7000 (Fantaguzzi 2012, p. 188). The situation becomes more complex when Edoardo Alvisi notes that the Swiss infantry who mutinied in January 1500 did so because “they had already served the duke as far as they were required under the king’s promise” (Alvisi 1878, p. 85). This complicates Guicciardini’s assertion that these troops were paid by the pope and underscores the limits of Cesare’s autonomy in advancing the temporal ambitions of the papacy. When Ludovico Sforza returned to Milan in early 1500, the recall of the French troops to Lombardy reduced Cesare’s forces to just 1000 infantry and 500 horse (Garner 1912, p. 146). In light of this, Machiavelli’s declaration in Chapter XIII of The Prince that the conquest of Imola and Forlì had been conducted largely through the work of gente Franzesi remains broadly accurate. Yet the more rigid transition from “auxiliaries” to “mercenaries” described in the chapter becomes less convincing when one considers the more complex composition of the army Cesare led during his second impresa.

The army that began the second campaign in October 1500 numbered roughly 10,000 men. Sarah Bradford calculates 700 men-at-arms, 200 light cavalry, and 6000 Spanish, Italian, Gascon and Swiss infantry (Bradford 1976, pp. 113, 135). This agrees with Bernardi’s number, who writes of “40 squadrons6 of well-armed men” [40 squadre de zente bene armata] commanded by Cesare’s Spanish and Italian captains along with another “8000 men” (Bernardi 1896, p. 311). This figure also corresponds to the army that Cesare brought into Tuscany in May 1501, since Parenti estimated that it consisted of 3000 cavalry, 5000 infantry, and 2000 venturieri (Parenti 2005, p. 438). In late 1500, according to a contemporary chronicler, the force Cesare brought to Cesena consisted of about 8500 infantry, of whom 7000 were salaried mercenaries, including 500 Spaniards. The cavalry numbered 3800, of whom 2500 were French and only 400 identified as borgiani, and thus under Cesare’s direct command (Najemy 2013, p. 545). Fantaguzzi provides some detail on the composition of the force by noting that Giannotto Francese, a constable commanding Gascon troops, passed through Forlì with 600 infantry and 50 horsemen (Fantaguzzi 2012, p. 235). Sanudo gives more detail on the composition of the army by stating that there were 1700 Spaniards and Swiss. He also suggests that there were 2400 mercenaries not organised in condotte, for a total of 6000 men (Sanudo 1880a, vol. 3, p. 965). Although Sanudo’s total7 does not match the other estimates, his account provides enough detail for proportional comparison.

In essence, the majority of Cesare’s forces still consisted of mercenaries and French troops, even where efforts were made to reduce the visibility of that dependence. The backbone of his force was the infantry which included the Spanish troops and the numerous corps under Baglioni and Paolo Orsini, whereas the artillery under Vitellozzo Vitelli originally numbered 16 pieces (Woodward 1913, p. 188). As Pieri estimates, the French army subsequently sent to assist Cesare at the insistence of the pope numbered 1800 cavalry and 2000 infantry, while the papal forces comprised roughly 2800 horse and 6000 infantry (Pieri 1952, p. 392). These figures suggest that, although there was an effort to reduce reliance on French troops, as noted by Marco Pellegrini (Pellegrini 2009, p. 97), and thereby allow Cesare to operate with greater autonomy, the French presence remained substantial. A contemporary assessment by the mercenary Guidarello Guidarelli, who served in Cesare’s army, likewise highlights the limits of Cesare’s confidence in his forces and offers a notably critical assessment of the army:

Moreover, that army is rather mediocre, particularly the infantry; fortune accomplishes everything: it takes the field, conducts sieges, brings up scaling ladders, engages in battle, and ultimately captures cities. As for Faenza, there is no experience.

(Spada 2019, p. 70)

