Andreas Palaeologus, the claimant to the Byzantine throne who died in Rome in 1502, has generally been portrayed as an immoral and extravagant playboy who squandered his generous papal pension on loose living and eventually died in poverty. This article seeks to make a departure from the traditional view of Andreas in two ways. First, on the basis of evidence drawn from the Papal archives, it will be argued that there were other reasons for the financial difficulties of this exiled prince. Secondly, his years of exile in Rome represent a continuation of the policy pursued by the Palaeologus family for a period of over a century and mark its ultimate failure.