Chronicling the interiors and exteriors of selected abandoned buildings in Sydney, this article examines the problem of memory in spaces that are not only isolated and devalued, but often have played no role in the life of the casual visitor or observer. How can the ruins of someone else’s past be made to speak, and how might contemporary ruinscapes reveal a different way of engaging with the past in urban space, particularly in one of the “youngest” cities in the world: a city not defined by decline; constantly undergoing redevelopment; and known more for contemporary architecture than contemporary ruin? Through describing personal encounters with each site, this paper adopts the attitude of Benjamin’s collector who encounters old books in a way that does not consider their use-value but instead sees them as fated objects, encountered as ephemeral remnants of the past. Like the salvaged but outmoded book, the modern ruin is just as much a site in which history is played out as any house of parliament or mainstream newsroom. Further, history need not be the dominion of those things and people that speak loudly and clearly—it is equally constituted by boundless, amorphous, liminal, discarded, rejected, silent things—in this case, ruined buildings of a recent, remembered and accessible past.