Machiavelli defended a massacre as more merciful than a city's refusal to act

Niccolò Machiavelli tells two stories in close succession, both about men who seized power through outright treachery and murder, and he uses them to make an argument that still makes readers uncomfortable.

The first is Agathocles, a potter's son who worked his way up through the army to become a military commander in Syracuse, then decided he wanted to be its ruler outright. He arranged with a Carthaginian general to back him, called an assembly of the senate and the wealthiest citizens as if for ordinary business, and had his soldiers kill every one of them on a signal. He then took the throne without opposition, fought off the Carthaginians twice, and even invaded Africa to force them into a treaty. Machiavelli refuses to call this virtue in the sense of admirable character; slaughtering fellow citizens and betraying friends isn't glory. But he also refuses to pretend it wasn't effective.

The second is Oliverotto of Fermo, who invited his own uncle and the leading men of his city to a banquet, walked them into a private room under the pretext of discussing politics, and had soldiers hidden there kill them all. He ruled the city for a year, growing formidable to his neighbors, before Cesare Borgia had him strangled.

Machiavelli's real question isn't whether these acts were monstrous. It's why some rulers who commit atrocities hold onto power safely for years, while others, guilty of far less, get destroyed by their own subjects the moment things get difficult. His answer is that cruelty can be well used or badly used. Well-used cruelty happens once, out of genuine necessity, and is never repeated; afterward the ruler works to convert whatever benefit he can to the people he governs. Badly used cruelty starts small and keeps growing, because the ruler never draws a line under it.

To make the point land, Machiavelli turns it around and points at his own city. Florence, wanting to avoid a reputation for cruelty, refused to act decisively and let Pistoja tear itself apart in factional violence instead. Machiavelli's blunt conclusion is that Florence's leniency was, in its actual effects, far less merciful than anything Cesare Borgia did in Romagna, because Borgia's harshness fell on individuals, while Florence's inaction let an entire town destroy itself. Injuries, he insists, should be inflicted all at once, so their bitterness fades, while benefits should arrive gradually, so people keep feeling them.

If a genuinely necessary hard decision is in front of you, take it once, completely, and don't drag it out into repeated smaller doses that never let people move past it. Resist letting severity become routine, because the instant it turns into an ongoing pattern rather than a one-time correction, it stops producing order and starts producing resentment instead. Once the hard part is done, follow it with real, visible improvement, delivered gradually so people actually feel it building rather than dumped all at once. And before you congratulate yourself for staying gentle, ask honestly whether your reluctance to act is quietly doing more damage than the harsh decision you're avoiding would.