Agathocles the Sicilian
Machiavelli uses Agathocles as an illustration of someone who achieved political power through criminal actions. Agathocles, who lived from 361 to 289 BC, came from modest beginnings—his father was a potter. He climbed the military ranks in Syracuse, eventually becoming the praetor.

One morning, he gathered the Senate members of Syracuse and, with a single signal, had all the Senators and the wealthiest residents killed, leaving no one to challenge his authority. Machiavelli commends him for seizing control of his fate.

Alexander the Great
Alexander the Great, a Macedonian ruler in the fourth century BC, is cited by Machiavelli as an example of how to effectively divide and govern conquered territories.

Alexander VI
Rodrigo Borgia became Pope Alexander VI in 1492 and was the father of Cesare Borgia. Machiavelli notes that Alexander played a significant role in advancing his son's power. While acknowledging Alexander's influence, Machiavelli credits Cesare for making the strategic political decisions that led to his rise.

Cesare Borgia
Machiavelli frequently refers to Cesare Borgia when discussing effective methods for a prince to gain and maintain power. After being given control of Romagna, Borgia secured his position by adhering to a set of principles that any new ruler should follow.

Specifically, Machiavelli attributes four key strategies to Cesare Borgia: eliminating all rivals, securing the favor of influential figures in Rome, particularly the Pope; gaining the support of the College of Cardinals; and swiftly and efficiently defeating his enemies.

Rodrigo Borgia
See Alexander VI.

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

Liverotto da Fermo
Machiavelli uses Liverotto as an example of a prince who obtained power through criminal means. Orphaned and raised by his maternal uncle, Liverotto returned home after military service, requesting to bring his entire army to impress his uncle's associates. After dinner, he took the powerful men aside, pretending to share a secret, and on his command, they were all killed. Ultimately, Liverotto's rule ended when he was outmatched in deception and cruelty by Cesare Borgia.

Antonio da Venafro
Antonio da Venafro was a law professor in Sienna and a minister to Pandolfo Petrucci, the prince of Sienna. Machiavelli regards him as a respected and intelligent advisor. His discussion of Antonio's virtues and how they benefit his prince subtly suggests that Machiavelli's own reputation and wise counsel would greatly enhance the standing of The Prince who employed him.

Remirro de Orco
Remirro de Orco served as Cesare Borgia's minister in Romagna, ruling with an iron fist and earning widespread hatred. When his usefulness ended—specifically when the populace threatened to revolt—Borgia had him executed. His bisected body was displayed in the town square one morning. This allowed Borgia to shift the blame for the cruelty inflicted on the people onto Remirro, distancing himself from the atrocities.

Ferdinand of Aragon
Ferdinand of Aragon was the king of Spain during the period Machiavelli wrote The Prince. He was regarded as a new prince due to his abrupt shift in governance, becoming more aggressive later in his rule. His fame grew through his conquest of Granada and his religious campaigns against the Muslim population in Spain.

Louis XII
Louis XII ruled France from 1498 to 1515. He allied with the Venetians, serving as an example of how such alliances could be detrimental to city-states.

Girolamo Savonarola
Girolamo Savonarola was a Dominican monk who advocated for self-governance in Florence. He played a key role in the expulsion of the Medici family from power in 1498.

Valentino
Refer to Cesare Borgia.