Citizens who become princes through luck or the favor of others find it easy to acquire their states, but difficult to keep them. They are not used to being in command, and they have no armies of their own.
Francesco Sforza became a prince by his own strength and kept his state. Cesare Borgia became a prince by his father's influence, and, despite his best efforts, could not maintain his state after his father's influence failed. This was not his fault, but was caused by extraordinary bad luck. Alexander VI wanted to make his son great, but had no troops he could rely on. Alexander allowed the French into Italy in exchange for the use of their troops to conquer the Romagna region. Borgia succeeded and made more conquests, but worried about the French king and the loyalty of his Roman troops, led by the Orsini family. He lured the Orsini leaders with gifts and promises of friendship, then killed them all. He won the loyalty of the people in Romagna. He had at first found the Romagna to be lawless, so he put Remirro de Orco in charge of restoring order, which he did well. However, Remirro de Orco was so cruel that everyone hated him, so to deflect bad feeling from himself, Borgia had him publicly executed.
At this point Borgia had laid good foundations for his power. But abruptly Alexander died, and Borgia himself was extremely ill. Borgia then made a mistake by not preventing the election of a Pope hostile to him. In short, Borgia was a model prince and did all things well, except for his poor judgment about Julius II, which caused his downfall.
Although Machiavelli offers an example of a prince who rose to power through his own ability in Francesco Sforza, he devotes most of this long chapter to the analysis of the career of Cesare Borgia, whose rise depended on the favor of others, namely his powerful father, Pope Alexander VI (born Rodrigo Borgia). Machiavelli's admiration for Borgia shines throughout the description. He sees in Borgia a model for all princely conquerors. Machiavelli had an opportunity to personally observe this dynamic Duke when he was sent by the Florentine council to negotiate with Borgia about relations with Florence. Machiavelli was on this mission when Borgia lured his enemies to the city of Senigallia and had them strangled, and Machiavelli spoke with Borgia about the incident. Borgia was by all accounts ruthless, ambitious, and boundlessly energetic, possessing a forceful personality that impressed those around him. It is no accident that these are the same qualities possessed by Machiavelli's ideal prince.
Borgia radiates virtù, but in the end it is not enough to save him, because he remains dependent on the power and influence of his father. Pure bad luck—his father's sudden death and his own unexpected illness—puts him on the path to ruin. The dangers of dependency on others will become a key point in Machiavelli's arguments, one he emphasizes later in his discussion of armies.
Machiavelli's endorsement of Borgia's tactics, including deceit, brutality, and betrayal of his own agents, is enthusiastic. One may be more inclined to judge Borgia as a heartless master manipulator, expertly playing factions against one another, using those around him as needed and disposing of them as they become inconvenient. But for a brief period, he was stunningly successful, on the verge of consolidating his hold over Italy—and success in controlling the state is all that matters in Machiavelli's analysis. He will be more explicit in Chapter 18 on how necessary it is for a prince to be deceitful when circumstances call for it, and in Chapter 17 how cruelty is often better than mercy to preserve the peace and order of the state.
Duke Valentino Cesare Borgia was often referred to as Duke Valentino or Duke Valentinois, a title he was granted by Louis XII of France.
Orsini and Colonna rival families of the Roman aristocracy, both enormously powerful in Italian politics. The Orsini family, in particular, was a bitter opponent of the Borgias, and Cesare Borgia ordered at least three of the leading Orsini family members to be killed.
College of Cardinals an assembly that is responsible for electing a successor when a Pope dies.
San Piero Machiavelli refers to a number of cardinals (Colonna, San Giorgio, Ascanio, and Rouen) who were potential candidates for Pope, calling some of them by the names of their churches. "San Piero" was Giuliano della Rovere, who become Pope Julius II. "Rouen," whom Machiavelli thinks Borgia should have contrived to elect, was Georges d'Amboise.