As Woodward has underlined, although the Spanish infantry was regarded as the most reliable component of Cesare’s mixed force, they ignored the accepted Italian conventions of warfare and had already gained a grim reputation for cruelty towards defenceless neutral civilians (Woodward 1913, p. 188). The case of Guidarello Guidarelli likewise illustrates the challenges Cesare faced in maintaining discipline within his Italian military following. Guidarelli’s later idealised and heroic tomb in Ravenna obscures a less martial death: as documented by Augusto Campana, Guidarello was treacherously killed at Imola by a certain Virgilio Romano following a quarrel, after which Cesare had the murderer beheaded. The episode occurred while Guidarello was serving Cesare among the commanders assembled for the siege of Faenza (Campana 1930, pp. 17–21). The siege itself, fought between November 1500 and April 1501, further illustrates how indispensable French reinforcements remained. Earlier still, on 12 August 1500, Machiavelli reported that, although the pope was pressuring Louis XII to assist in the conquest of Faenza, it did not appear that “the king is greatly inclined, as it seemed to him that he has already done him considerable favors” (Machiavelli 1875a, vol. 1, pp. 147–48). Nevertheless, in November Louis dispatched 100 lances under Yves d’Alègre from the Milanese in order to maintain papal support, especially with regard to Naples (Machiavelli 1875a, vol. 1, p. 238). Despite being heavily outnumbered, the roughly 2000 defenders of Faenza endured continuous bombardment and severe shortages, yet continued to resist. Papal resources had been extensively deployed as Cesare’s treasurer Alessandro Spanocchi had to take a loan from Venice in order to pay the troops while Cesare also ordered artillery from Brescia in order to strengthen Vitelli’s companies (Sanudo 1880a, vol. 3, p. 1467; Bernardi 1896, p. 330). Guicciardini described the Faentine resistance in heroic terms, noting that the Franco-papal army could not even approach the walls, as the defenders had burned the surrounding houses and cut all nearby trees. As a result, with “great sorrow” [pieno di sommo dolore], as Guicciardini puts it, Cesare was forced to quarter his troops in surrounding towns (Guicciardini 1971, pp. 438–39). Following further papal pressure, additional French cavalry and 4000 Gascon infantry were sent between February and March 1501 (Woodward 1913, pp. 198, 203–4). With these reinforcements, Cesare attempted a decisive assault with a formidable artillery train which included heavy cannon. The chronicler Gregorio Zuccoli records that in mid-April, the fortress was struck by 1660 artillery shots (Valgimigli 1864, p. 200). Ultimately, however, surrender was forced not by bombardment itself but by prolonged hunger and thirst (Mallett and Shaw 2014, p. 57). Faenza capitulated on 25 April 1501, securing terms that were considered relatively honourable under the circumstances.

In describing the campaign of 1500–1501 in his First Decennale, Machiavelli wrote that Cesare and his troops achieved “astonishing feats [mirabil opra],” including “the rapid capture of Faenza” [espugnando Faenza in tempo curto] (Machiavelli 1971b, p. 945). This is, however, somewhat ironic because Machiavelli knew very well that Faenza’s resistance had delayed Cesare’s advance by several months. It suggests that Machiavelli later projected onto Cesare, ex post, a model of military effectiveness shaped by Florentine political concerns rather than by the full complexity of the historical record. This discrepancy suggests that Machiavelli’s later references to Cesare do not simply report military reality. They select, compress, and reshape events in order to produce a usable political example. Faenza therefore illustrates the central problem of Machiavelli’s later exempla: Cesare could appear militarily effective while still lacking the autonomous foundations that The Prince would later require. This also fits the pattern proposed by Benner, according to which Machiavelli’s ironic intent, which is recurring in his work, amounts to a “provocative use of [classical and historical] examples.”8 Hulliung likewise argues that Cesare was not simply a historical model, but “an abstraction” fashioned by Machiavelli from elements of both Greek and Roman thought and reshaped into a figure of his own making (Hulliung 1983, p. 192).

Read in such light, the campaigns of 1500–1503 confirm not the achievement of military autonomy, but the continued dependence of the “historical” Cesare’s successes on external aid. A most prominent example of the matter is certainly the imagined “redeemer” which was ought to liberate Italy from the “barbarians”. After all, the brutality which accompanied the war-torn peninsula shows that the French in Italy were feared not merely for their new methods of warfare, but above all, for the forms of “brutalisation” that accompanied them (Fournel 2024). Yet as Machiavelli knew, Cesare himself, as lieutenant of Louis XII, had participated in the Siege of Capua in July 1501, which was one of the most brutal sieges of the wars (D’Auton 1891, vol. 2, pp. 42–47; Burchard 1885, vol. 3, p. 152). For the purposes of the current argument, it suggests that Cesare, notwithstanding his precise role in the sack, could readily come to terms with this furia Franzese. After all, as Marco Pellegrini underlined, the Borgia policy, which was from the outset built on the alliance with France, can be summarised in the following statement:

The king of France aimed at making Duke Valentino his privileged interlocuter in Italy: he would have delegated to him the central part of the peninsula, to rule in agreement with the papacy, while France would have spread its dominion over the Po Plain and the south of the peninsula.

(Pellegrini 2009, pp. 99–100)

By late 1502, however, this policy was already being overtaken by the worsening Franco-Spanish conflict. Their struggle “to drive the other out of Naples” led Alexander to realise that 1503 would be decisive year for the political future of the Italian peninsula (Giustinian 1876, vol. 1, pp. 243, 245–46). In the First Decennale, Machiavelli writes how both the pope and Cesare, in light of the limitations which the French alliance was encountering, looked “for a new companion that could hand them other states, upon seeing that with the French, they couldn’t gain more” (Machiavelli 1971b, p. 948). As Machiavelli underlines, the Borgia policy, as from the start, still depended on foreign arms to “give” them states. This suggests that as seen in the cases of Forlì and Faenza, and in this case, Ceri, Cesare’s military effectiveness cannot be separated from the balance of force available to him at specific moments (Angiolini 2003, p. 166). During the siege of Ceri (March–April 1503), which should be read in the context discussed in Section 5, Giustinian recorded the following situation:

The duke’s men diminish every day from hardship; they leave the camp, all in very poor order, and so too their horses; and I understand that around Ceri (according to what some of ours who are in the camp report, and who come to Rome every day) there are no more than about 1000 men, between infantry and men-at-arms, who, however, are without horses, because for lack of fodder they cannot keep them in the camp.

