Despite Being Spanish by Birth: Cesare Borgia of France and Duke of the Romagna

Abstract

This article attempts to underline the wider context of Cesare Borgia’s imprese; the product of Alexander VI’s dynastic designs, which went hand in hand with the aspirations of the Renaissance popes to incorporate those territories which belonged to them. Drawing on several published primary sources and recent scholarship, this article will seek to examine how political and diplomatic agreements shaped the development of Cesare’s career. These factors will help illuminate Cesare’s position and show how the definition of the Renaissance papacy as a ‘two-faced Janus’ can be extended to encompass the ‘peculiar’ nature of Cesare himself, the secular arm of an increasingly militarised and autonomous Roman Church and a duke in his own right, who nevertheless remained dependent on papal favouritism and French support. Together, these considerations will offer insight into the political characteristics of the Renaissance Papal States, particularly during the early Cinquecento.

1. Introduction1

In October 1502, Pope Alexander VI told the Venetian ambassador Giustinian: “Despite being Spanish by birth, and in some respect we show favour towards France, we are however Italian; and it is here that we have to learn to live, like our duke.”2 This declaration is highly significant for understanding the political policies of the pontificate of Alexander VI (1492–1503). It sheds light on how the Borgia, a Spanish family, rose to the pinnacle of the ecclesiastical hierarchy, and how through agreements with France, the pope managed to both aggrandise his son Cesare Borgia and bring under the Roman Church’s authority those territories which legally belonged to it. A definition of the Renaissance Papal States which has gained wide acceptance is that of Paolo Prodi who defined them a ‘two-faced Janus’ (Prodi 1982, p. 49). In this article, I propose to extend this definition to Cesare himself, by drawing on published primary sources and recent scholarship that illuminate such a theme. Cesare’s military and political achievements can in effect be inserted within a process of connections which permitted him to implement the ambitions of the papacy as its secular military arm. At the same time, he operated as a signorial duke in his own right, though his position remained fundamentally tied to papal favouritism and French support. Cesare’s figure must therefore be inserted within the broader political theatre of the European monarchies, particularly in relation to the interests of the Valois and the Spanish monarchs in the Italian peninsula. The Italian Wars opened new horizons of power that shaped these dynamics, securing Cesare’s position as a product of emerging alliances and negotiations; those very conditions that informed Machiavelli’s reflection on the principe nuovo. This article will thus attempt to offer a careful examination of Cesare’s position within the framework of the Italian political scene, situated between the papacy and France, and to show how these forces complemented and converged. It will also assess the extent to which Cesare’s political experience is relevant to the broader political history of the Papal States in the early Cinquecento.

2. The Roman Church and Alexander VI

It is with Machiavelli that one can begin to speak of Italy as a political space, expressed in the term cose d’Italia (Chabod 1979). This provides a useful starting point for understanding the political environment in which Cesare operated and which contributed to his standing as the archetypal ‘Renaissance Prince.’ As Machiavelli noted around a decade after the death of Alexander VI, the papacy’s temporal power had generally been little respected in Italy, until “Alexander came to power, and he, more than any other pontiff who ever reigned, showed how a pope, with money and military force could prevail.”3 As Machiavelli also maintained in The Prince, the political situation of the Holy See both reflected and intensified the broader fragmentation of the Italian states, whose chancelleries were principally concerned with maintaining a balance of power among them:

Before Charles, king of France, came down to Italy, this province was under the power of the pope, the Venetians, the king of Naples, the duke of Milan, and the Florentines. These powerful states had two principal aims: one was that of preventing foreigners from entering Italy under arms, the other, that each one of them possessed more territory.4

The descent (calata) of Charles VIII in 1494 marked a decisive watershed in the political fortunes of Italy. Earlier episodes of foreign intervention now gave way to full-scale armed interference, a process that would not fully conclude until 1559. For the political aspirations of the Holy See, the momentous changes to the Italian state system brought about by the Italian Wars ultimately assisted the popes in strengthening their control over the Papal States. Although for Machiavelli these contemporary guerre horrende d’Italia provided a negative perception of the modern state of things, he still upheld the ideology of the latin sangue gentile which maintained a sort of continuity of the ‘greatness’ of the past. This is something which is clearly reflected in his reference to Petrarch’s Italia Mia, a poetic plea which Machiavelli envisioned as a political reality at the end of The Prince (Machiavelli 1961, p. 99). Machiavelli believed that the modern world suffered from a lack of virtù because it had lost touch with the virtues of a ‘great past.’ If for him, this rupture was largely due to the Christian ethic that shaped the modern era, the Holy See likewise shaped the destiny of the Italian peninsula. This was mainly because as opposed to the other Italian principalities, that which distinguished the Holy See was its ability to attract ‘foreign’ alliances through its spiritual authority which, although universal in nature, was nonetheless exercised within a temporal political sphere (Inglese 2015, p. 76). Machiavelli described it as follows:

It has not been so powerful nor of such virtue as to be able to seize the tyranny of Italy and make itself its ruler; yet, on the other hand, it has not been so weak that, out of fear of losing its temporal possessions, it could not call upon some powerful ally to defend it against whoever might become too powerful in Italy.5

For centuries, the Roman Church had presented the theocratic principle which established that both temporal and spiritual supremacy resided in the hands of the Roman pontiff. In pursuing this political and theological vision, the popes frequently clashed with the imperial power and found support in the Angevin cause, which acquired a Guelf dimension and became a formidable force across the Italian peninsula (Jones 1997, p. 343). What distinguished the Renaissance papacy, however, was that after the Avignon papacy (1309–1376) and the Great Western Schism (1378–1417), the popes’ attention increasingly shifted towards the secular administration of the Papal States, reaffirming their supremacy over the territories that legally belonged to them. This is why scholars agree that, during the Renaissance, one can truly speak of a ‘papal monarchy’ (Richard 1924, pp. 15–40). In fact, throughout the fifteenth century, the papacy became characterised by a process of secularisation which saw fresh territorial consolidation through diplomatic relations established with the strong national monarchies. The papacy’s stronger grip over the temporal domains of the Papal States, along with the necessary sources of economic reserves and authority, came to appear as the most guaranteed security of the libertas Ecclesiae. This was all particularly complex due to the ‘peculiar’ nature which characterised papal power, which had to accommodate a variety of competing political realities. These ranged from the Roman barons to the signori who controlled territories within the Papal States, especially those held mediate subiecte, as well as the governing elites in its subject cities (Prodi 1982, p. 49; Carocci 2010, pp. 84, 93). This is precisely what led the Renaissance historian Jakob Burckhardt to described the Papal States as “a thorough anomaly among the powers of Italy” (Burckhardt 1937, p. 55).

By the time of Alexander VI’s pontificate, the Papal States were subdivided into provinces: the Patrimony of St. Peter, the Duchy of Spoleto, the March of Ancona, the Roman Campagna and Marittima, and the Romagna (Fosi 2025, p. 664). To begin with, most of this territory did not fall under direct papal control, a situation further complicated by the added challenges generated by the Avignon papacy and the Schism. Within the broader context of the proliferation of urban centres of power and emerging tyrannies in the early fourteenth century, the period of the Avignon papacy saw the popes adjust to this new political landscape. This was particularly evident during the legateship of Cardinal Gil de Albornoz, who sought to gain control throughout the papal territories by resorting to the granting of apostolic vicariates in temporalibus (Carocci 2012, p. 84). The region of the Romagna consisted of one such notable example, with the various towns along the Via Emilia ruled by the lords whose rule came to be formally recognised through the granting of auctoritate apostolica. This meant that these signori ruled by formally acknowledging the authority of the pope, who now replaced the commune as the source of legitimate power. Their dependence on papal authority was further reflected in various obligations, such as the payment of an annual census owed to the Camera Apostolica.6 Compared to the rest of the terre Ecclesie, what made the Romagna stand out was that it could be described as the most ‘ecclesiastical’ region of the Papal States, with the papacy having obtained further confirmation of dominium through the formal renunciation of any imperial claims by Rudolf of Habsburg in 1278. The vicariate system thus helped maintain a distinction between legitimate and illegitimate authority amid the coexistence of communal and signorial powers, as well as the papacy’s increasing ‘unfamiliarity’ with its territories during the Avignon Captivity. As a matter of fact, papal endowment of full civic and criminal jurisdiction (merum et mixtum imperium et gladii potestatem) was a legal recognition of that which the lords already held (Larner 1965, p. 90). Although the vicariates were theoretically provisional and revocable, their practical nature changed significantly following the War of Eight Saints (1375–1378). The ties between the vicars and the state became much weaker, leading the vicars to benefit from the military weakness of the popes by continually increasing their political autonomy, and establishing de facto lifetime vicariates. Many even ceased to pay the required censi with impunity, a development that later enabled Alexander VI to invoke non-observance of this obligation as a legal justification for deposing the tiranni (in this case rebelles) of the Romagna7 (Jones 1974, p. 150; Winter 2018, p. 40; Angiolini 2003, p. 154). This evolution ultimately reveals how the balance of power in the Romagna continually shifted according to the relative strength of the lords and the pope.

As illustrated by Peter Partner, a distinctive feature of the ‘Renaissance papal monarchy’ was that it unleashed a strong force which was intent on underlining its territorial sovereignty (Partner 1972). However, a characteristic of the papacy, as opposed to other monarchies, was that as an elective monarchy, each pope had his own interests and convictions, which often resulted in conflicting priorities between a pope and his successor. In line with these broader constraints on papal rule, recent historiography tends to emphasise that, rather than the construction of an ‘absolute state’, the Renaissance papacy had to constantly come to terms with local realities, thus placing greater importance on the notion of ‘compromise’ between the popes and their territorial subjects (Shaw 2025, pp. 78–79). This shows how the consolidation of papal power was a long and tortuous process and, as Ludwig Pastor underlined, upon the election of Julius II (1503–1513), who has been hailed as a ‘founder’ of the Papal States with regard to its territorial sovereignty, “the States of the Church were hardly anything than a name” (Pastor 1898, p. 232). This shows the gradual development of the Renaissance popes’ efforts to consolidate papal authority, the context within which the enterprises of Alexander VI and Cesare must be collocated. It also shows that, despite the gradual nature of the process, by the Quattrocento, the popes had come to recognise that their prestige, autonomy, and spiritual primacy depended on maintaining a stable and well-managed territorial state. Alongside other essential elements, such as self-sufficient finances and effective diplomatic measures, there was, last but not least, the necessity of military strength.

