Pope Alexander VI
One of only two figures in The Prince who appear enough times and are treated in enough breadth to constitute “characters” in an otherwise largely narrative-free work. The father of Cesare Borgia, Alexander, originally named Rodrigo Borgia, was Pope from 1492 to 1503. During that time, he did much to strengthen the papacy and augment the power of the Church.
Cesare Borgia
The son of Alexander VI, Cesare rose to power quickly and shrewdly, only to lose his winnings through a stroke of bad luck. Machiavelli sympathizes with his defeat, and holds him up as an example of someone who is both prudent and clever in their acquisition of power.