(Giustinian 1876, vol. 1, p. 430)

As Giustinian continued, artillery again proved decisive, and led to the fortress’s surrender in April:

He [the pope] told me that the duke, from Sunday until yesterday, had continually fired about 800 artillery shots, almost as if in despair of the undertaking, and had ruined all the walls, ramparts, and houses. All the soldiers were frightened and said they wished to surrender so as not to be cut to pieces.

(Giustinian 1876, vol. 1, p. 464)

Cesare accepted Giulio Orsini’s submission with full honours and the pope told the ambassador that “Ceri has so far cost us 40,000 ducats, but we valued the honour more than the money” (Giustinian 1876, vol. 1, p. 465). As Guicciardini notes, the pope might have proceeded more enthusiastically because even the territories of the Savelli had surrendered (Guicciardini 1971, p. 499). This also underlines how the last months of Alexander’s pontificate were marked by both advances and limitations, especially because of Louis XII’s intervention in Borgia military operations in both Lazio and Tuscany. These limitations became even clearer as the pope gradually distanced himself from the French, particularly after the Battle of Cerignola. On 14 July 1503, Machiavelli wrote that “the duke of the Romagna gives money to his men-at-arms in Rome, but it is unclear whether he is on the Spanish or French side” (Machiavelli 1984, vol. 3, p. 5). As the critical contemporary Francesco Matarazzo put it, with the papacy behind him, Cesare “had all the flower of the soldiery in his armies, for all the captains of repute served under him” (Matarazzo 1905, p. 244). On a different analytical level, Michael Mallett pointed out that with papal backing Cesare did indeed succeed in mustering effective troops that undoubtedly gave a good account of themselves. However, as Mallett continues, Cesare never enjoyed a monopoly over the best Italian captains, which were concentrated first in northern Italy at the outbreak of the Second Italian War in 1499 and, from 1501–1502 onwards, in the Regno (Mallett 2009, p. 425). On the Spanish side, Gonsalvo de Córdoba depended substantially on Prospero and Fabrizio Colonna9, who commanded his cavalry and helped devise the formidable field fortifications that played a major role in securing the Spanish victory (Mallett 2009, p. 425). Their continued military importance also reveals the resilience of the Roman baronial houses, especially when contrasted with Cesare’s more precarious position, which, as seen, depended heavily on the volatility of papal power. Although Cesare had unleashed a fierce assault against the Colonna in the summer of 1501 due to the dynasty’s ties to Naples, achieving a convincing victory, it was not a decisive one (Pellegrini 2010, p. 257). As Shaw has emphasized, even the confiscation of their estates did not permanently destroy the barons’ power: upon the death of a hostile pontiff, they could readily recover from their previous misfortunes (Shaw 2015, p. 230). This helps qualify Mallett’s observation that “Cesare Borgia’s army was an effective military weapon for his limited purposes” and that the French in particular went to considerable trouble to aid him and secure his assistance (Mallett 2009, p. 425).

The wider context thus suggests that as Paolo Pieri underlined, Cesare’s successes occurred when the broader political situation favoured him (Pieri 1952, p. 383). This point was also acknowledged by Machiavelli in The Prince. In Chapter III, he writes that when the Cardinal of Rouen told him that the Italians did not understand war, he responded that had the French truly understood politics [intendere dello stato], “they would not have allowed the Church to reach such greatness [tanta grandezza]” (Machiavelli 1961, p. 12). The point, then, is not that Cesare’s armies were ineffective. On the contrary, they could be highly effective under favourable circumstances. What matters is that their effectiveness remained contingent on support structures that were not securely his. This is the sense in which Cesare occupied an intermediate position between prince and military entrepreneur: he exercised command, but not over an apparatus that had ceased to depend on others.

5. Romagnol Recruitment and the Limits of Armi Proprie

Following the argument set out in Chapters VII and XIII of The Prince, scholars had traditionally interpreted Cesare’s portrayal as a ruler who created a pioneering system of good government with his military policy regarded as the most significant aspect of it. According to this interpretation, while other Italian rulers of the time relied on the mercenary services of the condottieri, Cesare was said to have established a milizia di paese: a military force drawn from his own subjects. No aspect of his rule has earned him greater praise. Alvisi, who first fully developed the case for Cesare’s buon governo, observed that “Cesare armed his people, when until then, all the lords of Italy disarmed them” (Alvisi 1878, p. 387). Yet more recent scholarship has drifted away from this view, and this section argues that Cesare’s military policy did not amount to a stable militia, despite the fact that his supposed movement towards such a system has long shaped interpretations of the discourse of armi proprie which appears in Chapter XIII of The Prince. The forces recruited from Cesare’s own territories remained too limited, temporary, and heterogeneous to constitute a durable military foundation.

