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Between 1463 and 1467, Cardinal Bessarion (ca. 1403–1472) constructed one of the biggest funerary chapels in Quattrocento Italy. Based on newly discovered archival material, this article will examine how Bessarion’s self-fashioning for the afterlife in his chapel built on existing patterns of patronage in the basilica of Santi Apostoli while consciously standing in contrast to them. I will argue that competition for space and visibility within the basilica of Santi Apostoli were key factors informing Bessarion’s choices for his chapel during its construction. A deeper understanding of this process will provide new insights into the power structures behind the erection of one of the largest funerary chapels of the Quattrocento.