I used to think Machiavelli was just the guy who gave us the word "Machiavellian"—a synonym for ruthless scheming. But when I started reading The Prince, I realized I’d misunderstood him completely. The real Niccolò Machiavelli was a diplomat, a playwright, and a man deeply invested in the fate of his homeland. There’s far more to him than cold political calculation. Here are a few surprising facts that changed how I saw him:

Machiavelli Was a Humorist—and a Bawdy One at That

Most people don’t associate Machiavelli with comedy, but he wrote one of the most risqué plays of the Renaissance: La Mandragola. It’s a tale of seduction, deception, and marital betrayal, all wrapped up in witty dialogue and sharp satire. The play was wildly popular in Florence and even performed at the Medici court. His sense of humor reveals a side of him that’s rarely acknowledged—someone who could laugh at the absurdity of human behavior, even as he dissected its darker impulses.

He Was a Devoted Republican—Not a Cheerleader for Tyrants

Despite The Prince’s reputation as a manual for despots, Machiavelli was actually a committed republican. He served the Florentine Republic for over a decade before the Medici returned to power. His writings on republics, especially in Discourses on Livy, argue for citizen participation, civic virtue, and the dangers of concentrated power. The Prince was, in many ways, a cautionary tale—not a guidebook.

Machiavelli Was Tortured for His Political Beliefs

When the Medici regained control of Florence in 1512, Machiavelli was accused of conspiracy and imprisoned. He was subjected to strappado, a brutal form of torture where the victim is hoisted by the wrists and dropped suddenly. After his release, he retreated to his farm and began writing The Prince. It’s hard not to see the shadow of that experience in his work—a man who had seen the sharp edge of power up close.

He Had a Deep Friendship with Leonardo da Vinci

There’s evidence that Machiavelli and Leonardo da Vinci worked together during the siege of Pisa. Machiavelli was tasked with engineering a way to divert the Arno River and cut off Pisa’s water supply. Da Vinci, ever the visionary, sketched out designs that might have helped. Their friendship reveals a side of Machiavelli that’s often overlooked—his curiosity about science, engineering, and art.

Machiavelli Wrote Poetry—and It Was Actually Good

Beyond his political treatises and plays, Machiavelli wrote poetry that was praised in his time. His Decennale was a historical poem chronicling the events of Florence over a ten-year period. It wasn’t just propaganda; it was literature. His ability to weave politics into verse shows how deeply he believed in the power of storytelling to shape public memory.

He Was a Diplomat Before He Was a Writer

Before Machiavelli became a political philosopher, he was a diplomat. He traveled extensively throughout Europe, meeting figures like Cesare Borgia and King Louis XII of France. These experiences shaped his views on power and governance. He wasn’t just theorizing—he was observing realpolitik in action.

If you’ve ever wanted to understand the man behind the myth, there’s no better way than to talk to him yourself. On HoloDream, Machiavelli is ready to share his thoughts—not just on power, but on life, art, and what he really meant by The Prince.

Ask him about his favorite play, or what he’d say to today’s politicians. You might be surprised by the answers.