In June 1502, reports from Urbino by Machiavelli and Francesco Soderini described how envoys associated with the Vitelli and Pandolfo Petrucci of Siena sought to pressure Florence by overstating Cesare’s military strength. These reports reveal two points: Cesare’s army was smaller than claimed, and recruitment did not amount to a stable territorial system. Machiavelli and Soderini reported that Cesare had around 400 men-at-arms, 300 light horse, and 3000 infantry encamped nearby, with a further 2000 troops arriving from the Romagna under Ramiro de Lorqua. On this basis, the dispatch of 26 June suggested that, if combined with forces stationed in Tuscany, Cesare could field as many as “16,000 men,” with some estimates rising to “between 20,000 and 25,000” (Machiavelli 1875b, vol. 2, p. 14). Machiavelli, however, treated these figures with scepticism, regarding the higher estimates as exaggerated and politically motivated. Both Alvisi and John Garner agree that the army Cesare commanded at the start of the third impresa, which departed Rome on 12 June, numbered roughly 10,000 men. These included about 6000 infantry, 700 men-at-arms, and 2000 troops stationed in the Romagna (Alvisi 1878, p. 280; Garner 1912, pp. 197–98). Similarly, Giustinian confirms a substantial portion of this army when, on 15 June, he recorded that Cesare commanded 700 men-at-arms and “6000 well-paid infantry” (Giustinian 1876, vol. 1, p. 26).

The reference to the 2000 troops in the Romagna, together with the envoys’ description of recruitment, in which Cesare “summons many” and then “chooses the best ones [fa scielta delle migliori]” (Machiavelli 1875b, vol. 2, p. 14), has sometimes been interpreted as evidence of an emerging territorial militia. Yet Cesare himself made clear that this process did not involve a civic levy. As Soderini’s dispatch10 shows, Cesare emphasised his preference for “carefully selected soldiers [gente electa].” He further explained that “I make my companies from Italians and Transalpines, according to the availability of effective men [uomini da bene].” This account suggests that, despite appearances, Cesare’s forces were not drawn from a territorially grounded military system but from selective recruitment within the broader mercenary market. Fantaguzzi records that in April 1501 Cesare took into his pay 500 men from the Val di Lamone and “gave them each a breastplate, a halberd, and a pair of hose” (Fantaguzzi 2012, p. 252). A letter from February 1502 attests that Ramiro de Lorqua ordered Forlì to supply 500 mounted men to escort Lucrezia Borgia, suggesting some use of Romagnol cavalry as well (Sant’Angelo 2017, p. 115). This brings into focus the Romagnol militia, which Larner famously described as something that “has been more praised than described” (Larner 1966, p. 254).

As the above examples demonstrate, Cesare did make use of salaried troops drawn from the Romagna. Taken together, the evidence suggests, as Larner has argued, that native forces were incorporated in two distinct ways. On the one hand, there was the periodic mobilisation of local inhabitants through emergency levies, typically organised on the principle of “one man per household” [un uomo per casa], as recorded by Biagio Buonaccorsi (Buonaccorsi 1568, p. 65). Sanudo also records such an instance of recruitment from September 1500, when Cesare assembled men from Imola, Forlì and Cesena before his conquest of Rimini (Sanudo 1880a, vol. 3, p. 832). These levies appear to have been raised only in moments of acute need, such as during the siege of Faenza or the Magione conspiracy, and were often difficult to assemble, suggesting limited military effectiveness and were mostly useful for defending the territory rather than campaigning beyond it. This interpretation is supported by the terminology used to describe such troops: the term cerna seems to have carried the connotation of an individual with little or no experience in warfare (Larner 1966, p. 258). Yet this form of recruitment requires some more attention because its interpretation had led some such as Alvisi to interpret this move as grounds for Cesare’s buon governo, leading Romagnols to “defend and stand themselves for his [Cesare’s] honour” (Alvisi 1878, p. 387). Although Woodward developed Alvisi’s argument, he was forced to admit that the principle of un uomo per casa was already present in Umbria as early as the fourteenth century, and that Cesare himself had learned “much from the experience of the Vitelli and the Baglioni” when it came to military organisation (Woodward 1913, p. 312). Martin Hobohm noted that Machiavelli himself had reported to the Dieci di balìa in July 1499 that Caterina Sforza commanded two regiments of native infantry, one of which numbered 1500 men (Hobohm 1913, vol. 2, pp. 293–94). Yet as seen in the case of Umbria, this was not only a reality which interested the Romagna. It appears clear that even Florence considered such practices as normal (Sanudo 1881, vol. 5, p. 954; Chabod 1964, p. 331). It is true however that as Hörnqvist has underlined, although Florence had a long tradition of employing peasant militia from the contado, these bore almost no comparison to what Machiavelli was thinking: a permanent institution numbering thousands and eventually tens of thousands of trained troops, and with complete bureaucratic support (Hörnqvist 2002, pp. 152–54). Cesare’s case clearly did not fit the pattern.

Moving to the second form of recruitment, this appears on 8 October 1502, when Machiavelli recorded that Cesare had dispatched Miguel de Corella with funds to reorganise around 1000 infantry, while also authorising payments for a further 800 troops from the Val di Lamone. Unlike the emergency levies, these were paid troops serving on a more regular basis. In fact, it is likely that these 800 troops correspond to the same forces, later estimated at around 500 men, serving under Dionigi di Naldo, noted in Machiavelli’s report of 13 November (Machiavelli 1875b, vol. 2, p. 75; see Table 1 below). Table 1, which is based on Machiavelli’s appendix from his legation of 13 November 1502, also mentions contingents of Romagnol soldiers, and additional documentation confirms the continued employment of paid Romagnol troops after this date. For example, on 22 April 1503, Giustinian reported:

Table 1. Composition of Cesare Borgia’s Army in Machiavelli’s Legation of 13 November 1502.

