Vespasiano da Bisticci (1421-98), whose busy bookstore brought together most of the great minds of Florence, was a life-long friend of Donato di Neri Acciaiuoli. This essay will examine their relationship. It was in his capacity as merchant that Vespasiano's association with Donato began, but over time it developed into a true friendship. Their correspondence covers the period from 1446 to 1463 with the bulk of the surviving letters dating from the year 1448-49.