Nevertheless, it is important to emphasise that the ecclesiological reasoning that became characteristic of the Renaissance popes had developed over the course of centuries, reaching its apogee in Boniface VIII’s Unam Sanctam (1302). The evolution of the theological concept of plenitudo potestatis, exercised by the pope as the ‘Vicar of Christ’, affirmed his jurisdictional supremacy in human law, as well as his absolute authority within the universal Church. Such claims, however, met growing resistance from the emerging national monarchies, culminating in the conflict between Boniface VIII and the king of France, Philip IV. This led to the subsequent setback marked by the Schiaffo di Anagni, an insult symbolising the humiliation that eventually contributed to the transfer of the Curia to Avignon (Guillemain 2003). After the end of the Schism, the popes sought to reconstruct, also at an ideological level, the prestige and authority of their vicarage above any form of constitutionalism embodied by the College of Cardinals. This effort became particularly evident in the doctrines developed by the most prominent papal apologist of the fifteenth century, Juan de Torquemada, especially in his Summa de Ecclesia. His arguments again pointed towards the idea of a true ‘papal monarchy’, with the papacy cast in a distinctly monarchical model. Such an arrangement was in fact considered essential for guaranteeing the pope’s authority over the universal Church and for securing the libertas Ecclesiae (Chittolini 2001, pp. 191–217). At the same time, with regard to the Italian political landscape, the return of the popes to Rome coincided with a vigorous strategy to reinforce the temporal domains of the Papal States. This primarily involved reasserting control over the city of Rome and the surrounding region, as well as extending authority over the cities and towns along two key axes: southwards towards Naples and northwards towards the Romagna (Visceglia 2017, p. 83). Guicciardini later explained the situation of the Renaissance papacy as follows:

Abandoning all their [the popes] thoughts to temporal greatness, nor using their spiritual authority, if not as an instrument and ministry of the temporal, they started to appear more secular princes than pontiffs. Their attention and pursuits were no longer the sanctity of life, […] but armies, and wars against other Christians.8

The increasing militarisation of the papacy9 introduced new trends which, as Guicciardini’s judgement suggests, did not develop without stirring controversy. Another illustrative example was presented by the Florentine ambassador Filippo Valori, who observed Alexander VI’s procession towards Santa Maria Maggiore in February 1493. He wrote that this was unprecedented, as the pope was accompanied by “two companies of men-at-arms with long lances, armed as if they were going to fight, something that even in time of war, other pontiffs were never accustomed to do.”10 What appeared most ironic was that the pope was on his way to perform a devotional act. This shows how in the minds of the Renaissance popes, their military aspirations were not perceived as being at odds with the sacred nature of their office or with acts of personal piety. Alexander’s visit to the basilica, despite the presence of a military escort, was in fact a prescribed Lenten statio (De Blaauw 1994, pp. 64–65). A prominent example of how the spiritual and secular domains intertwined was clearly highlighted in the edict of excommunication against the Colonna and Savelli in August 1501, which condemned the barons of the guilt of “perjury and sacrilege”, demonstrating how, for Alexander, there was no distinction between secular and spiritual weapons (Odoricus 1754, vol. 11, p. 365). The correlation between the two spheres is most evident in a correspondence between Alexander and Cardinal Juan Borgia in 1497 when, during a mission in Umbria as apostolic legate, the cardinal spoke of the need for “armed men” [gente d’armi] against the lords, whom he compared to “demons that that do not depart to holy water.”11 This likewise shows how militarisation developed in stages, ultimately culminating in a pope, Julius II, personally leading the papal armed forces in the field. In the case of Alexander VI, the military aspirations of the papacy became concentrated in his son Cesare and, as Machiavelli wrote with regard to the fact that the papacy as a temporal force had now truly became a force to be reckoned with, “Alexander died five years after he had started to draw out the sword [spada].”12

Machiavelli’s reference to the unsheathing of the sword and his use of the expression “through the means [instrumento] of the duke of Valentinois”13 indicates how Cesare was in effect the pope’s manus militaris. In other words, he was the ‘military arm’ of his father the pope who, in turn, aimed to ‘aggrandise’ his son. Given that the Papal States lacked lasting bonds between the pope and his territorial subjects, this brings into the picture the theme of nepotism, which has become synonymous to the Renaissance popes. Although nepotism had negative connotations and was rooted in pietas towards one’s family and ‘carnal attachment’, it nonetheless had significant implications for papal power itself (Carocci 1999). This was because, through such a measure, the popes could maintain control over Rome and the curial offices by relying on trusted troops and officials. In this way, the papacy found centralising initiatives which enabled the pontiffs to tighten their control over the organs of the Papal States and unleash new and stronger forces of military recuperatio. This was especially true because the reconquests of the Papal States presented new opportunities for social advancement. This is not to suggest, however, that this ‘familial policy’ was free of contradictions, particularly its apparent incompatibility with the principle of libertas Ecclesiae (Pellegrini 2010, p. 175). Simultaneous to this, the creation of familial domains legitimised in the traditional vicariate system would have secured the Roman Church’s libertas, especially against intervention from the emerging national monarchies. However, because the Borgia were of Spanish origin, this policy brought about a great sense of alarm in the Roman baronial families who wielded significant influence in their rural strongholds, and which could be described as ‘Roman but not papal’ (Shaw 2009, pp. 101–2, 6). The Roman barons also represented a formidable force of military power owing to their martial traditions. Furthermore, despite, and in several ways, precisely because of their locally rooted power, they were not dependent on papal favour for maintaining their territories. This is because the territory around Rome with its castelli was controlled by these families (the most powerful of which were the generally Guelf-aligned Orsini and the Ghibelline Colonna, among others such as the Savelli and Caetani), who from the thirteenth century had obtained their dominions throughout Lazio not as ecclesiastical fiefs, but as allodial territories (Carocci 2012, p. 83). Their influence extended across a wide network of factional alliances, reaching southwards into the Kingdom of Naples, in which they also held territories, and northwards as far as Umbria (Shaw 2025, p. 79). Owing to the unstable nature of the bonds between pope and barons, their political standing was further accompanied by the absence of any ‘natural’ military duties to the papacy, with the barons serving the pope only when in a state of a settled condotta. The crowning of this paradoxical contradiction was that their military expertise rendered them some of the most coveted condottieri of the period. In this regard, Machiavelli observed that “to frustrate the pope, one needed the Roman barons, who, divided into two factions, the Orsini and the Colonna, […] and always with arms in hand under the pope’s nose, they kept him weak and indecisive.”14

Given such a military situation, some popes, particularly the Borgia popes, who being Spanish were more prone to generate forms of antipathy by more firmly rooted local powers15, started to bestow their nephews or sons the senior command of the papal army. Nevertheless, such nepotism demonstrated that, although such a system rested on a restricted and self-reliant form of power, the lay nephew, particularly in cases involving the investiture of cities, received a governorship that depended entirely on papal favouritism. This, in turn, pointed to the distinctive and somewhat paradoxical features of the papal monarchy. This suggests how the experience of Alexander VI’s pontificate must be seen as the result of a reinvigorated papacy, strong of its economic resources and power, which was able to unleash strong energies of recuperatio, made possible above all through “the occasion of the passage of the French.”16 Despite such factors, as already hinted, the evolution of papal power never developed in a linear way. The appeals to libertas Ecclesiae, made to coincide with libertas Italiae which became the cornerstone of various popes, found an ‘interval’ in Alexander’s ties to France, as his son became Caesar de Francia, even if during the last months of his papacy, Alexander started to speak of the “welfare of Italy.” (Giustinian 1876, vol. 1, p. 243). The foundations of libertas Italiae were laid in 1454, when the Peace of Lodi ended the Wars in Lombardy between Milan and Venice. Pope Nicholas V (1447–1455) subsequently adopted a policy of Italocentrism, sanctioned by the Italic League, which aimed to preserve the political independence of the Italian peninsula from the powers beyond the Alps (Fubini 2009).

The broader context of such a situation was described by Riccardo Fubini as “a conflictual subsystem within the broader system of European powers.” (Fubini 1994, p. 26). Indeed, the popes did not limit themselves to solely reacting to the interventionism of the emerging monarchies, but in them, they also drew inspiration from their secular models of territorial control. A particularly striking example was the reintegratio Hispaniae promoted by the Spanish monarchs, whose efforts at reunification were admired by Italian humanists in the face of Italy’s own political fragmentation (Fernández de Córdova 2009, p. 45). Furthermore, the Hispanic Monarchy had a certain presence in the Italian peninsula through the Trastámara dynasty in Naples. It is thus no coincidence that the first attempts at pacification of the Papal States under Alexander VI counted on the help of the troops of the Catholic Monarchs sent from the Regno. Apart from this, Spanish communities in Rome formed a natio Hispana.17 The development of commercial relations between both peninsulas and the increasing number of offices in the Curia, providing new opportunities in the papal chancery, are some factors that explain the exponential growth of the Spanish community within the city. To make this coincide with the theme of ‘nationhood’ with regard to the Borgia, it is possible to speak of a fracture in the Hispanic community in the wake of the diplomatic crisis of 1498–1499. As will be seen, one of the most evident examples of this was the presence of Spanish troops in Cesare’s army during his campaigns in the Romagna.

Another testimony to the unilinear development of papal attitudes, this time in relation to the ‘familial aspect’, is found in the nepotistic policy. In fact, while Eugenius IV (1431–1447) and Nicholas V had both limited nepotism to the ecclesiastical sphere, a new method of nepotistic policy was introduced by the first of the Borgia popes. The founder of the fortunes of the Borgia in Italy, Callixtus III (1455–1458), inaugurated a new phase of nepotism which has gained the term grande nepotismo, explaining how he could be described as the pioneer of that nepotism which became so characteristic of later Renaissance papacies.18 As opposed to the already existing nepotismo ecclesiastico which, as the term implies, was only limited to the ecclesiastical sphere, the grande nepotismo also extended to include the lay sphere. It essentially aimed at allowing lay nipoti to reach the highest circles of nobility. This was realised by the presence of the ecclesiastical branch in the Sacred College, which in turn safeguarded the fortunes of the lay branch by making use of the resources of the Holy See. This arrangement has been described as a Tempelstaat, for it entailed a convergence of temporal and spiritual authority that produced a new kind of leadership within the Roman Church (Prodi 1982, p. 43). In such circumstances, popes granted their lay relatives the exclusive right to provide military protection for the Holy See, together with a related, and often arbitrary, role in regulating succession (Pellegrini 2010, p. 175). This development illustrated the almost indissoluble connections between papal authority and the networks of consorteria surrounding the papal office, a pattern especially characteristic of the Borgia, Medici, and Farnese pontificates. As Lorenzo de’ Medici made clear in March 1492 when writing to his son Cardinal Giovanni, who later became Leo X (1513–1521), his son was to be “a good ecclesiastic” and devote himself to the interests of the Church. Lorenzo also continued: “It will not be difficult for you to aid the city [città] and our house [casa], for this city is united to the Church, and you must as such be a good chain, as our house is part of the city.”19