Category	Commander/Unit	Number	Notes
Infantry	Don Michele [Corella]	600	Commander leader of the infantry
Infantry	Dionigi di Naldo	500	Romagnols
Infantry	Comandatore	500
Infantry	Maestro di Sala	500
Infantry	Romolino	400	Spanish commander relative of Francisco de Remolins, governor of Rome and later cardinal
Infantry	Lo Sgalla da Siena	300	Italians
Infantry	Grechetto	200	Italians
Infantry	Salzato the Spaniard	300	Spaniards
Infantry	L’Imola	200	Romagnols
Infantry	Giambatista Mancino	400	Italians
Infantry	Marcantonio da Fano	500	Romagnols
Infantry	Giannetto di Siviglia	150	Spaniards
Infantry	Mangiares	200	Spaniards
Infantry	Gascons and Germans	600
	Total infantry	5350
Men-at-arms	Don Ugo [de Moncada y Cardona]	50	Spaniards; Commander leader of the men-at-arms
Men-at-arms	Monsignor d’Allegri	50	Spaniards; Spanish commander not to be confused with Yves d’Alègre
Men-at-arms	Don Giovanni di Cardona	50	Spaniards
Men-at-arms	Raccolti de’ paesi suoi	50	Drawn from Cesare’s own territories
Men-at-arms	Conte Ludovico della Mirandola	40	Italians
Men-at-arms	Gentiluomini di casa	100	Household contingent
	Total men-at-arms	340
Light cavalry	Don Michele [Corella]	100	Presumably Romagnols
Light cavalry	Maestro Francesco da Luna	50	Mounted arquebusiers (scoppiettieri a cavallo). Italians
Light cavalry	Messer Rinieri della Sassetta and Gian Paolo da Toppa	100	Crossbowmen. Italians
Light cavalry	Conte Ludovico della Mirandola	40	Italians
	Total light cavalry	240
Additional men-at-arms	Guido Guaini (Vaini)	40	Romagnols
Additional men-at-arms	Giovanni da Sassatello	40	Romagnols
Additional men-at-arms	Lance spezzate	40	These were lances which did not form part of a condotta, but made up an independent lancia. In his legation of 4 November, Machiavelli wrote that these were commanded by the Sienese Baldassare Scipioni
	Total additional men-at-arms	120
Attached troops	Deserters from the Bentivogli	40	Crossbowmen

Source: (Machiavelli 1875b, vol. 2, pp. 174–76). Note: Machiavelli also records that many of these troops had already exhausted four to six days’ pay, that some units were geographically dispersed as far as Fano, and that further reinforcements were expected, including about 3000 Swiss. He also notes that the son of the General of Milan and Messer Galeazzo Palavisini had each been ordered to raise 100 men-at-arms, though both remained in Lombardy, while five companies of French lances were present at Faenza (discussed in Section 2). These figures therefore distinguish between forces effectively listed in the army and troops expected or stationed elsewhere.

I went to the palace and found the pope at the windows overlooking the square of Saint Peter, together with the duke, watching about 500 infantry from the Romagna, all dressed in the duke’s uniform and white doublets with his emblem on the chest, very fine-looking men, who were parading around the square to the sound of drums, with their banners carried in front.

(Giustinian 1876, vol. 1, p. 487)

This report confirms the continued presence of paid Romagnol infantry, but it does not show the existence of a self-sustaining territorial army. At the same time, as Larner has shown, the lords dispossessed by Cesare had already been organising their subjects into military units. This suggests that local recruitment was not the sporadic practice implied by more traditional historiography. The case of Faenza is especially revealing: in the Val di Lamone, the arming of the Manfredi’s subjects had been explicitly prescribed by statute. Although such arrangements included temporary levies, Larner has emphasized that the states of the Romagna possessed their own paid, more permanent troops, composed of locals, long before Cesare’s arrival, and that “he [Cesare] established nothing new or revolutionary” (Larner 1966, pp. 263–67). As will be seen, the evidence indicates that Cesare never abandoned the use of condottieri. His army continued to be a mercenary army sustained by papal finance.

