Name-dropping:
Niccolò Machiavelli (NEEK-o-low mak-ee-a-VELL-ee) (1469–1527).
Florentine writer and diplomat whose The Prince we were all supposed to read in high school but didn’t, because while it is extremely short, it somehow also manages to be extremely boring.

When to Drop Your Knowledge:
Every cocktail party has its evil dictator: the one who yells when speaking softly would suffice, monopolizes the resources by constantly hovering around the food and drink, and ruthlessly murders perfectly pleasant conversations with unfunny jokes. The Cocktail Party Dictator may believe his malevolent antics are justified by Machiavelli—but with your knowledge of the first great political philosopher, you’ll be able to explain that Machiavelli wasn’t nearly as evil as his totalitarian disciples.

The Basics
Born to a prominent family down on its luck, Niccolò Machiavelli was, in life, little more than a midlevel diplomat in Florence. Think of him as similar to the U.S. Ambassador to Fiji. Can’t recall the name of the U.S. Ambassador to Fiji? That’s our point.

And had Machiavelli kept his government job, he likely never would have become famous. His early writings, which had scintillating titles like “On the Way to Deal with the Rebel Subjects of the Valdichiana,” were forgettable. But in 1512, the Medici family returned to power in Florence, and Machiavelli was fired. Accused of conspiring against the Medicis, he was briefly tortured and thrown into jail. Unable to find a job after his release, Machiavelli had time on his hands, so he wrote two works that would change the world: Discourses on the First Ten Books of Titus Livius and The Prince.

In the Discourses, Machiavelli asserted his belief in democracy as the best possible form of government. He did, however, endorse a kind of amorality—the
Discourses mark the first appearance in political philosophy of the idea that the ends justify the means. He believed Florence was too weak and corrupt to support a republic. So in 1513 he wrote The Prince, his most famous and most controversial work, a kind of primer for would-be tyrants. What Italy needed, Machiavelli believed, was a “redeemer,” a man who would rule with an iron fist, crush dissidents, build up the military, and rein in the malevolence in human nature. In short, you have to screw the people to save the people.

Machiavelli never achieved wide fame for his work during his life, but The Prince has been in print ever since–and more than a few modern dictators have used it as a blueprint, particularly in postcolonial Africa and South America. Because The Prince is so quotably blunt, Machiavelli has been a bit unfairly maligned. His contributions to philosophy and political theory are immense–he was the first person, for instance, to note the now trite maxim that history repeats itself. So really, a truly Machiavellian person isn’t evil so much as relentlessly pessimistic and consistently unlucky–your basic philosophical Rodney Dangerfield.

The Quotable Machiavelli
On Friendship:
“You should keep your friends close, and your enemies closer.”

On How Not to Have a Happy Marriage:
“It is better to be feared than loved.”

On the Second Amendment:
“Before all else, be armed.”

On Acting Rashly:
“The wise man does at once what the fool does finally.”

One Bad Marriage
Machiavelli was married for 25 years to Marietta Corsini. It rather goes without saying that he cheated on her frequently. (The ends of wanting to make out, after all, justify the means of breaking your marriage vows.) Marietta was a loving and devoted wife, but it seems Machiavelli never thought much of marriage: In one of his plays, a devil chooses to return to the fires of hell rather than spend time with his wife.

Machiavellian
One of the surest paths to immortality is to get a word named after you–but sometimes the price of fame is association with malevolence. Below, enjoy our guide to bad words and the bad people they’re named for.

Machiavellian: Meaning “characterized by cunning and treachery.” From the fellow in question.

Draconian: Meaning “extremely, unnecessarily harsh.” From seventh-century Athenian politician Draco, whose codification of Athen’s legal code was considered too severe.

Luddite: Meaning “one who stubbornly opposes technological advancement.” From Ned Ludd, a British workman who supposedly destroyed weaving equipment around 1779.

Bowdlerize: Meaning “to censor or prudishly edit.” From Bowdler, who, in keeping with the excessive prudishness of the times, published an expurgated version of Shakespeare in 1818.

Conversation Starters
◆ Some argue that “Old Nick,” a slang term for the devil, derived from Machiavelli’s first name, Niccolò, which would mean that we have Machiavelli to blame not only for despotism, but also for the Adam Sandler vehicle Little Nicky. Which is the greater crime? We’ll leave that for you to decide.

◆ Although he courted the favor of several popes, Machiavelli didn’t think much of Christianity, what with its emphasis on meekness, humility, and justice. But then, the popes of the time weren’t such great Christians either. Leo X, who gave Machiavelli a job, spent the Vatican into bankruptcy and then tried to get out of it by selling get-out-of-hell-free cards called indulgences. The moral vacuity of the indulgences led, at least in part, to the Protestant Reformation that would irrevocably split the European Church.

◆ Besides being a revolutionary political philosopher, Machiavelli was also a published poet. It’s hard to imagine a guy like Machiavelli writing good poems—fortunately, he didn’t. His poetry is universally regarded as drivel.

◆ Tupac Shakur, the thinking man’s gangster rapper, read from Machiavelli extensively during a stint in prison. Late in his ca- reer, Tupac began recording under the name Makaveli. Why the changed spelling? Well, maybe Tupac wanted to play on the gangster slang word “mack,” which can mean flirting (to put it mildly) or a gun (Mac-10). But conspiracy theorists who believe Tupac’s death was faked point to the fact that Makaveli is an anagram of “K, am Alive.” Not the strongest evidence perhaps, but how’s this: Since his (purported) death in 1996, seven (seven!) new Tupac albums have been released.