Niccolò Machiavelli

#1Florence, 1513.

#2A plot against the Medici had been uncovered, and investigators found a piece of paper with several names on it.

#3One of them was Niccolò Machiavelli.

#4Only months earlier, he'd been a senior official of the Florentine Republic, dealing with diplomacy, military affairs, and government business.

#5Now he was in prison.

#6He was arrested, locked up, and tortured. The main conspirators would be executed, and Machiavelli had no reason to assume he'd simply walk out.

#7Except there was a problem with the case against him.

#8There wasn't solid evidence that he'd actually joined the conspiracy. The list may have named people the conspirators thought could be useful after a successful overthrow.

#9Someone had written down Machiavelli's name.

#10That was enough to help put him in a torture chamber.

#11But what he did after getting out was stranger still.

#12Within months, Machiavelli was writing a short book about taking power, keeping it, using deception, inspiring fear, and knowing when a ruler might have to act in ways ordinary morality would condemn.

#13That book became "The Prince."

#14And Machiavelli hoped to get it into the hands of the family whose return had wrecked his political career.

#15Why would he do that?

#16Go back about fifteen years.

#17In 1498, Florence had just watched another political world collapse. The preacher Girolamo Savonarola, who'd become a huge force in the city's religious and political life, fell and was executed.

#18Around the same time, twenty-nine-year-old Machiavelli entered government service.

#19His job wasn't to sit around inventing political philosophy.

#20His job was politics.

#21He went on diplomatic missions. He dealt with the French monarchy. He watched the papacy. He followed wars, alliances, negotiations, and betrayals up close.

#22And then he was sent to deal with one of the most dangerous political operators in Italy.

#23Cesare Borgia.

#24Borgia was the son of a pope, and he was building power through a mix of military force, negotiation, intimidation, deception, and violence.

#25Machiavelli spent time around him in 1502.

#26At one point, commanders who had rebelled against Borgia came back, apparently thinking a reconciliation was possible.

#27Borgia received them.

#28Then he had them seized. Some were killed.

#29Machiavelli didn't just look at that and say, "What an evil man."

#30He wanted to know something harder.

#31Why did that work?

#32And then:

#33If Borgia was so good at building power, why did he eventually lose it?

#34"The Prince" didn't exist yet.

#35For Machiavelli, watching those questions play out in real life was part of the job.

#36Machiavelli spent about fourteen years serving the Florentine Republic.

#37He worried about Florence relying on foreign mercenaries and became deeply involved in building a citizen militia instead.

#38Then, in 1512, Florence ran into military power it couldn't stop.

#39Spanish troops attacked Prato. The city was brutally sacked, resistance collapsed, and Florence's leader Piero Soderini fled.

#40The Medici, who had been driven out years earlier, came back.

#41And just like that, Machiavelli's career broke.

#42One day he was reading state secrets. The next, he wasn't part of the government anymore.

#43He'd spent years studying what happened when rulers and regimes rose and fell.

#44Now the regime collapsing was his own.

#45And the following year, his name appeared on that piece of paper.

#46Machiavelli was arrested in the 1513 conspiracy investigation and tortured.

#47Other defendants were facing death.

#48And somehow, in the middle of that, he wrote verse.

#49One prison sonnet describes chains and misery with an oddly comic edge. He also appealed to Giuliano de' Medici over his situation.

#50The fear was real.

#51So was the humor.

#52Then Rome produced a twist.

#53Giovanni de' Medici was elected pope and became Leo X. Celebrations around the first Medici pope brought an amnesty, and Machiavelli was released.

#54So the Medici return had cost him his career. An anti-Medici conspiracy investigation had led to his torture. And the election of a Medici pope helped get him out.

#55He was alive.

#56He just didn't have a political life to go back to.

#57Machiavelli withdrew to his family's property near San Casciano, south of Florence.

#58His days looked nothing like the life he'd had in government.

#59He'd go out to the woods and talk with woodcutters. When travelers passed through, he'd ask where they'd been. He still wanted news. He still wanted to know what was going on in the world.