In fact, as Peter Partner observed, the first of the Renaissance popes, Martin V (1417–1431), had already demonstrated the effective measures of instrumentum regni, which he held as pontiff and paterfamilias of the Colonna family (Pellegrini 2010, p. 148). Nevertheless, the complexity of this arrangement is evident in the fact that, at Martin’s death, the absence of any real organic links between a pope in power and the fortunes of his lineage exposed the difficulty of maintaining any true ‘continuity’ in the exercise of control over the papal territories. Paradoxically, it was immediately after the death of Martin V that his successor, Eugenius IV, found himself in a weak position precisely because of his hostility towards the Colonna. Eugenius was in fact forced to flee Rome, although he eventually succeeded in restoring the papacy’s temporal power through his links with Florence and the other Italian powers (Shaw 2025, p. 85). This shows how it was within these circumstances that the popes maintained their attitude of underlining papal supremacy both within the spiritual sphere and in the temporal domains of the Papal States. While capitula were normally granted to cities such as Bologna, in cases such as Pope Paul II’s (1464–1471) conflict with the city, the pope was clear that the lords who held territories mediate subiecte should not prosper “under the mantle of St. Peter” (Robertson 2002, p. 18). Returning to the case of Callixtus III, his efforts to strengthen papal power at the expense of the Roman baronial families saw him intervene between the Orsini and the Anguillara in favour of his nephew Pedro Luis, whom he named gonfaloniere of the papal armies (Shaw 2025, p. 87). This antagonism with the Orsini, further fuelled by the pope’s nomination of his nephew as guardian of Castel S. Angelo, then exploded following the death of the pope in 1458, which led Pedro Luis to flee Rome amidst a wave of ‘anti-Catalan’ sentiment. As the case of Pedro Luis demonstrates, the provisional nature of his governorship, as opposed to a vicariate ad vitam, suggests how the lay relative in this case remained essentially an administrator rather than a signore of the territories passed over to him (Pellegrini 2010, p. 178). Thus, rather than an organic link between the pope’s familiares and the state, one can truly speak of a latent friction between the two, ready to reveal itself upon the death of a pope. A noticeable difference in the fortunes of the pope’s family from the time of Callixtus III lies in the career of his other nephew, Rodrigo Borgia (later Alexander VI), who was made cardinal in 1456 and vice-chancellor the following year. In contrast to his brother Pedro Luis, Rodrigo held his office until his election as pope, hinting at the lasting links which an ecclesiastical career could produce, as opposed to the ‘provisional’ nature and politically vulnerable position of the lay nephew.

When Rodrigo became pope in 1492, he aimed at placing Cesare on the same path of an ‘ecclesiastical principality’ which had led him to the tiara (Pellegrini 2010, pp. 231–32). Cesare was in fact granted ecclesiastical benefices from adolescence and, shorty after as his father was elected pope, was promoted to the cardinalate, receiving the administration of the archbishopric of Valencia.20 The Spanish connection was certainly evident when Alexander’s election was met with cries of “Spain, Spain”. The Borgia, after all, spoke Valencian as a first language and among themselves (Sanchis Sivera 1919, p. 35). Nevertheless, this cannot be reduced to the fact that Alexander was merely a ‘Spanish pope’, even if it is true that the only two non-Italian popes elected in the Quattrocento were the Borgia popes. Within the broader context of the papal office and its complex relationship to the theme of ‘nationhood’, the Italianisation of the Sacred College represented an important step in anchoring the papacy firmly within the Italian peninsula after the end of the Schism. This explains why Alexander could declare that “Despite being Spanish by birth […] we are however Italian.” As Marco Pellegrini underlined, the Sacred College did experience a ‘turning point’ under the Spanish Alexander VI; a shift evident through the forty-three cardinals created over the span of eleven years. These included sixteen Spaniards, but it can be argued that this was not a policy of favour towards the Spanish monarchs. Rather, these cardinals formed a ‘Borgia faction’ composed of relatives and clients, and which as was typical of the period, was destined to implode upon the death of Alexander (Pellegrini 2002).

Although all these measures were intended to reinforce the Borgia dynasty itself, Alexander’s promotions also fulfilled a ‘supporting function’, as Wolfgang Reinhard noted. He further emphasised that Alexander’s only true anomaly lay in the elevation of his own illegitimate children (Reinhard 1991, pp. 331–32). Furthermore, the Borgia Spanish heritage provoked forms of antipathy, which further reinforced the ‘suffocating’ control they exercised over the Sacred College. When, to take an example, Alexander conferred upon Cesare the archbishopric of Valencia in 1492, the Ferrarese ambassador, using exaggeration typical of the period, declared that “not even ten papacies would suffice to satisfy all this kinship.”21 However, of the forty-three cardinals created by Alexander, only five were his relatives, fewer than the six relatives promoted by Sixtus IV (1471–1484). Using Marco Pellegrini’s term again, what truly constituted a ‘turning point’ in the case of Alexander was his willingness to accept payments in exchange for red hats; once again a “decisive step towards the Italianisation of the Sacred College.” (Pellegrini 2002, pp. 18–19). As will be seen, beyond the general need for centralisation in a war-torn Italy, this practice formed an important part of Alexander’s search for funds to finance his son’s campaigns. Following the ‘secularisation’ of Cesare, the sale of offices and papal resources were all deployed to sustain his armies, and this is something that may seem most blatant. Nevertheless, as Philip Jones observed, what constituted a paradox in this regard was not the purpose or unscrupulousness of these measures. With hindsight, what distinguished Alexander from his predecessors was that the campaigns financed through such measures actually succeeded (Jones 1960, p. 217). Moreover, coinciding with the decline of conciliarism, as Jennifer DeSilva explained, the diminishing constitutional authority of the cardinals made them increasingly appear as ‘courtiers’ rather than ‘senators’ (DeSilva 2008). This sheds light on the changing nature of the Sacred College, which had in effect become a princely court; a body that prominent families sought to utilise in the formation of ‘dynastic principalities’ and as a means of attaining wealth and influence in civil society. Returning to Lorenzo de’ Medici’s example, his procurement of a cardinal’s hat for his son represented a significant step towards securing Medicean noble status, which, in a Florentine republican context, was attainable only through an ecclesiastical career. In such an atmosphere, especially in a society structured around consorterie, this practice came to be regarded as increasingly ‘legitimate’.22 From this perspective, the supposedly ‘questionable’ moral outlook of churchmen like Alexander was overshadowed by the advantages that the use of illegitimate offspring offered in the creation of dynasties. This, in turn, opened possibilities for advancement in both ecclesiastical and secular principalities, ultimately enabling the ennoblement and the rise in influence and power of the family in question.23

In 1494, two years into the pontificate of Alexander VI, the political history of Italy went through a violent convulsion. When Charles VIII descended into the peninsula at the head of his army, he uncovered the fragility of the political cooperation upon which, until that point, the Italian system of equilibrium had been constructed. The death of Lorenzo de’ Medici in 1492, preceding Alexander’s election by four months, was regarded by contemporaries, particularly Guicciardini, as the start of a new phase of ‘calamities’ in Italy. Nonetheless, Lorenzo’s own political strategy, aimed at expanding his influence in Rome and cultivating an alliance with Naples, had significantly deepened Ludovico Sforza’s sense of isolation, ultimately prompting him to turn to Charles VIII (Mallett and Shaw 2014, p. 11). The effects of such an invasion were described by Guicciardini as follows: “In Italy entered a flame and a plague which not only changed the states, but also the methods of governing them and the methods of wars.”24 The ‘watershed’ in such an important event stood in the fact that, as the same author underlined, from the descent of Charles VIII into the peninsula in September 1494, “other foreign nations and barbarian armies have had the faculty to trample it and devastate it.”25 Guicciardini’s reflection highlights the new ‘opportunities’ that Alexander was able to seize in the wake of the French invasion. However, from the time of the Peace of Lodi, the popes had adhered to a policy of equilibrium that sought to maintain a balance of power among the Italian states and prevent foreign intervention. This was an approach that, in many respects, Alexander continued to uphold during the French invasion of 1494–1495. Alexander joined the Holy League (1495) and was backed by Spain, a decision which as seen was not necessarily owed to any national sympathy but one of pragmatism (Fernández de Córdova 2005). An understanding had also been reached with Naples which went hand in hand with new negotiations with Spain, signalled by the papal bull Inter Caetera (1493). This was again demonstrated in Alexander’s decision to build a power base in Spain for his other son26 Juan (the duke of Gandía). However, Juan’s return to Rome in 1496 suggested that Alexander’s intention was that of putting in second place his status as a Spanish nobleman and instead installing him in Rome as the most important Roman baron. This overt ‘interference’ in the Roman campagna at the expense of such a long-rooted family as the Orsini might help explain the mysterious murder of the pope’s son on 14 June 1497.27

The overall situation indicates that the fortunes of the Borgia family, together with the new French presence in Italy, opened possibilities for new forms of advancement that suited the ambitions of both the dynasty and the Papal States. From this point onward, even though Cesare’s secular aspirations were well known, regardless of his possible involvement in his brother’s murder, his path towards a ‘secular principality’ became clearly established (Pellegrini 2005). As Marco Pellegrini has emphasised, this moment marked the transition from an ‘ecclesiastical principality’, flexible and inherently dependent on the provisional nature of papal patronage (though more secure when the pope died before such a transition could undermine it), to a ‘secular principality’. This would have allowed Cesare to construct a political power base capable of outlasting the pope and enabled him to rely on his own material resources (Pellegrini 2005). Nevertheless, an analysis of the development of Cesare’s secular career will illuminate the identity of such a principality, and the effects of the autonomy it permitted.

