Agathocles the Sicilian
Machiavelli cites Agathocles as an example of someone who attained his political control through crime. Agathocles lived from 361 to 289 BC and came from humble origins—his father was a potter. He rose up through the military ranks in Syracuse to become the praetor.

One morning, he assembled the members of the Senate of Syracuse and with one signal had all of the Senators and the town's richest people killed, leaving no one to oppose his political control. Machiavelli credits him for taking control of his own destiny.

Alexander the Great
Alexander the Great was a Macedonian ruler in the fourth century BC. He is used as an example by Machiavelli on how to divide and rule conquered territory.

Alexander VI
The father of Cesare Borgia, Rodrigo Borgia became Pope Alexander VI in 1492. Machiavelli notes that it was Alexander who helped propel his son into power. While Machiavelli acknowledges Alexander's role in Cesare's career, he credits Cesare with making the political decisions that accounted for his rise to power.

Cesare Borgia
Many of Machiavelli's examples of the effective ways for a prince to gain and retain power refer to practices he observed in his acquaintance with Cesare Borgia. He recounts that after being given the opportunity to rule Romagna, Borgia secured his position by following a set of standards that should be followed by any new ruler.

In particular, Machiavelli attributes four key ruling strategies to Cesare Borgia: eliminating all challengers to the throne, gaining the favor of the powers in Rome, especially the Pope; winning the support of the College of Cardinals; and defeating his enemies quickly and efficiently.

Rodrigo Borgia
See Alexander VI.

Charles VIII
Charles VIII was the French king who led the successful invasion against Italy in 1494. This invasion forced the Medici family to relinquish their control of Florence (which they later regained in 1512).

Liverotto da Fermo
Machiavelli uses Liverotto as an example of a prince who gained political power due to criminal means. An orphan, Liverotto was raised by his maternal uncle. After serving in the army, he returned to his uncle's home, asking if he could bring his entire army with him to impress his uncle's associates. After dinner, Liverotto took the powerful men aside, pretending that he had some secret to tell them. On his command they all were slaughtered. In the end, Liverotto's reign was stopped by one who could match him in deception and cruelty—Cesare Borgia.

Antonio da Venafro
Da Venafro was a professor of law in Sienna and minister of Pandolfo Petrucci, prince of Sienna. Machiavelli deems him a respected, intelligent advisor. His discussion about Antonio's good qualities and how they reflect on his prince represent a thinly-veiled attempt to stress how much Machiavelli's own good reputation and wise counsel would help the reputation of The Prince who would hire him.

Remirro de Orco
De Orco is Cesare Borgia's minister in Romagna. He ruled with ruthless power and was much hated. When he had outlived his purpose—that is, when the people threatened to rise up and kill him—Borgia had him killed. His body was left in the public square one morning, cut in half. In this way, Borgia was able to claim that the cruelty perpetrated against the people had come from Remirro, and not from him.

Ferdinand of Aragon
Ferdinand of Aragon was the king of Spain at the time that Machiavelli was writing The Prince. He was considered to be a new prince because he abruptly changed his style of ruling, becoming more aggressive later in his reign. His reputation grew by attacking Granada and by waging religious war against the Muslims that lived in Spain.

Louis XII
Louis was the French ruler from 1498 to 1515. Louis was an ally of the Venetians, and he is used as an example of how such alliances hurt city-states.

Girolamo Savonarola
Savonarola was a Dominican monk who preached to the people of Florence about self-government. He was instrumental in ousting the Medici family from power in 1498.

Valentino
See Cesare Borgia.