Machiavelli highlights two ways of becoming a prince that "cannot altogether be attributed to fortune or to prowess." The first way is when "a man becomes prince by some criminal and nefarious method." The second manner is when "a private citizen becomes prince of his native city with the approval of his fellow citizens," as often happens in a democratic state. Focusing on the first method, Machiavelli states his intention to explore two examples, one ancient and one modern, "without otherwise discussing the rights and wrongs" of this method.
Machiavelli firmly separates morality from his discussion of men who win their states through "criminal" methods. Machiavelli refrains from ethical judgment of these princes, focusing instead on the advantages and disadvantages of their harsh tactics. Significantly, Machiavelli draws a distinction between these "criminal" methods and prowess.
Machiavelli introduces the ancient example of Agathocles, who rose from the "lowest, most abject condition of life" to become king of Syracuse (in Sicily). "At every stage of his career" Agathocles "behaved like a criminal," also possessing considerable "audacity and physical courage." Rising through the military ranks to become praetor of Syracuse, Agathocles decided to make himself prince. Assembling the Senate of Syracuse, Agathocles had his soldiers massacre the senators and richest citizens and seized the government of Syracuse. Machiavelli argues that Agathocles' success cannot be attributed to fortune, since his rise was marked by "countless difficulties." Similarly, his success cannot be attributed to prowess, since "it cannot be called prowess to kill fellow-citizens, to betray friends, [and] to be treacherous, pitiless, [and] irreligious." With his "brutal cruelty," Agathocles won power but not honor, and therefore he cannot be "honored among eminent men."
Although Machiavelli acknowledges Agathocles' "audacity and physical courage," he does not attribute Agathocles' rise to prowess, a term that Machiavelli reserves for rulers who win their states with a certain degree of honor. Recognizing the effectiveness of Agathocles' methods, Machiavelli nonetheless states that Agathocles cannot be "honored" with other able rulers. Machiavelli's refusal to attribute Agathocles' success to prowess functions as a sort of implicit criticism of his "treacherous" methods. Interestingly, this implicit criticism contradicts Machiavelli's earlier attempts to remove morality from the discussion of criminal tactics, though it may fit with Machiavelli's belief that a ruler cannot succeed by inspiring hate in those whom he hopes to lead.
Turning to the modern example, Machiavelli introduces Oliverotto of Fermo. Raised by his uncle Fogliani, a leading citizen of Fermo, Oliverotto was sent to serve as a soldier in his youth. Trained as a soldier and believing that "it was servile to take orders from others," Oliverotto hatched a plan to return to Fermo and seize it for himself. Returning to his childhood home, Oliverotto prepared a "formal banquet" to which he invited his uncle and other leading citizens. During the banquet, Oliverotto's soldiers "appeared from hidden recesses" and killed Fogliani and all the other guests. With his opponents eliminated, Oliverotto "strengthened his position" further by creating "new civil and military institutions." A year later, Cesare Borgia and his troops trapped Oliverotto and his troops, eventually capturing and killing Oliverotto.
Although Machiavelli does not praise the treacherous Oliverotto, he does reference the skillful way in which Oliverotto "strengthened his position" by establishing new legal and military institutions. By creating and staffing new institutions, Oliverotto fortified his new standing by ensuring that his recently installed ministers and military commanders remained loyal to and dependent on him. Like Agathocles, Oliverotto's methods were criminal but quite successful. Stopping short of praise, Machiavelli does recognize Oliverotto's cunning ability to remove his opponents.
Machiavelli considers how it was that Agathocles and others like him were able to "live securely" in their own country after committing "countless treacheries and cruelties." Machiavelli argues that it is "a question of cruelty used well or badly." Cruelty is used well when "it is employed once for all, and one's safety depends on it, and then it is not persisted in." Cruelty is used badly when it "grows in intensity" and causes a prince's subjects to "never feel secure" with regard to their ruler. Machiavelli advises rulers to inflict violence "once for all" so that people will then "forget what it tastes like and so be less resentful." Violence must be inflicted once, but by contrast benefits to one's subjects must be doled out gradually and "in that way they will taste better."
With these closing remarks, Machiavelli blurs the typical distinction between virtue and vice by arguing that cruelty can be used both well and badly. Machiavelli advises rulers to employ cruelty wisely to manage their relationship with their subjects. Violence used poorly will only enrage the people and thus weaken a ruler's position. However, cruelty used well forms the cornerstone of a prudent prince's safety and security, allowing him to strengthen his position and his state. When used sparingly by a wise prince, cruelty can be a virtue.