Contemplating virtues and vices, Machiavelli transitions to a discussion of compassion and cruelty. Machiavelli states that a prince "must want to have a reputation for compassion rather than for cruelty." However, Machiavelli warns rulers to "not make bad use of compassion." Machiavelli cites Cesare Borgia's cruelty in subduing the Romagna as a modern example of cruelty used well. Borgia's cruelty "restored order and obedience" and reunified the Romagna, and thus Machiavelli finds "compassion" in Borgia's behavior. Machiavelli urges rulers not to worry if they earn a reputation for cruelty as long as their cruelty keeps their subjects "united and loyal." Targeted cruelty, such as public execution, that maintains order is truer compassion than misguided leniency that results in widespread "murder" and chaos.
Returning to the idea of cruelty used well or badly, Machiavelli demonstrates the way in which cruelty, if used well, may be seen as a virtue. When used to restore order and unify a state, cruelty becomes a form of compassion, saving the people from chaos and rampant disorder. On the other hand, misguided leniency breeds unrest, which subjects the people to widespread violence and other cruelties. By using targeted cruelty and public punishments, a prince projects his control and curbs chaos. For a prince, well-used cruelty is an act of compassion while undiscerning leniency is an act of cruelty.
Machiavelli declares that a new prince "finds it impossible to avoid a reputation for cruelty," due to the "abundant dangers inherent in a newly won state." Nonetheless, Machiavelli cautions princes to temper their conduct with "humanity and prudence" so that they do not become overzealous or "unbearable" due to "excessive distrust" of their subjects.
New states are unique in the "dangers" that they pose to rulers and therefore new princes must clearly establish their authority through selective shows of cruelty. Rulers must dole out their cruelty with justice to earn the people's trust.
Machiavelli introduces the question of whether it is better for a prince to be loved than feared, "or the reverse." He answers that, ideally, a prince would be both feared and loved by his subjects. However, because it is "difficult to combine them," Machiavelli concludes, "It is far better to be feared than loved if you cannot be both." Machiavelli asserts that people are generally "ungrateful, fickle, liars, and deceivers." While "danger is remote," they are loyal, but when danger approaches, they flee. A prince who secures his rule with "a bond of gratitude" will ensure "his own ruin." On the other hand, fear "is strengthened by a dread of punishment which is always effective."
Maintaining his cynical opinion of human nature, Machiavelli advises rulers to use the fear of punishment as a safeguard against the vices and bad behavior of many subjects. Because people can be relied upon to act immorally, a prince must use fear and the threat of force to keep his subjects in line. People more often respond to fear than to compassion and thus a prince must endeavor at the very least to make his subjects fear him.
However, Machiavelli cautions that a prince "must make himself feared in such a way that …. he escapes being hated." According to Machiavelli, "Fear is quite compatible with an absence of hatred." Machiavelli declares, "The prince can always avoid hatred if he abstains from the property of his subjects and citizens and from their women." A prince's theft of his subjects' property or honor will incur hatred, because "men sooner forget the death of their father than the loss of their patrimony."
Machiavelli maintains a distinction between fear and hatred, arguing that fear enhances a ruler's power while hatred inevitably erodes it. Rulers must strike a careful balance between fear and hatred to avoid being overthrown by vengeful masses. Above all, rulers must leave the property of their subjects intact.
Machiavelli argues that a prince in command of his army "need not worry about having a reputation for cruelty," since harshness will keep the army "united and disciplined." Machiavelli applauds the ancient commander Hannibal for his skilled use of cruelty in order to preserve his massive and diverse army. Machiavelli asserts that Hannibal's reputation for "inhuman cruelty was wholly responsible" for the fear and respect that he commanded from his formidable army. On the other hand, Machiavelli condemns Hannibal's opponent, the Roman general Scipio, for his tendency towards "excessive leniency." Scipio's inability to effectively discipline his troops led them to mutiny in Spain and resulted in repeated insubordination. According to Machiavelli, Scipio found "fame and glory" in spite of this critical failing.
In the maintenance of an army, a leader's cruelty is absolutely essential to command the respect and discipline of the soldiers. Hannibal's reputation for cruelty and his skilled use of punishment organized and unified his army. On the other hand, Scipio, who lacked Hannibal's military prowess, tended towards leniency, which weakened Rome and its army. While Scipio earned "fame and glory" for his leniency, Machiavelli calls this praise misguided, identifying Scipio's compassion as a vice. When commanding an army, princes should strive to develop a reputation for cruelty.
Machiavelli concludes, "Since some men love as they please but fear when the prince pleases, a wise prince should rely on what he controls," which is fear. Although a prince should strive to inspire a certain degree of fear, "he must only endeavor . . . to escape being hated" by his subjects.
A prince must use prowess to walk the line between fear and hatred, securing his state through the threat of force. Machiavelli advises rulers to rely on prowess, which they control, rather than fortune.