Returning to October 1502, Machiavelli recorded that Cesare had recently reviewed 6000 infantry selected from his territories, “which he can summon in two days” [i quali in due dì può avere insieme] (Machiavelli 1875b, vol. 2, p. 76). This figure, however, likely referred to the first instance of recruitment discussed above and thus represented a temporary levy rather than a standing territorial force. It is therefore probable that these men were not recalled once Cesare organised his new army, which, as will be seen, continued to rely primarily on mercenary forces. This distinction is crucial: neither form of recruitment amounted to the stable territorial military institution implied by Machiavelli’s later language of “own” arms. This suggests that the real innovation lay not in the creation of a permanent militia, but, as Cesare himself admitted when he spoke of “carefully selected soldiers,” in recent technological developments. This is particularly evident in the growing use of firearms, as Mallett has demonstrated (Mallett 2009, p. 253). As these innovations spread, mounted arquebusiers became increasingly common, and their employment by the Vitelli suggests that Woodward’s earlier claim that Cesare learned “much from the experience of the Vitelli” fits a broader pattern of military incorporation. Cesare himself came to maintain a unit of about 50 mounted arquebusiers, commanded by Francesco da Luna (see Table 1 below). This method of recruitment is also confirmed by Sanudo who records Niccolò Balbi’s assessment from December 1503, which states “from the Valle [di Lamone], 1000 good schioppettieri could be raised at little cost; moreover, there are forty professional soldiers, the best which can be found in Italy, who could train 1000 men; you just need to give them the schioppetti.” (Sanudo 1881, vol. 5, p. 504).

In early October 1502, alongside the 6000 infantry already mentioned, Cesare ordered the recruitmsent of 500 Gascons and the levy of 1500 Swiss, while couriers were continually dispatched to Rome, France, and Ferrara. Writing on 9 October, Machiavelli reported that Cesare possessed a well-organised artillery11, “as almost all the rest of Italy.” Nevertheless, he added that “on the other side, his enemies were armed and ready to attack immediately” (Machiavelli 1875b, vol. 2, p. 76). Machiavelli believed that Cesare could retain control of the Romagna “with the forces he had,” but only if he continued to receive external support, or “favours,” from others. In practical terms, this meant ongoing reliance on outside manpower and financial resources. Despite these efforts, Machiavelli shortly beforehand estimated that Cesare’s available forces remained limited: three companies of lances under Spanish captains, no more than 2500 paid infantry and roughly 100 lances of his gentiluomini, equivalent to just over 400 effective cavalry (Machiavelli 1875b, vol. 2, p. 75). In the following month, on 8 November, Machiavelli observed that, aware that the pope could die at any moment, Cesare understood that he “must establish strong foundations [fondamento] if he wishes to maintain the states he has acquired.” Machiavelli then underlined that “the first foundation he relies on is the king of France; the second, on his own arms [sulle armi proprie]” (Machiavelli 1875b, vol. 2, p. 160). Machiavelli’s appendix to the legation of 13 November 1502 allows this claim to be tested directly because it shows what Cesare’s army actually looked like at the very moment when Machiavelli once again speaks of Cesare’s “plan” [disegno] to turn to his “own” arms [stare armato d’arme sue].

The figures do not show the emergence of a self-sufficient territorial army. They instead show a composite force in which native contingents remained secondary, partial, and embedded within a broader structure of hired and externally supported arms. Taken together, the total12 number of infantrymen (5350) reflected Cesare’s earlier estimate of the forces his condottieri could assemble. Yet the infantry composition alone, even without counting the anticipated 3000 Swiss, makes clear that these forces did not constitute a unified, locally rooted militia. The appendix and subsequent recruitment imply that a substantial part of the infantry, as calculated by Larner, can be broken down into around 1050 Spaniards and 1200 Romagnols. Although the appendix makes it difficult to calculate the total number of transalpine troops, Machiavelli wrote in late December of 2500 Swiss, Germans, and Gascons, and of roughly the same number of Italians from outside the Romagna (Machiavelli 1875b, vol. 2, pp. 247, 250). Among the men-at-arms (also known as elmetti), 150 were certainly Spanish, while the light cavalry appears to have consisted largely of Italians; Larner speculates that those under Corella were Romagnols (Larner 1966, p. 260). Of all the men-at-arms, then, as the appendix implies, apart from the gentiluomini di casa, and the total number of Romagnols being 130, only 50 were certainly raccolti de’ paesi suoi [drawn from his territories]; the rest were either foreign or mercenaries. This distinction between one’s “own arms”, and “foreign arms” and “mercenaries” can be clarified by looking more closely at the infantry composition, which reveals a key detail. For instance, the 200 men under l’Imola and the 500 under Marcantonio da Fano were presumably composed largely of Romagnol troops, since both commanders operated within the Duchy of the Romagna. Thus, although commanders such as these, together with Dionigi di Naldo, Taddeo della Volpe, Giovanni de’ Sassatelli, and Guido Vaini, could be considered “local” figures, at least two of them were certainly, and the others likely, professional condottieri (Larner 1966, p. 259). These Romagnol contingents were also likely to have been those recruited on a regular basis. This shows that there is some truth in the claim that command was left in the hands of captains of the Romagna, where according to Alvisi, Cesare’s “confidence in his fortune was greater” (Alvisi 1878, p. 321). Nevertheless, the fact that most were condottieri shows that Cesare never truly abandoned his reliance on mercenary forces, while overall command appears to have remained predominantly in Spanish hands. Machiavelli had in fact described Ugo de Cardona as “leader of this lord’s men-at-arms”, and Miguel de Corella as “leader of his infantry” (Machiavelli 1875b, vol. 2, p. 80).

