This essay questions the seemingly laudatory judgment of Cesare Borgia in The Prince, chapter 7, by highlighting its emphasis on Borgia's dependence on the arms of others, which Machiavelli equates with “fortune.” During their encounters in 1502–1503, Machiavelli became keenly aware of Borgia's dependence on his papal father, on France, and on mercenaries. The praise of the “foundations” Borgia allegedly laid to remedy this dependence (including a fantasized conquest of Tuscany) is not Machiavelli's own assessment but the voice of Borgia's self-dramatizing and self-deceiving exaggerations. Knowing the weakness behind Cesare's bravado, Machiavelli could not have considered him the model of the “new prince,” still less of the “redeemer” invoked in chapter 26. On the contrary, Borgia is the negative model of the new prince who depends on the arms of others, inevitably fails, and blames fortune misconstrued as malicious fate.