| Sumario: | In late August 1530, three Florentine merchants formed a partnership specifically to wager on the outcome of the papal election following the death of Pope Sixtus V. Thanks to the survival of an account book compiled by one of the three, Dinozzo Lippi, their undertaking can be examined in detail. This article analyzes the account book within the contexts of Lippi's commercial career, the tradition of betting on papal elections, the specific historical circumstances of the September 1590 conclave, and the practices of commercial speculation in Renaissance Italy. I argue that it reveals not only the internal functioning of the papal betting market but also the intellectual habitat for financial risk taking in premodern Europe prior to the development of mathematical probability theory. Lippi's careful accounting of bets demonstrates how merchants made qualitative probabilistic decisions, revealing how an investment made on the identity of the next pope was no less rational nor speculative than an investment made in currency exchange or maritime insurance.
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