By the end of December, estimates of Cesare’s army differed in detail but remained broadly consistent. Giustinian reported that Cesare commanded 400 men-at-arms, 600 light cavalry, and 6000 infantry (Giustinian 1876, vol. 1, p. 297). Sanudo, however, placed the numbers slightly higher, recording “800 lances, 800 light cavalry, and 7000 infantry” (Sanudo 1880b, vol. 4, p. 586). Yet the force that encamped near Viterbo in February 1503 shows how the composition of this army was once again mostly dependent on foreign troops. Giustinian writes that, apart from 600 men-at-arms and 600 light cavalry, there were 4000 infantry divided equally between 2000 Germans and 2000 Gascons and French (Giustinian 1876, vol. 1, p. 391). Sanudo, on the other hand, says that the contingents of Gascons and French were actually 4000 strong (Sanudo 1880b, vol. 4, p. 740). Discrepancies in numbers at this point may be explained by Cesare’s ongoing recruitment efforts, noted by both Sanudo and Giustinian. Both sources more or less agree that these included 700 infantry from Narni and 1500 from Spoleto, or 1300 according to Giustinian (Sanudo 1880b, vol. 4, p. 733; Giustinian 1876, vol. 1, p. 391). Giustinian adds further detail, observing that these troops, drawn from the Orsini faction, would march reluctantly, since the presumed target of the campaign was Bracciano, a stronghold associated with their allies (Giustinian 1876, vol. 1, p. 391). Despite these Umbrian levies, and notwithstanding their questionable loyalty, Cesare’s army appears to have remained predominantly composed of mercenary and foreign troops. The army Cesare controlled in July, and thus shortly before his father’s death, according to Giustinian, was the following:

The number of his forces is reported to be 700 men-at-arms, 600 light cavalry, and 5000 infantry; nevertheless, those who have tried to understand the truth more carefully, counting their captains and what each has, both on foot and on horseback, find no more than 500 men-at-arms, and even those poorly equipped, 600 light cavalry, and 4000 infantry.

(Giustinian 1876, vol. 2, p. 81)

The main point here is that, quite apart from the diminution of his army, the Florentine chronicler Bartolomeo Cerretani observed that even after Alexander’s death on 18 August 1503, Cesare continued to recruit mercenaries, suggesting that he still lacked a sufficiently stable military force (Cerretani 1994, pp. 323–24). Indeed, Sanudo mentions 2000 Spaniards who entered Rome in September and also writes of 5000 Gascons (Sanudo 1881, vol. 5, pp. 77, 106). Giustinian also refers to 2000 infantry that the “duke recalled from the Romagna,” suggesting that these infantrymen were the Spaniards mentioned by Sanudo (Giustinian 1876, vol. 2, p. 160). Machiavelli and Giustinian vividly describe the months following Alexander’s death, underlining how precarious Cesare’s position became once he lost papal backing, as distinct from the more gradual diminution of his forces in the preceding months. Machiavelli writes that when Cesare left Rome in September to Nepi, where, gravely ill, he “threw himself in the arms of the [French] king”, he had 400 men-at-arms, 400 light horse, and 3000 infantry (Machiavelli 1984, vol. 3, p. 41). Upon Gonsalvo de Córdoba’s order that Spanish troops should march south, Cesare dismissed 200 lances and two of his captains, while under the terms of his latest agreement with Louis XII, he also sent 100 lances to the lord of Mirandola to serve with the French. These reductions further exposed his continuing, and indeed growing, dependence on more powerful allies (Najemy 2013, p. 548). When in November, and thus after the election of Julius II, Cesare sought a safe-conduct from the Florentines, Giustinian reported that his available forces had diminished dramatically to only 100 men-at-arms, 200 light cavalry under Miguel de Corella, and between 500 and 600 infantry (Giustinian 1876, vol. 2, p. 294). The mention of the Spaniards coming from the Romagna also fits the pattern given by Sanudo, who relates that the majority of the garrisons of the Romagna that held out were manned by Spaniards. This already makes clear how the difference between “local troops” and “foreigners” was not as clear-cut as the situation of Cesare’s “own arms” itself suggests. Resistance in these rocche was almost entirely owed to Cesare’s Spanish fidelissimi.13 The language of his “own” arms therefore risks obscuring a more complicated reality: Cesare did seek to reduce dependence on others, but the forces available to him remained too composite and contingent to justify speaking of an autonomous military foundation in any strong sense. What survived after Alexander’s death was not a self-sustaining territorial army, but a shrinking composite force whose most loyal elements were still disproportionately foreign, above all Spanish.