3. Caesar de Francia

At the outset, it is appropriate to interrogate what this ‘secular principality’ actually aspired to achieve, particularly in relation to the ‘territorial outlook’ of the Borgia papacy within the Italian peninsula. Previous historiography tended to propose a ‘dynastic aspiration’ intrinsically tied to plans for the establishment of an ‘Italic Kingdom’. Other propositions included aspirations which foresaw the direct rule of the papacy over its territories, while preventing “the foreigners from becoming masters of all Italy” (Sacerdote 1950, pp. 338, 815; Soranzo 1960, pp. 344–45). The following pages, however, argue that Cesare’s ‘place’ in Italy was shaped above all by the Italian political landscape, which offered real and immediate opportunities. In fact, it is worth recalling that the previous Borgia policy under Callixtus III had looked towards Naples (and thus outside the Papal States) in the pope’s desire to replace Alfonso of Aragon with his nephew Pedro Luis, even if this never materialised. More concretely, Sixtus IV had favoured his dynasty by installing his nephew Girolamo Riario in the Romagna. In fact, the evolution of interstate relations among the five major Italian powers had fostered an ‘Italian-oriented’ balance of power. Although this witnessed a more firm temporal situation for the papacy, it ensured that the peninsula continued to be a theatre of alliances, patronage, and connections with other powers (Shaw 2025, p. 85). In fact, the various interests behind the ambitions of Sixtus IV, which led to the Pazzi Conspiracy (1478) and the war that followed, had greatly perturbed the quiete d’Italia between the Peace of Lodi and the Italian Wars. Alexander VI’s pontificate, therefore, cannot be regarded merely as an anomaly. It was, rather, a response to the challenges posed by the politics of the time, an effort to assert the authority of Rome in continuity with the direction set by earlier popes, within the emerging system of Italian and European states. Parallel to this, the nepotistic policy reveals the complexity of the relationship between papal authority and the organs of state. This is because the very dynasty established in the Romagna by Sixtus IV was displaced by another papal creation, in this case, Cesare, demonstrating once again that, despite the absence of any explicit dynastic blueprint for the region, the Romagna had become a central target of papal secular ambitions.28

It is only against this backdrop that one can speak of Alexander VI’s pontificate going through a ‘diplomatic revolution’. This is because the negotiations which followed were not obvious from the start, and Alexaner’s initial ties to Naples earned him some territorial concessions within the Regno. It also reflected a consistent policy aligned with the papacy’s traditional policy of maintaining the kingdom as feudally subordinate. This approach also sought to preserve a vertical Milan-Rome-Naples axis, and thus an Italian alliance which would have prevented interference by external powers. 1498 had seen the sudden death of Charles VIII, who was succeeded by his cousin the duke of Orléans. The Orléans had inherited claims on Milan through Valentina Visconti, a dynastic inheritance which was mobilised to legitimise French intervention in the Italian peninsula. In fact, as David Abulafia underlined, it was mostly with the ascent to the throne of Louis XII that the political composition of Italy was definitely transformed (Abulafia 1997, p. 255). In fact, upon the coronation of the new French king, the Venetians, who had territorial ambitions in Lombardy, immediately informed him that they were ready to come to an arrangement if he desired an alliance (Setton 1976, vol. 2, p. 509). This wider context is important to understand Cesare’s place as the instrument of his father’s policies. As already explained, it shows that it was not obvious that Cesare’s attention ended up looking north towards the Romagna. However, the complexity of the situation lies in the fact that, as seen, among all the terre Ecclesie, the Romagna had become one of the most important arenas of intense negotiation and conflict. It was there that vigorous efforts to advance the papacy’s dominium were carried out, in constant negotiation with the existing local powers (Angiolini 2003, p. 152). At the same time, all this was in line with Alexander’s policy of ‘settling’ his son in the lay sphere, especially due to the fact that the transition from a ‘cardinal prince’ to a ‘lay prince’ was not without difficulties, with Cesare’s ecclesiastical revenue amounting to 36,000 ducats annually (Creighton 1897, vol. 4, p. 304).

As Machiavelli reported, already “at the end of October of 1497”, the pope had approached Charles VIII for assistance in finding a bride and a settlement for his son (Machiavelli 1858b, p. 216). By 1498, the pope’s interests remained focused on Naples. Cesare’s position, however, created difficulties when attempts were made to arrange his marriage to King Federigo’s daughter, Carlotta of Aragon. Although pressure from the duke of Milan had facilitated the marriage between Lucrezia Borgia and the duke of Bisceglie, Federigo continued to resist the prospect of giving his daughter to Cesare. His opposition was supported by Spain, both courts declaring that the secular career of a former cardinal constituted a scandal, and declaring that “as Catholics, they opposed this deposition”.29 In fact, the situation became increasingly entangled with the relationship between Alexander VI and Spain, for the Spanish monarchs viewed such a move within the Regno, which fell under their protection, with deep suspicion. Their relations with the pope had further deteriorated over the possessions of the legitimate heir of the duke of Gandía in Spain (Fernández de Córdova 2009, pp. 36–38). With the pope now intent on establishing a firm foundation for the lay branch of his dynasty, he had failed to secure control over the fortunes of the deceased duke of Gandía. In light of this setback, and upon learning of a Spanish–Neapolitan front, Alexander announced that “he would bring back the king of France.” (Quoted in Vega 1842, p. 6).

Cesare’s search for a bride thus prompted a papal shift towards the north, since Carlotta was living at the French court. As Louis XII signalled his willingness to collaborate with Alexander, driven by his own need to secure a divorce from Joan of Valois, in order to marry Anne of Brittany and obtain the duchy, the papacy and France entered into a series of negotiations that laid the groundwork for Cesare’s fortunes in Italy.30 French claims on Milan, ‘the key to Italy’, and Naples, convinced Alexander that, with a strong French presence both to the north and south of the Papal States, the king of France was the best candidate to secure the lands which he wanted to bestow upon Cesare against any threat posed by a future pope. With Louis thus adhering to Alexander’s requirements for a settlement to his son, the king also “promised and swore in front of God and the Virgin Mary to defend, guard, and protect his said Holiness both temporarily and spiritually.”31

Cesare’s return to the secular sphere was granted on 17 August 1498, when he appeared before the consistory and “declared that from his early age he had been inclined in spirit towards the secular condition”.32 As Sanudo recorded, Cesare “was given permission to put down the hat, and make himself a soldier and marry.”33 On the same day of Cesare’s resignation from the cardinalate, the French king’s envoy Louis de Villeneuve arrived “to conduct the reverend lord of Valencia into the Kingdom of France”.34 Cesare departed for France in October, where he was received by Louis XII at Chinon, while negotiations continued between both sides (Burchard 1884, vol. 2, pp. 495–96). Alexander’s policy now pointed to how he had truly seized the opportunities created by the ‘watershed’ inaugurated by the French invasion. In fact, alarm from Italy erupted over the new negotiations with France and “in the consistory, Cardinal Ascanio Sforza told the pope that by sending his son to France, he wanted to bring about the ruin of Italy and the pope responded that it was his brother who had brought the French in Italy.”35 This exchange illustrates that Alexander was indeed responding to the political circumstances that had unfolded, although naturally tied to the project of promoting his son. To realise this, he seized the return of French arms to Italy, called into the peninsula, as Guicciardini then stated, “by our own princes”.36 As negotiations progressed, Louis received the annulment of his marriage, the king’s minister Georges d’Amboise was given a cardinal’s hat, and Cesare became officially invested with the county of Valentinois (elevated to a duchy) and Dois.37 Cesare’s ties to France were thus sealed through his duchy, which provided him with an annual income of 20,000 francs and stipends for a hundred lances (Pélissier 1895, p. 337; Guicciardini 1971, p. 352). In an almost emblematic coincidence, this marked Cesare’s ‘transformation’ from ‘cardinal of Valencia’ to ‘duke of Valentinois’: an alter Caesar who, having emerged from the spiritual sphere of the Roman Church, now embodied its military dimension.

The diplomatic importance of both France and Venice in Cesare’s place in Italy is evident in the fact that, while negotiations over the marriage agreement were still underway, the two states agreed to an alliance at Blois in February 1499. With Carlotta continuing to refuse marriage to Cesare, despite the influence of the French king, the splendid reception Cesare received in France could not conceal the uncertainty surrounding the negotiations, even if he had already secured his duchy. The pope himself grew increasingly anxious, at one point declaring that “if he did not have his son in France, he would ally himself with Milan.”38 The marriage project with the House of Trastámara was ultimately abandoned and King Louis finally committed himself to proposing a new bride for Cesare. This was Charlotte d’Albret, sister of the king consort of Navarre, John III, and a relative of Louis. The contract was settled and the marriage celebrated at Blois on 10 May 1499 (Burchard 1884, vol. 2, p. 532). The implications were that Navarre formed a contested frontier between Aragon-Castile and France, a theatre of conflict between two powers whose ambitions also extended to the Italian peninsula, and one in which Cesare was to become a protagonist (Cariñanos 2007, pp. 25–26). Moreover, the marriage between the House of Navarre and the pope’s son complemented the growing network of pacts between Rome and France, while simultaneously strengthening the ties between France and Navarre (Boissonade 1956, p. 11). It was the marriage agreement, rather than an official alliance, which bound Alexander, now visibly “all French” (Sanudo 1879a, vol. 2, p. 826), and the French king, with the pope now convinced that he could “give some place in Italy to his son.”39 The joyful reception in Rome of the news that Cesare had consummated the marriage “eight times”40, underlining the canonical solidity of the union, sheds light on the central role of the marriage in cementing Franco–papal cooperation. It was precisely upon the conclusion of the marriage contract that the Treaty of Blois, signed three months earlier, began to take full effect; in exchange for papal neutrality before the invasion of Milan, the pope would obtain military support to restore his control over the Romagna. This shows how it was precisely at this moment that Alexander had totally matured the prospect of installing his son in the Romagna. The intention is made particularly clear in the wording employed during Cardinal Juan Borgia Lanzol’s mission to Venice in September 1499, which stated:

The pope intends with the favour of the king [of France] to restore [ricuperare] to the Church some territories of the Romagna and as such asks the Signoria to abstain from any aid or protection to the vicars.41

The diplomatic undertakings and the weight of French military power thus indicate how Cesare’s conquests can truly be described as a ‘policy of pacts’ with the Kingdom of France and the Republic of Venice. Cesare was now invested as lieutenant general of the French king and accompanied Louis during his triumphal entrance into Milan in October 1499, following its rapid conquest. He then proceeded to initiate the conquest of his first targets, Imola and Forlì, held by Caterina Sforza as regent for her son Ottaviano Riario. The help which Caterina had sent to Ludovico was sufficient for the king to favour Cesare’s impresa, and from the new French acquisition of Milan, the king also loaned Cesare 45,000 ducats for the enterprise. He received the sum “in the name of the Roman Church.”42 It was precisely upon the taking of Milan that Alexander used the grounds of non-payment of the annual census of the vicars as legal grounds for their deposition. With the lords now declared rebelles, this provided the formal justification for Cesare’s first impresa.43 Before the start of his campaign, Cesare received 300 lances françaises under the command of Yves d’Alegre and 4000 Gascons and Swiss under the command of the Bali of Digione, paid by the pope.44 Louis also wrote to Giovanni Bentivoglio, signore of Bologna, ordering that Cesare’s army receive assistance and passage in the following words:

In compliance with the request of our Holy Father the pope, we want, as protector of the Church and the Holy Apostolic See, to help him to recover his lands and domains of Imola and Forlì, which as is clear to us, are domains of the said Church.45

