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In his 1907 essay on Francesco Sassetti’s last injunctions to his sons, Aby Warburg argued that the Florentine banker represented a transitional moment between a medieval and a more modern mentality. Warburg suggested that Sassetti captured something of the creative and commercial energy that drove the cultural and economic flourishing of fifteenth-century Florence. This paper returns to Sassetti’s memorandum situating it within a broader context that reflects both what was exceptional about Renaissance Florence and what was typical about it, in relation to those cultural and commercial energies. It situates the Florentine Renaissance within Jack Goody’s interpretation of mercantile culture as an element common to pre-modern cities across Eurasia. In addition, however, it also integrates with recent work highlighting the significant role of the city in the development of concepts of value and risk in the fifteenth and sixteenth centuries.