#60Later he'd head to the tavern, mix with people like a butcher and a miller, play games, swear, argue.

#61This was a man who'd recently been talking international politics with diplomats.

#62Now this was his day.

#63But night was different.

#64When Machiavelli came home, he'd take off the clothes he'd worn outside—the dirty, muddy ones.

#65Then he'd put on something else.

#66Clothes fit for court.

#67Only he wasn't going to a Medici palace.

#68He was going into his study.

#69There he opened Livy and other ancient writers. In a famous letter to his friend Francesco Vettori, Machiavelli described the experience as entering the courts of ancient men.

#70He'd question them.

#71Why did one state survive? Why did another fall? Why did an army fail? Why did people obey a ruler?

#72The answers came back through books written by people who'd been dead for centuries.

#73And for a few hours, Machiavelli said, he forgot his poverty and stopped fearing death.

#74The real courts had shut him out.

#75So every night, dressed for the occasion, he walked into a court of the dead.

#76That's where a little work called "De principatibus" began taking shape.

#77"The Prince."

#78Vettori was in Rome.

#79He was an old friend, and he was still inside the diplomatic world Machiavelli had lost.

#80The two kept writing to each other about the pope, France, war, Florence, the Medici. Then they'd veer into love affairs and jokes before swinging right back to politics.

#81Vettori didn't always agree with him either.

#82That made the exchange more useful, not less. Machiavelli had to explain himself, answer objections, keep pushing the argument.

#83Then, on December 10, 1513, he wrote the letter people still remember.

#84He described his nightly visits to the ancients and told Vettori he'd written a little work about principalities.

#85Machiavelli had been kicked out of political life.

#86But the political conversation never really stopped.

#87On one side were dead Romans.

#88On the other was a living friend.

#89"The Prince" was taking shape between the two.

#90It's tempting to turn this into a revenge story.

#91Maybe Machiavelli, furious after losing his career and being tortured, wrote poisonous advice meant to destroy the Medici from the inside.

#92Later readers have argued versions of that.

#93But there's no solid basis for treating it as the secret answer to the book.

#94Machiavelli's own letters point to a much simpler need.

#95He wanted back into politics.

#96He hadn't decided, "Fine, I'll forget politics and become a writer."

#97Politics was still the thing he thought he knew best.

#98He told Vettori that he wanted the Medici to find some use for him—even a small assignment.

#99He needed to show them he still had something to offer.

#100And he did.

#101Fourteen years of practical political experience.

#102Plus years spent reading the ancient world.

#103"The Prince" put those two things together.

#104At first, Machiavelli thought about presenting the work to Giuliano de' Medici. The final dedication went to Lorenzo di Piero de' Medici.

#105In that dedication, he talks about the kinds of gifts people normally bring princes—horses, weapons, precious things.

#106He had something else.

#107Knowledge of the actions of great men.

#108He'd gained it from long experience in contemporary politics and long study of the past.

#109The new regime had taken away his office.

#110So Machiavelli approached it with the most valuable thing he still had.

#111What he knew about power.

#112There are parts of "The Prince" that are genuinely uncomfortable.

#113Machiavelli doesn't assume a ruler can always behave like a conventionally good person.

#114If everyone else breaks promises, does the ruler have to keep every one? If preserving the state sometimes requires an act ordinary morality condemns, what then?

#115He says being both loved and feared would be ideal.

#116But if you can't have both, fear is safer.

#117Then he adds something people often leave out.

#118Don't become hated.

#119So no, it isn't just a celebration of cruelty and lies.

#120But you can't turn it into a harmless book about kindness either.

#121Machiavelli was willing to entertain a disturbing idea: being a good person and preserving a political order may not always demand the same thing.

#122That's part of why people have been fighting over this book for centuries.

#123And then there's another problem.

#124The same Machiavelli wrote the "Discourses on Livy," where he spends serious time thinking about republics, citizens, laws, institutions, conflict, and liberty.