Just as French aid and authorisation were necessary for Cesare’s campaign to commence, Venetian approval was likewise necessary. This was because the Venetian Republic was equally interested and highly influential in the regions which overlooked the Adriatic. As the Venetian ambassador Girolamo Donato had once declared to Alexander: “Show me Your Holiness, the donation of the Patrimony of St. Peter, and on the back there is the concession of the Adriatic Sea to the Venetians.”46 This again illustrates that papal diplomacy had to constantly seek the non-belligerence of Venice, the true protagonist of the Romagnol political chessboard ever since its conquest of Ravenna in 1441. In fact, up to this point, Venice still refused to withdraw its protection over Faenza and Rimini, stating that “it cannot permit that the pope acquires, but regarding the other cities it will not move any interdiction”.47 Only with these agreements reached, with the diplomatic sphere paving the way to military action, could Cesare initiate his conquests against the Sforzeschi with the backing of his father, in turn writing to the Marquis of Mantua Francesco Gonzaga and asking him “to gather as much gunpowder as possible for the expedition undertaken at Imola.”48 The campaign against the former Riario vicariate was in fact a purely papal military operation, and it was Cardinal Juan Borgia Lanzol, as papal legate, who received the formal obedience of the citizens of Imola (Mallett 1987, p. 180). Imola and Forlì were conquered between November 1499 and January 1500, and Cesare also planned to seize the other Sforza lordship of Pesaro. However, the campaign was cut short when his French troops were summoned back north due to Ludovico’s brief return to Milan (Mallett and Shaw 2014, p. 57). This episode clearly demonstrated Cesare’s dependence on France, particularly with respect to his military ambitions. As noted, the close relationship between Cesare and Louis had been formalised through his appointment as regius generalis locumtenens. This was a title which certainly offered a high degree of protection. However, it was also a conditioning factor which brought about obligations owed to his sovereign. Caesar de Francia, after all, remained Cesare’s preferred signature.49

Cesare returned to Rome in February 1500 and was made gonfaloniere and commander of the papal armies on 29 March at the Basilica of St. Peter (Burchard 1885, vol. 3, p. 26). This is an important detail because, when Cesare swore fealty to Alexander, he pledged to “conserve, defend, increase and promote the rights, honours, privileges and authority of the Roman Church, Yours [of Alexander] and of Your successors.”50 This shows how it was Alexander in his capacity as pope who declared to his son:

Receive the insignia of the preeminent office of Standard-Bearer [Confaloneriatus], placed upon your head for us in the name of the Father, and of the Son, and of the Holy Spirit; and understand that henceforth you are bound to the defence of the faith and of the Holy Church.51

The ‘familial sentiment’ was nevertheless conspicuous in Alexander’s reaction upon Cesare’s return to Rome, as he was so overjoyed that he “laughed and cried at the same time.”52

The theme of familial attachment can in turn be made to coincide with the subject of ‘nationhood’. Although the Borgia were now closely connected to France, Cesare’s army gradually became composed of an increasing number of Italian and Spanish captains. These included the Romagnol Dionigi di Naldo and the Spaniards Ramirez de Lorqua, Ugo de Cardona, and his trusted and devoted Micheletto Corella (Larner 1966, p. 259). This list revealed the fusion of Spanish and Italian characteristics embodied by the Borgia, whose distinctly ‘Hispanic’ identity remained especially noticeable in cultural tastes considered ‘foreign’ in Rome. This was particularly the case in bullfighting, a sport in which Cesare excelled. On one such occasion, “he killed seven bulls”, decapitating one in a single strike, an exploit which “appeared great in front of all Rome” (Sanudo 1880, vol. 3, p. 846). The Catholic Monarchs were aware that the true guarantor of Cesare’s power in Italy was Louis XII, although they would still consider the advice of Cardinal López, who in early 1500 wrote that Cesare, “tired of the French, will be a good Aragonese [...] with the hope that your Highnesses will grant him favours.”53 All this, ranging from questions of nationhood to manifestations of familial sentiment, illustrates the blurred line that held together ‘familial aggrandisement’ and the secular interests of the Papal States. Again, one must understand that the ‘policy of pacts’ used to explain Cesare’s ability to launch his campaigns also came to include his territorial possessions, particularly when it came to coming to terms with his conquests. In fact, Cesare did not impose himself on the local populations, aiming instead to seek papal legitimacy through the vicariate system and thus as a feudatory of the Roman Church (Angiolini 2003). It is in fact necessary to underline that Cesare always held the cities of the Romagna Pro Sancta Romana Ecclesia, with his reforms aimed at creating a more unified territorial state, not in a stately manner, but a signorial one under his vicarial control. The legal value of such a position can be noticed from the start, in the pope’s decision to invest his son with the vicariates of Imola and Forlì.54

The importance of Venetian approval in Cesare’s conquests can be further reconstructed when it came to his second impresa. New opportunities arose when the Jubilee of 1500 enabled the pope to proclaim a crusade at a time when the Venetian Republic’s resources were severely strained by its conflict with the Turks. With papal diplomacy pressing on the forfeiture of Venetian protection over the vicars, the Signoria finally complied in September, and declared that it was ready to “embrace the duke of Valentinois and hold him as a good son and give him money and convenient conditions.”55 Nevertheless, the uneasy nature of the relationship is evident in Venice’s refusal to bestow upon Cesare the title of captain, stating that he had attacked those lords which had previously fallen under its protection (Alvisi 1878, p. 123). Furthermore, before formally withdrawing its protection over Faenza, the Serenissima attempted to compel Astorre III Manfredi to pay the census, an effort clearly aimed at Venice’s attempt to retain its lines of communication between Faenza and Venetian-held Ravenna (Angiolini 2003, pp. 154–55).

Sanudo provides an illuminating portrayal of the conflicting interests at play during the negotiations surrounding the proposed crusade. While the pope told one of the Venetian ambassadors that he “wished to die for the faith”56, the ambassador reported that it seemed “like the pope only has at heart the enterprise of the Romagna.”57 Indeed, Alexander once again made his priorities explicit by guaranteeing revenues for the Romagnol campaign. Sanudo notes this in connection with the creation of cardinals in September 1500: “He [Alexnader] sent […] and the duke of Valentinois, who rode to the most reverend cardinals, asking them to be content of making new cardinals in so much as he can have money for the enterprise of the Romagna.”58 These details are important, for they demonstrate how papal resources and diplomacy, whether related to the crusading initiative or to the sale of offices, were fully mobilised to meet Cesare’s campaign. Regarding France, Louis XII again looked favourably upon the Borgia enterprise in the Romagna and, as Machiavelli observed, Louis “held the pontiff in high esteem, more than any other Italian ruler.”59 Machiavelli, however, also recognised that the French king granted the pope’s requests not out of any genuine desire to promote Cesare’s aggrandisement, but because he was unable to restrain Alexander’s demands (Machiavelli 1875a, vol. 1, pp. 193–96). In fact, although Louis allowed for the creation of a Borgia state, he desired that Cesare did not extend his ambitions beyond the Romagna. Following the conquest of Pesaro and Rimini, he wrote a letter to the bishop of Luçon, Pierre de Sacierges, his lieutenant in Milan, expressing satisfaction at his “cousin’s” victories, but stressing that he remained obliged to defend his allies and confederates, by force if necessary, should any of them be threatened (Nitti 1876, vol. 1, pp. 104–5).

A case study illustrating the interplay of the various spheres of influence emerges clearly during the Siege of Faenza and its aftermath, especially in light of the resistance which Cesare’s army encountered. In fact, Alexander increased his diplomatic efforts, which intensified once he learned of the unfavourable progress of the siege, soon celebrated as an instance of heroic resistance (Guicciardini 1971, pp. 436–39; Alberti 2006, p. 133). The pope protested to King Louis that both the Florentines and the Bolognese had furnished assistance to Astorre Manfredi, given that both Florence and Giovanni Bentivoglio fell under the king’s protection. Ties between the Manfredi and the Bentivoglio, combined with Florentine interests in the area, reveal the dense and overlapping network of regional alliances, as had been seen in the time of Sixtus IV. However, coinciding with the start of the siege was the agreement between Louis and Ferdinand of Aragon concerning the partition of the Kingdom of Naples in the Treaty of Chambord-Granada (October–November 1500) (Mallett and Shaw 2014, p. 58). The pope’s approval of the division of Naples meant that Louis again required the pope’s favour. From France, Machiavelli reported that Louis had told him that “should the duke of Valentinois attempt anything against the Florentines or Bologna, we shall immediately take action and, without delay, proceed against the said duke.”60 At the same time, the king dispatched his orator to Bentivoglio, instructing him to cease aiding Faenza and reach an agreement. This reveals that developments in Naples gave Louis some leverage over Bentivoglio and helps explain the various ‘pacts’ Cesare had to confront.

With the surrender of Faenza in April 1501, Cesare turned his sights on Bologna and occupied castles within Bolognese territory. His immediate objective was to seize Castel Bolognese, situated between Imola and Faenza, thereby securing a continuous territorial corridor linking his recent conquests. This advance caused significant alarm within Bologna, where Giovanni Bentivoglio attempted to organise resistance, with the population arming itself “to liberate the patria from the hands of priests and marani.”61 As had occurred earlier when Bentivoglio refused to allow Cesare’s troops to winter in Bolognese castles during the Siege of Faenza, the city sought to defend its autonomy by appealing to the capitula previously granted by earlier popes (Alberti 2006, p. 133). In face of this resistance, Cesare could invoke a higher source of legitimacy, that of his gonfaloniership, as he insisted:

I see that you Bolognesi are of such a nature, that not wanting to recognise your superiors, I protest to you that not wanting to give me Castel Bolognese, through disobedience, you are deprived of any capitula which you have with the pope.62

The shows how, although the Bolognesi could state that Cesare’s demands amounted to nothing but blackmail [frode] (Alberti 2006, p. 133), his requests nonetheless possessed legitimacy insofar as he had been entrusted with a special commission by the pope himself. Standing between Cesare and Bologna, however, were his own men: Cesare’s Guelf condottieri now found themselves in a delicate situation. Giovanni Bentivoglio was one of their long-standing allies. Before the situation could escalate, an agreement was reached and the reggimento of Bologna agreed to surrender Castel Bolognese and concede a stipend of three years for one hundred lances. Thus, in spite of any claims of legitimacy, Cesare set his sights on Bologna, irrespective of his captains’ reluctance. This revealed that, despite their close association, he had no intention of adapting his schemes to the interests of the Guelf faction. This helps explain why the terms ‘Guelf’ and ‘Ghibelline’ remained powerful enough for the papacy to use them to shape political action and maintain equilibrium. (Casanova 1981). Nevertheless, even if they remained useful terms, the agreement which Paolo Orsini reached with Bentivoglio on Cesare’s behalf hints to how the Guelfs in his army had exerted significant influence in persuading him to reach terms (Shaw 1981, p. 13).