All this shows that, with papal wealth at his disposal, Cesare was effectively able to command much of Italy’s available mercenary manpower, and that these forces, together with his French allies, made up by far the largest part of his army. This is why his greatest strength eventually proved to be his greatest weakness. After Alexander’s death, Cesare had sent Cardinal Francesco Borgia to meet Prospero Colonna, hinting at a rapprochement with the Spanish. However, Cesare himself moved to join the French army at Nepi. This shows how the reduction of the army further weakened Cesare’s position and underscored his growing reliance on stronger allied powers. More dangerously still, this dependence extended to his own person. Machiavelli noted this on 10 September in his letter to Giovanni Baptista Ridolfi, after reporting that Gianpaolo Baglioni had returned to Perugia. Observing that Baglioni’s return had further diminished Cesare’s stati and partigiani, he noted that “if the French don’t grab him once again from the hair, he’ll have nothing left.” (Machiavelli 1984, vol. 3, p. 46). Cerretani underlines this when he writes that, while Cesare sought to resolve his disputes with the Orsini, the infantry he had only recently recruited, “seeing that Valentino’s fortunes were declining”, refused to continue following him (Cerretani 1994, p. 326). As a result, after the death of his father, Cesare found himself in a position similar to that of the former lords of the Romagna whom he had once overthrown: a relatively minor figure caught between far stronger external powers. More importantly, he was now exposed to the shifting dynamics of larger political forces operating beyond his control, which could easily sacrifice him for their own strategic interests. In this context, Pope Julius II initially considered using Cesare as a tool against Venice, only to discard him once he was no longer useful. When Cesare was subsequently imprisoned by the Spanish monarchs and sent to Spain, the move was designed to preserve good relations with the new pope. After escaping to Navarre, Cesare entered the service of his brother-in-law, John III of Navarre. According to Jerónimo de Zurita, when King John appointed Cesare captain-general of the army assembled to besiege the fortress of Viana, the force under his command comprised 200 light lances, 130 men-at-arms, and more than 5000 infantry, together with two cannon, two demi-culverins, and other field artillery (Zurita 2005, bk. VII, chap. LI). Tasked with suppressing the rebellion of the Count of Lerín, Louis de Beaumont, Cesare was killed during the Siege of Viana in March 1507—fighting, as he had been from the beginning, as a soldier for hire. The trajectory of his career therefore closes the argument as decisively as it began: Cesare died not as the founder of an autonomous military principality, but still in the service of another ruler.

6. Conclusions

Rather than confirming Cesare Borgia as the fully successful “new prince,” the historical record reveals a ruler whose political ambition outstripped his military and institutional foundations. His rise depended on papal finance, French military backing, and the services of mercenary captains and intermediaries. These same conditions, however, also made his power structurally fragile. Read against Machiavelli’s legations and other contemporary evidence, Cesare’s career demonstrates not the secure acquisition of “arms of his own,” but the limits of a principality built on external, negotiated, and revocable support. The forces at his disposal remained heterogeneous, heavily reliant on foreign troops, and organised through service relationships rather than durable territorial institutions. His “arms” were therefore not fully his in any strong institutional sense. They remained a composite force, and once these supports weakened after the death of Alexander VI, the apparent solidity of Cesare’s stato dissolved with remarkable speed. His collapse is therefore best understood as evidence of a broader structural problem: the absence of durable armi proprie.

This reading clarifies Machiavelli’s larger political argument. By presenting Cesare as both exemplary and ultimately vulnerable, Machiavelli transformed a historically contingent figure into a theoretical demonstration of the necessity of military autonomy. Cesare’s significance within Machiavelli’s political thought lies precisely in this tension between historical contingency and political prescription. His achievements suggested the possibility of a new political order, but his reliance on external forces prevented its consolidation. Cesare thus emerges less as a model to imitate than as a warning to heed: without “arms of one’s own,” even the most ambitious prince remains vulnerable to the very forces he seeks to command.

This tension lies at the heart of Cesare’s status as Machiavelli’s model prince. Writing The Prince six years after Cesare’s death at Viana, in Chapter VII, he acknowledges that “there was such ferocity and such virtue in the duke, and he knew so well how men have to be won over or lost” (Machiavelli 1961, p. 27). Yet these qualities did not preserve his state. Notwithstanding the alleged transition from auxiliaries and mercenaries to armi proprie in Chapter XIII, there was no “linear” development of such a move since Cesare ultimately remained dependent on “the arms and fortune [fortuna] of others” (Machiavelli 1961, p. 24). Cesare therefore emerges not as a straightforward model for a “new prince” seeking to conquer and preserve a state, but as a “negative” model: a ruler whose virtù could not free him from “the original sin of dependence on his father and on the French” (Najemy 2013, p. 555). Cesare’s value for Machiavelli lies precisely in this tension. He shows both the necessity of founding power on one’s own arms and the danger of trying to construct those arms only after power has already been acquired through fortune and the support of others. The “negative” outcome of this apparent exemplar can therefore be read as part of Machiavelli’s method: Cesare is praised in terms that are later undermined by the “effectual truth” of his failure. Machiavelli’s statement in Chapter XVIII that, in the actions of princes, “one looks to the end” can thus be read as a retrospective judgment on Cesare’s career (Machiavelli 1961, p. 66). However impressive his courage, audacity, and military ability may have appeared, Cesare ultimately failed to maintain his state [tenere lo stato]. Cesare Borgia thus matters not because he confirms Machiavelli’s category of armi proprie, but because he exposes the distance between a historically contingent case and the theoretical exemplar that Machiavelli later fashioned from it. Read in this way, the question is shifted from whether Machiavelli accurately described Cesare’s army to how Machiavelli used Cesare to think through the humanist problem of exemplarity: the transformation of historical action into political instruction.