#125So what was he?

#126A teacher of princes? A republican?

#127Maybe underneath both books was an even more persistent question.

#128Why do political orders survive, and why do they fall apart?

#129Before telling people what politics ought to look like, Machiavelli wanted to look at what people actually did when power was on the line.

#130This is the point where a clean comeback story is supposed to happen.

#131Disgraced politician writes brilliant book. The Medici recognize his genius. He comes roaring back.

#132That didn't happen.

#133"The Prince" didn't quickly restore Machiavelli to the political life he wanted.

#134So he kept writing.

#135The "Discourses on Livy." "The Art of War." And, from what can feel like another side of the same man, the clever and indecent comedy "Mandragola."

#136The longer he stayed outside the career he wanted, the more work he produced that later generations would remember.

#137But Machiavelli himself still wanted politics.

#138Eventually, relations with the Medici softened.

#139Around 1520, Machiavelli was officially commissioned to write the history of Florence. That became the "Florentine Histories."

#140Small public assignments began to come back too.

#141And in his later years, he grew close to Francesco Guicciardini.

#142Guicciardini wasn't a follower who nodded along with everything Machiavelli said. They argued, joked, and talked politics.

#143He also became an important link back to actual public work.

#144By 1526, Machiavelli had an official role connected to Florence's defenses.

#145Thirteen years earlier, he'd been sitting in the countryside hoping the Medici might give him almost anything useful to do.

#146Now he was discussing how Florence should defend itself.

#147He was fifty-seven.

#148The political Machiavelli was almost back.

#149Then the political world flipped again.

#150In May 1527, imperial troops sacked Rome.

#151Clement VII, the Medici pope, was badly weakened, and the shock hit Florence too.

#152The Medici were driven out again.

#153The republic came back.

#154This was the kind of government Machiavelli had served before 1512.

#155It seemed like the perfect opening.

#156He'd been a republican official. He'd lost his career when the Medici returned. He'd even been tortured after getting dragged into an anti-Medici conspiracy investigation.

#157Surely the restored republic would want him.

#158Except fifteen years had passed.

#159Machiavelli had accepted work under the Medici. Old political rivalries inside Florence were still there. The political map of 1527 wasn't the map he'd left in 1512.

#160On June 10, 1527, the restored republic did not give Machiavelli back his old secretarial post.

#161The republic had returned.

#162His place in it hadn't.

#163On June 21, 1527, Niccolò Machiavelli died.

#164He was fifty-eight.

#165Politics was the thing he'd spent his life studying in practice.

#166He'd watched men gain power. He'd watched them lose it. He'd watched republics collapse and the Medici return.

#167Then he lost power himself.

#168He kept trying to get back in. Eventually, he came close.

#169Then politics overturned itself one more time.

#170Eleven days after that final door closed, Machiavelli was dead.

#171And "The Prince" still wasn't a printed book.

#172The first printed edition appeared in 1532, five years after his death.

#173That's when the book's much longer political career began.

#174People read it. Condemned it. Banned it. Argued with it. Learned from it.

#175Some called it a handbook for rulers. Others saw a republican exposing the secrets of rulers.

#176Eventually, Machiavelli's own name became an adjective:

#177Machiavellian.

#178One night in 1513, after the courts of living rulers had shut him out, Machiavelli changed into his court clothes and opened the door to his study.

#179He went in to meet the ancient dead.

#180The book he started there never quite carried him all the way back into the courts of the living.

#181But after Machiavelli died,

#182the living kept walking into his study for centuries.

#183Cesare Borgia once welcomed commanders who had rebelled against him and let them believe reconciliation was possible.

#184Then he had them seized. Some were killed.

#185Machiavelli watched Borgia's methods at close range and later made him one of the most memorable cases in "The Prince."

#186But Borgia's own power began collapsing with startling speed after his father, Pope Alexander VI, died.

#187How did one of the boldest political operators Machiavelli ever watched fail to protect himself from his own downfall?