The presence of Orsini condottieri in Cesare’s army is particularly significant. Once Alexander VI turned to the French, his attitude towards the Orsini also changed and some younger Orsini, such as Paolo and Francesco, were given condotte in the army recruited by the pope for his son (Shaw 1981, p. 11; 2015, p. 236). Sanudo makes it clear that when the pope received the Venetian envoy concerning French affairs, Cardinal Orsini was constantly present (Sanudo 1879a, pp. 113, 140, 250, 344). This shows how the Orsini’s longstanding ties to France, once a major obstruction, turned into a valuable diplomatic asset in Alexander’s efforts to secure cooperation from Louis XII. It is still worth noting that this outlived its usefulness and, instead, become a serious hinderance in the last months of Alexander’s pontificate. However, from the start of Cesare’s campaigns in 1499 until 1502, the close association between the Borgia and the Orsini can be noticed in the considerable importance of the Orsini condottieri in the papal army. In fact, since Cesare spent a total of ninety-five days with his army over the course of his imprese, much of the operational responsibility and military planning fell to the Orsini (Shaw 1981, p. 11). This did not mean that the whole dynasty was aligned with the pope. To take a prominent example, Giangiordano Orsini, lord of Bracciano, who had accompanied Cesare to France, refused condotte in the papal army, preferring to remain in French service. The same went for Niccolò Orsini of Pitigliano, who was serving as Venetian captain-general. When the news reached Rome that Ludovico Sforza had been defeated at the Battle of Novara (April 1500), the news was greeted with cries of “Urso” [Orsini] and “Francia” (Burchard 1885, vol. 3, p. 35). In line with this, Cesare had to come to terms with the inclinations of his condottieri, especially the Guelfs in his army, who wanted to exact vengeance against the Ghibellines in the name of the papacy. This was most clearly visible in Cesena, the one city of the Romagna already under direct papal governance (immediate subiecta), even if the city was characterised by violent conflict between the Tiberti and Martinelli families. On 26 July 1500, armed Guelfs ran through the streets with a standard depicting a red cross and shouting “Chiesa, Chiesa.” Then, on 2 August, Polidoro Tiberti rode through the crowd and stirred it to proclaim Cesare as lord (Alvisi 1878, pp. 117–18). Following these events, Alexander conferred upon Cesare the lordship of Cesena, and when Cesare reunited the leaders of the city’s factions, he managed “to reconcile and pacify them, so that, with other matters in the city settled, they may be able to live together in harmony.”63

From the case of Cesena, which served as a sort of ‘capital’ of Cesare’s domains, a similar accommodation with his condottieri occurred in Tuscany, a region which entered Cesare’s designs after his second impresa. This was particularly so because the Orsini captains in his service supported the Medici, to whom they were connected, whereas Vitellozzo Vitelli wanted to strike against Florence in order to avenge the death of his brother at the hands of the Republic (Guicciardini 1971, p. 445). Thus, between May and June 1501, Cesare returned to Rome by way of Tuscany. Along the way he laid siege to Piombino, whose ruler, Jacopo IV Appiano, had not secured Louis XII’s protection, and also threatened the Florentines. He undertook this despite having received explicit instructions from his father to return to Rome immediately. This was one of the first examples involving Tuscany which demonstrated that Cesare’s and Alexander’s objectives could come into conflict. By this point, having conquered the major cities of the Romagna, Cesare was already showing interest in the former subject cities of Florence, which had freed themselves from the dominante. The incorporation of these cities, along with a part of Florentine territory, would have allowed Cesare to assume the title of King of Tuscany (Pellegrini 2010, p. 237). However, Louis preferred to continue serving as the protector of Florence in exchange for generous monetary payments, which he accepted in return for curbing further Borgia expansion (Pellegrini 2009, p. 97). The king’s vetoes thus suggested how territories that could be added to Cesare’s domains all depended on diplomatic possibilities, whereas the Borgia alliance with France implied that Alexander could still direct his attention to matters which brought advantage to the temporal cause of the papacy.

4. Between France and the Papacy

Cesare’s rule in the various cities of the Romagna, always grounded on papal legitimacy, became more territorially ‘coherent’ when the first reference to him as ‘lord of the Romagna’ appeared in early May 1501.64 By the second half of May, this was sanctioned with the creation of the Duchy of the Romagna: “His Holiness the pope has sent to his son the duke of Valentinois the title of duke of the Romagna, with hat and sword and he has also sent him the rose of this year.”65 This demonstrated Cesare’s position as both a duke in his own right and his dependence on his father, who bestowed the dukedom “with the approval of the consistory.”66 In fact, during the conflict in Naples, Alexander insisted that Cesare turn his attention to matters which were more in line with his duties as the agent of the papacy. He therefore ordered him to strike against the Colonna, whose renewed ties to Naples secured their condemnation. This development was only possible because the Colonna were in the service of the Trastámara dynasty, whom they had temporarily abandoned during Charles VIII’s descent in 1494. In fact, they had aligned with France in exchange for the restoration of their Neapolitan fiefs, and Charles’s entry into Rome was met with cries of “Francia” and “Colonna” (Burchard 1884, vol. 2, p. 217). Nevertheless, the Colonna returned to the service of Naples, and the ‘private war’ between the Orsini and the Colonna over Tagliacozzo was concluded with the Peace of Tivoli in 1498 (Visceglia 2017, p. 93). The enemies of the Borgia were satisfied that such a united front could “strike down the Bull, plunging its calves into the water of the Tiber.”67 However, as seen, the condotte the Orsini were granted in the papal army represented a continuation of their traditional Guelf alignment. In fact, in the summer of 1501, the Orsini took over Tagliacozzo and other territories which the Colonna had received from Federigo of Naples, while Cesare played a pivotal role in the ferocious Siege of Capua (July 1501) as lieutenant of the French king (D’Auton 1891, vol. 2, pp. 42–47; Burchard 1885, vol. 3, p. 152).

Upon Cesare’s return to Rome, the pope issued a bull depriving the Colonna and the Savelli of their fiefs and ordering the confiscation of their already occupied territories (Mallett 1987, p. 189). Nevertheless, such an obvious victory was still not a definitive one. This was because the deeply rooted local traditions of the baronial families constituted a very strong force. In fact, rather than fighting to the bitter end, the Colonna, headed by Fabrizio Colonna and his kinsmen, deemed it wiser to surrender their territories to the pope, rather than see their estates ravaged by the French. They knew that the fortunes of the pope’s family could be swiftly reversed upon the death of the reigning pontiff, enabling them to reclaim their lands (Shaw 2015, p. 230). Similarly, the grounded nature of their power meant that they could survive and adapt even if their most important territories, such as Rocca di Papa, had been taken from them (Petrucci 1982). Their ‘rooted longevity’ stood in stark contrast to Cesare’s far more volatile political position.

At the same time, the brutality which characterised the Siege of Capua sheds light on how the French in Italy were not only feared for their new methods of warfare, but above all for the ‘brutalization’ which accompanied it (Fournel 2024). As Leandro Alberti reported with regard to the French army’s passage through Bologna, the French acted “like barbarians and insolent and unbridled men.”68 This shows how Cesare had to come to terms with this furia franzese, especially when it affected his own territories, as was vividly demonstrated during the conquest of Forlì. The sack was so devastating that Andrea Bernardi described it as “similar to the pains of hell.”69 These circumstances might help explain Cesare’s gradual distancing from French troops, particularly the notorious Gascon stranieri, who were largely responsible for the disorder and destruction that followed. In fact, in November 1502, Machiavelli noticed how Cesare had initiated a gradual transition from “French arms” to “his own.”70 When speaking of ‘local arms’ in Cesare’s army, however, one must recall that the ‘local’ Romagnoli were renowned condottieri long before Cesare’s arrival. This means that the 800 infantrymen witnessed by Machiavelli were actually mercenaries under the command of the condottiere Dionigi di Naldo (Larner 1966, p. 258). This shows how Cesare’s army continued to be a ‘mercenary army’.

At the same time, Cesare’s reduced reliance on French troops fits well within the broader framework of his policy of ‘pacification’ throughout his territories. His authority became less dependent on the brutal methods associated with some of his Spanish commanders. The most striking example was of Ramírez de Lorqua, initially invested with “full power” in Cesare’s stead, until his dramatic execution signalled a shift towards a form of rule grounded more in administrative measures and the appointment of respected and trusted native officials (Machiavelli 1961, p. 25; Mallett 1987, pp. 222–23). This was recognised by theorists such as Machiavelli as an example of buon governo in the lawless Romagna, where “no republic or vivere politico” could emerge.71 It is true that the region continued to be one of disorder long after the breakdown of Borgia government, and Guicciardini described it as a land “where there are many wounds and several new and old injuries, where men are commonly dishonest, evil, and do not know honour.”72 This shows how Cesare’s ‘good government’ was an anomaly in a region which had long been accustomed to the collapse of civil government (Larner 1972). Despite the vicarious nature of the government, it nonetheless witnessed centralising initiatives such as the establishment of a Rota all’uso di Roma, as well as the creation of tax-collection and military-recruitment systems that encouraged self-sufficient fiscal and military resources. These projects, however, did not have the time to develop to the full, both because of Cesare’s constant military dependence on mercenaries, as well as his continuous financial reliance on the Camera Apostolica and its associated Sienese bankers, notably the Spannocchi and Chigi families (Ait 2003, p. 63). To give one concrete example, between May and June 1502, the Camera Apostolica paid the sum of around 3300 ducats for gunpowder alone.73 It is true that the Borgia experience can be placed within the broader context of the discontinuous nature of rule in cities such as Forlì, which had seen the successive governments of the Ordelaffi, Visconti, Riarii, and then the Borgia. Nevertheless, the Borgia experience, despite its rapid collapse, signalled visibly shifting patterns of power. Therefore, the legacy of the Borgia to the future of papal Romagna lay precisely in the almost complete disruption of the Romagnol noble forces without causing irreparable breaks in the balance of the city elites (Casanova 1981, p. 55). This is clearly reflected in the capitula granted to Faenza upon its surrender on 25 April 1501. These not only maintained the statutes of the city, but also preserved the patrimonial and jurisdictional privileges of its ruling class over the contado, from safeguarding movable and immovable property of the Faentini in the Val di Lamone, to the reservation of “offices of the city of Faenza and its domain [...] to the men of the said city.”74 (Angiolini 2003, p. 158)

The interdependence between Cesare’s standing as duke of the Romagna and gonfaloniere of the Roman Church can again be observed in his third impresa, in the summer of 1502. The political situation permitted him to look to the territories of Urbino and Camerino to the south. This coincided with a moment when to the north, Venice was still militarily preoccupied, while the marriage between Lucrezia Borgia and the heir of Ferrara, Alfonso d’Este, represented the pinnacle of Borgia ‘pontifical’ and ‘familial’ policies which came to coincide with the interests of Cesare’s duchy. In fact, marriage into the House of Este secured considerable coverage in the northeastern area of the Romagna, which Venice would not yet have tolerated being directly controlled by the popes, or by those acting on their behalf (Angiolini 2003, p. 173). This again raises the question of a Borgia dynastic legacy, with Cesare well aware that his own exploits were tied to the physical presence of Alexander VI. As Giustinian reported in June 1502, the pope “was in some difficulty with the duke, who wants another 20,000 ducats […] and although the pope reckons that it would be difficult to give him these money, he will comply with the wish of the duke in this, as he does in all other things, and he will find the money, wherever he wishes.”75 Such a ‘divergence’ between Cesare and Alexander might also be implied when, upon seizing Urbino (Burchard 1885, vol. 3, p. 209), Cesare wrote to the pope, excusing himself “if he had done this enterprise without the awareness of His Holiness.”76 As Cesare mentioned that Guidobaldo da Montefeltro, duke of Urbino, was helping Giulio Cesare Varano, lord of Camerino, Alexander had already hinted that he was aware that “the neighbouring lords” were aiding Camerino (Giustinian 1876, vol. 1, p. 30), showing how he must have been expecting the news, and leaving it plausible that Cesare and the pope had discussed the matter beforehand. This shows how the cooperation between the two could still operate effectively, and that it had not yet exceeded its limitations.

