Cesare Borgia isn't on death's door when his father Alexander IV dies. He is alive and well, manages the Papal elections, and continues his expansion. Machiavelli believes that Cesare is the Italians best hope of unification, and when Cesare makes it clear that he is going after the city, Machiavelli brings the city peacefully into Cesare's expanding polity, and become Cesare's chief political adviser, acting as his "Prime Minister" if you will. Machiavelli's radical ideas about the use of citizen-soldiers is seen as one of the building blocks of Borgia's Italian state . . .