Although the taking of Urbino was met with jubilant celebrations in Rome, and it could be described as Cesare’s greatest coup to date, it nonetheless had significant repercussions. This was because, while the erosion of the lords of the Romagna had not brought about much stir on a peninsular level, Guidobaldo da Montefeltro’s loss of Urbino cast the Borgia in a different light. After all, although on a similar legal standing as the other signori, Guidobaldo was a condottiere of renowned prestige. The situation even suggested that the alliance between the Borgia and the French was at stake (Mallett 1987, pp. 204–5). When Louis XII suddenly arrived in Milan, many of the deposed vicars made their way to plead their case before the king, who was already irritated by the actions of Cesare’s captains in Tuscany, especially by Vitelli’s occupation of Arezzo. Alexander’s diplomatic undertakings continued relentlessly, accusing the Varano of Camerino of usurping lands which belonged to the papacy, and insisting that he and his son were not aware of what was happening in Tuscany (Giustinian 1876, vol. 1, pp. 21, 30). Cesare, however, judged it wiser to take matters in his own hands. Riding rapidly to Milan in disguise, he not only succeeded in being received by the king, but Louis warmly welcomed him: “he kissed him several times saying ‘it’s good that you’ve come my cousin and good relative’.”77 As Giustinian reported, “the pope was not very happy and is extremely concerned because the duke went without any consultation or participation of His Holiness.”78 Cesare was honourably welcomed by Louis; his bold intervention had succeeded in winning a great political victory. As Marco Pellegrini maintained, certain as he was of the inevitable war with Spain, Louis “would have delegated to him [Cesare] the central part of the peninsula, to rule in agreement with the papacy.” (Pellegrini 2009, pp. 99–100) Despite his initial concerns, Alexander conceded that “the duke has made very good conclusions with the king.”79 The judgement of Machiavelli in this regard could not have been more clear when he wrote:

On the Cardinal of Rouen telling me that the Italians did not understand war, I replied to him that the French did not understand the state; because, if they did, they would not have allowed the Church to reach such greatness.80

Cesare now had to face revolt from the captains who until that point had led most of his army, underlining how his ‘policy of pacts’ included his own men. As signori of small lordships, they feared that further Borgia expansion would come at the expense of their territories. Their alarm grew even further when, in return for Cesare’s aid in the looming war in Naples, “it appeared that the pope had some consent from the Most Christian King [Louis XII] over the things of Bologna.”81 At the Castle of La Magione, the commendator of which was Cardinal Giambattista Orsini, they agreed to unite in order to curb further Borgia expansion. One aspect often overlooked in this regard is that it was precisely the Guelf tradition which held the condottieri together. In fact, Machiavelli described how “They [the condottieri] debated the greatness of the duke and his character, and how it was necessary to restrain his appetite […] and they decided not to abandon the Bentivoglio family and to try to win over the Florentines.”82 Nevertheless, the conspiracy ended up having no meaningful protection by the greater powers. Machiavelli realised this when he wrote from Imola in October 1502 that “the king of France will help him [Cesare] with men and the pope with money.”83 Despite some considerable early successes by the condottieri, which even led to Cesare’s temporary loss of Urbino, Vitellozzo Vitelli placed his trust in the Florentines, who not only refused to assist Cesare’s enemies but even dispatched Machiavelli to inform him of the developing situation. With Florence neutralised, French backing secured, and papal aid guaranteed, Cesare swiftly regained the upper hand as he “provisioned the important territories with infantry, and supplied the rocche well.”84 The lack of cohesion between the conspirators was further evident in the fact that, once Paolo Orsini reached an agreement with Cesare at Imola in October, the terms also included that of helping him regain Urbino. Upon hearing of this, the pope simply smiled and described the conspirators as a “miserable and failed partnership.”85 As Cesare retook Urbino in December, Alexander retained a clear commitment to the French, especially in the expectation of further French support for his son, even if, the pope was keenly aware of the evolving state of affairs in Naples. In his conversations with Giustinian, Alexander spoke of “temporising” until spring, to observe how events unfolded. He also spoke of “providing for the needs of Italy”, an acknowledgment that the escalating Franco–Spanish struggle “to drive the other out of Naples” would render 1503 the decisive year for the political future of the peninsula (Giustinian 1876, vol. 1, pp. 243, 245–46). The pope understood that this struggle would be integral to the fortunes of the entire Borgia political project.

All this demonstrated that Alexander was thinking ahead, both regarding the fortunes of his son and those of the Papal States, whereas Cesare was increasingly concerned with his own political security. Cesare’s position in this regard emerges clearly in the way things turned out in the Bellissimo inganno di Sinigallia (31 December 1502), where the condottieri were met by Cesare’s celebrated ‘Deceit’. This included an important detail regarding the Orsini. Their uncomfortable association had already been uncovered when prominent Guelf allies such as Giovanni Bentivoglio were targeted by Cesare. In fact, when the Orsini had reached terms with Cesare, the agreement did not actually guarantee the security of those Guelfs who he still intended to attack (Shaw 2015, p. 236). This laid the groundwork for his inganno, which, with regard to the Orsini, unfolded as follows:

Paolo and the duke of Gravina Orsini were left alive, until the duke learned that in Rome the pope had arrested Cardinal Orsini, the archbishop of Florence, and Messer Jacopo da Santa Croce. At this news, on 18 January 1503, at Castel della Pieve, they too were strangled in the same manner.86

Cesare’s decision to ‘postpone’ the death of the Orsini, as opposed to the rapid execution of Vitellozzo Vitelli and Oliverotto Euffreducci, suggests that he did not share Alexander’s intention of bringing about their complete destruction. Alexander made this aim explicit when he expressed to Giustinian that he wanted to “ensure the State of the Church around Rome”.87 In fact, already by July 1502, Alexander was determined to “deprive the Orsini House of their state.”88 He also spoke of Louis XII’s consent for “redeeming all the territories of the Church, which malo modo are held by others.”89 This would have been the crowning of his policy of imposing direct papal sovereignty, given that much territory around Rome was still held by the Orsini. Alexander therefore continued to demand Cesare’s return to Rome, even if in early January the latter had taken Perugia in the name of the papacy. Alexander’s feud with the Orsini had been temporarily halted by Cesare’s accord with Paolo Orsini at Imola. Following Cesare’s ‘deceit’, his reluctance to completely ‘annihilate’ the Orsini could be explained in Machiavelli’s report, with one of Cesare’s secretaries telling him that: “Should the pope die, Cesare will need some friends in Rome.”90 This observation points once more to the inherent difficulty of founding a secular dynasty upon papal power, given the elective nature of papal succession (Carocci 2012, p. 81). Machiavelli in fact reported to the Dieci di Balìa of Florence how Cesare was well aware “that the pope can die any day, and that he needs to think before his death of laying for himself some other foundation, if he intends to preserve the states he now has.”91 As Cesare recognised that the backing of a Roman family such as the Orsini was necessary for his survival upon his father’s death, he proceeded with caution. Even after Paolo and Francesco Orsini were killed, Cesare refrained from a complete offensive against the dynasty, because several influential Orsini retained favour with the French king. Thus, while in February 1503, Alexander issued a public bando against the Orsini, declaring them “rebels of the state of the Holy Church and street robbers”92, Cesare excluded the important fortresses of Bracciano and Pitigliano from his operations. Bracciano was in fact held by Giangiordano Orsini, who was in the service of the king and like Cesare was a member of the Order of St. Michel, which prohibited fighting among its members in the field. Pitigliano, on the other hand, was held by Niccolò Orsini, who served as governor-general of Venetian forces. By attacking them, Cesare understood he would be deliberately provoking France and Venice. This was all to the frenzy of Alexander, who had recently sent artillery from Castel S. Angelo for besieging Bracciano (Burchard 1885, vol. 3, p. 237). Giustinian reported the pope’s reaction as follows:

The duke does not want, out of reverence for the French king, to move against Giangiordano. In due time we will carry out this enterprise without him […] If the king of France does not approve, we shall not hold back, for we want him to concern himself with the affairs of France, in which we do not involve ourselves, while we concern ourselves with the things of Rome.93

Alexander’s outbursts of anger towards his son marked a moment when Cesare’s aspirations, particularly his ambitions in Tuscany, came to diverge with his and now saw Cesare operate in almost complete autonomy. In fact, it saw Cesare turn towards Maximilian of Habsburg, Louis’s rival, and intrigue for the investiture of the Tuscan cities of Pisa, Lucca, and Siena (Pellegrini 2010, p. 240), with the pope sometimes complying and indicating such aspirations to Maximilian (Giustinian 1876, vol. 1, p. 454). Despite these growing divergences between Cesare and the pope, Cesare nonetheless returned to Rome, albeit reluctantly, and then laid siege to the Orsini stronghold of Ceri, which fell in April 1503, after an intense artillery bombardment. Upon Giulio Orsini’s submission, Cesare ordered that the town should not be sacked and had Giulio sent to Pitigliano, which was outside papal territory. It was only at this point that Ceri was surrendered to Cesare (Giustinian 1876, vol. 1, pp. 463–73). This episode again illustrates his careful handling of the Orsini. When Cesare had previously shown willingness to accept Louis XII’s mediation concerning Giangiordano, Alexander reacted by declaring that “having bloodied his hands with the Orsini, he must understand that he has accomplished nothing, unless he destroys them all.”94 These events show Alexander’s impulsive and resolute determination to advance his ambitions. His fluctuating temper emerges vividly in Giustinian’s dispatches, which see the pope greatly rejoice in the triumphs of his son, yet he would quickly fall into violent rages. This was the case, for example, in the week before the ‘massacre of Sinigallia’, when reports arrived regarding the unknown whereabouts of his son, to whom he was sending 1000 ducats daily. Upon receiving the news, the pope could not refrain from losing his temper and calling his son “with great rage and indignation […]the bastard son of a whore!”95 By contrast, Cesare was more vigilant, as demonstrated in the calculated execution of his inganno and the unpredictable execution of his lieutenant Ramirez de Lorqua, a move which led Machiavelli to remark “no one knows well the reason of his death, except that it has pleased the Prince so, who knows how to use and disuse men at his own convenience”.96 Contemporary voices stressed the tension between affection and fear that characterised Alexander’s attitude towards his son: “The pope loves and has great fear of his son the duke.”97

The differences between Cesare and the pope indicate that Alexander sought to deliver a decisive blow through a combination of his son’s military force and his own diplomatic manoeuvres. As Giustinian remarked, as opposed to Alexander, “the duke shows more reserve.”98 When in March 1503 Alexander announced his intention to create more cardinals in order to raise additional funds, this declaration was accompanied by the following statement:

He [the pope] said that he wanted to recover these funds for the needs and necessities required to uproot these bad thorns from this land, and acquire all these states for the Church, thereby leaving behind a legacy that so many of his predecessors had striven for yet had been unable to achieve.99

Confronted with such a situation, Lous XII intervened and pressured Giangiordano to hand him Bracciano and retire to France. This was an extreme measure intended to keep Cesare aligned with France at a moment when the situation in Naples was deteriorating (Mallett 1987, pp. 216–17). By that point, the cities of Bologna, Florence, and Siena, together with the Orsini, had appealed to France for assistance, whereas French military defeats in Naples suggested that the French alliance was encountering substantial constraints. The evident restrictions of the alliance were unfolding before Cesare’s eyes: after Pandolfo Petrucci, the dominant figure in Sienese government, and a participant in the conspiracy, was expelled from Siena in January 1503, Louis intervened and ordered his return, under French protection. Simultaneously, since December 1502, Alexander was increasingly troubled by the evolving political situation. He confided to Giustinian that “it would be bad for both of us if Span took over Naples, yet far worse if it were to fall into French hands”.100 However, Venice refused any form of alliance, intent as it was on moving south towards the Romagna at the first opportunity, and it disregarded Alexander’s probably sincere pleas, which called for the unity “of this poor Italy” (Giustinian 1876, vol. 1, p. 477). It is certain that, in the pope’s mind, this was inseparable from securing the fortunes of his son, whom he wished “placed in the arms” of Venice. The Serenissima, however, was unwilling to act as guardian of Cesare’s domains, with Giustinian speaking of his “juvenile fury”, which made Venice fearful.101 With hindsight, Venice’s rejection of any joint action, motivated by its own designs on the Romagna, placed it on course for the catastrophe of Agnadello in 1509. Given these circumstances, the Spanish monarchs seized the opportunity to propose a Spanish-papal alliance which would have included guarantees over the Tuscan cities of Siena, Lucca, and Pisa, which Louis XII had never allowed Cesare to incorporate, and which were negotiating an anti-Florentine alliance in collusion with the pope (Fernández de Córdova 2009, p. 54; Mallett 1987, p. 218). As Giustinian reported on 24 April, Alexander accompanied Cesare to Ceri, where news arrived that Louis had dispatched a messenger to Siena to ensure Petrucci’s wellbeing and had again written in favour of Giangiordano Orsini. At this, “the pope started to speak bad of the French, accusing them of ingratitude, insolence and avarice.”102

The shift in papal policy was evident when, during a consistory in May 1503, Alexander elevated five additional Spanish cardinals, bringing their total to sixteen (Mallett 1987, p. 218). Alexander’s growing distance from France received a powerful incentive from the military successes of Gonzalo de Córdoba over the French, especially after the Battle of Cerignola (28 April 1503). The pope began “showing little faith to the boasting of the French and saying the worst possible things about them.”103 In fact, in late June, Alexander asserted “that what the Spanish did is the will of God; and if God’s will is so, we should not desire otherwise”.104 It is difficult to determine which policy might have been taken from this point onwards, for while Alexander was reflecting on the possibility of Cesare receiving the investiture of the Tuscan cities along with an alliance with the Spanish monarchs, Louis handed over Alexander the rest of Giangiordano’s possessions (Shaw 1981, pp. 17–18).

While these developments were still in progress, the pope died on 18 August, leaving Cesare facing the existential crisis of any close papal relative. With the Spanish and French armies still fighting in Naples, Cesare was still, at least openly, committed to France, even if his support for a French candidate was an overestimation of his influence over the Spanish members of the Sacred College. As Guicciardini observed, Cesare could not totally rely on all the Spanish cardinals, “because many of them, unwilling to offend their king, would not be led to elect a French cardinal.”105 The day after Alexander died, Cesare met with Prospero Colonna and sent Cardinal Francesco Borgia to negotiate with the Spanish monarchs; he himself headed towards the French army camped at Nepi (Fernández de Córdova 2009, p. 56). Cesare’s dilemma suggested that he was well aware that he depended on Louis’s favour for keeping the Romagna. The same went for the Venetians, who upon the death of the pope, seized the opportunity to invade the region. Alexander foresaw this when he confided to Giustinian that “without the shadow and good will of your Republic, all of the duke’s labours would be in vain.”106 Cesare’s only hope rested in the outcome of the conclave and the willingness of the new pope to confirm his position. He himself had judged that having liberated the papal territories from ‘factions’ and ‘tyrants’, “a new pope would be grateful to him.”107

Cesare thus turned his attention to the conclave. The influence which he wielded on the Spanish cardinals in Rome was a significant measure of Borgia influence, yet everything depended on the favour of the new pontiff (Mallett 1987, pp. 252–61). This was recognised by Machiavelli during his legation in Rome in November 1503. Cesare was no longer a significant player and, as Machiavelli wrote, matters involving the Romagna were of secondary importance compared with those involving France and Spain (Machiavelli 1850, vol. 2, p. 372). Although Cesare was confirmed as gonfaloniere by Pius III, his political difficulty immediately resurfaced after the death of Pius less than a month following his election. Simultaneously, as early as September 1503, both France and Spain were competing for the services of the Orsini and not those of Cesare (Giustinian 1876, vol. 2, p. 210). Perhaps taking their Guelf heritage for granted, the French ambassador Louis de Villeneuve failed to match the offers of the Spanish, who proposed to the Orsini a contract for 500 men-at-arms to be shared between them (Giustinian 1876, vol. 2, pp. 237–38). In the end, in October 1503, Giulio Orsini and Paolo Orsini’s son, Fabio, settled their condotte with the Spanish, an agreement which eventually permitted them to share in the spoils of Spain’s victory by restoring their fortunes (Shaw 1981, p. 18). It was thus becoming increasingly clear that Cesare was a political nessuno, notwithstanding his influence over the Spanish cardinals and the garrisons in the Romagna manned by his Spanish fidelissimi. Machiavelli described Cesare during this time as “out of his mind, because he did not know what to do, as he was entangled and indecisive.”108 However, such judgement overlooked that Cesare had no hope beyond maintaining his position as the secular arm of a military autonomous Roman Church. This is why the Spanish cardinals under Cesare’s influence permitted the election of Julius II on 1 November. The new pope, however, immediately revealed his true intentions and ordered Cesare to surrender the fortresses of Cesena, Forlì and Bertinoro, which Cesare still held, fearing that even these would fall in the hands of the Venetians (Giustinian 1876, vol. 2, pp. 305–6; Guicciardini 1971, p. 575). In doing so, Julius shed light on the complexity of Cesare’s position as both gonfaloniere of the Church and duke of the Romagna. With this dilemma, he chose to prioritise the duchy. When he refused to hand over the fortresses, Julius ordered his arrest and appealed to the Spanish monarchs “in order to recover for the Church Imola, Forlì and Cesena which the duke of Valentinois has usurped” (Quoted in Fernández de Córdova 2009, p. 60). Recognising the difficulty of recovering the fortresses without offering terms, Julius agreed that Cesare be confined in the fortress of Ostia, under the supervision of Cardinal Carvajal. Once the fortresses were surrendered, Carvajal judged that the obligations of the agreement had been fulfilled and allowed Cesare to depart under a safe-conduct from Gonzalo de Córdoba, obtained for him by Cardinals Borgia and Remolins.

Wishing to maintain good relations with Julius II, the Spanish monarchs ordered Cesare’s arrest upon his arrival in Naples and had him imprisoned in Spain. After escaping in 1506, thanks to the support of Castilian nobles opposed to Ferdinand, Cesare made his way to the court of his brother-in-law John III of Navarre. As John’s captain-general, Cesare became embroiled in the region’s political struggles, which, like Italy, formed another theatre, albeit a minor one, where Spanish and French interests collided. Moreover, with Maximilian’s son Philip now ruling in Castile, Cesare’s position was in effect that of an imperial pawn against France (Adot Lerga 2005, p. 198). Furthermore, with the Treaty of Blois (1505), Louis XII and Ferdinand of Aragon came to terms over Naples (Mallett and Shaw 2014, pp. 80–81). Thus, Cesare saw in his campaign against the leader of the rebel army, Louis Beaumont, Count of Lerín, an opportunity for vendetta against Ferdinand (Fernández de Córdova 2009, p. 71). In the night of 11–12 March 1507, he was killed in an ambush during the Siege of Viana.

5. Conclusions

This article has examined the political position of Cesare Borgia, particularly in relation to his connections with France and, to a significant extent, Venice, his condottieri, and the Roman baronial families. Cesare was the product of a reinvigorated papacy that sought to harness energies unleashed by the Italian Wars. Nevertheless, the papacy remained encircled by longstanding political realities with which it had to continually come to terms. Through the creation of the Duchy of the Romagna, Cesare emerged as a signorial power in his own right, yet this was limited by his reliance on France, his relationship with the barons and above all, his dependence on the physical presence of his father, the pope. All these suggest that he may aptly be described as a ‘two-faced Janus’, the term employed to describe the Renaissance papacy itself as this study has demonstrated, from Alexander VI’s perceptions, in the domains of his son, the increase in the fortunes of the dynasty and the interests of the Papal States could converge effectively. This remained surely the case at least until 1503, when Cesare’s interests in Tuscany demonstrated a serious attraction to an area outside the Papal States, one to which the pope never seriously committed himself. It was in fact precisely at that moment that the limits of a papal–dynastic convergence were ultimately exposed. Although the Borgia political enterprise collapsed by the end of 1503, with the barons and the signori reclaiming their lost territories, Cesare’s experience demonstrated that the balance of power was visibly shifting. This is where the term ‘two-faced Janus’ becomes most effective. Indeed, Alexander had effectively drew the sword in imposing strong temporal undertakings over the Papal States. In doing so, he laid the foundations upon which Julius II later built, enabling the latter to take up that same sword and impose papal temporal sovereignty with lasting success. In this sense, the effects of this ‘Janus’ reveal that, although Cesare’s political position was cut down, parallel to this, the Papal States had gained politically. This was recognised by Machiavelli, who observed:

Although his intention [of Alexander] was not that of making great the Church, but the duke, he nonetheless made it return to greatness, which after his death, and the extinction of the duke, inherited his labours.109