Masters of the Long Con

History isn't just full of brave heroes and clear-cut villains; it’s also packed with people who knew exactly how to pull the strings from behind the curtain. These figures didn't always need an army to get their way when they had a silver tongue and a knack for psychological warfare. You might find it fascinating how easily a single person could reshape the fate of an empire just by saying the right thing to the right person at the perfect time.

Elise Wolff on Wikimedia

1. Niccolò Machiavelli

There’s no better place to start than the original schemer himself. Not only did he write about gaining absolute power, but he also showed everyone that it’s better to be feared than loved. Truthfully, his tactics were so simple and crude that politicians still study him if they want to learn how to manipulate others.

Santi di Tito on Wikimedia

2. Catherine de' Medici

As a queen who found herself in a foreign court, she quickly learned that knowledge was her most valuable weapon against her rivals. She allegedly used a "flying squadron" of beautiful women to gather secrets and influence powerful men throughout the French aristocracy. It’s hard not to be impressed by how she managed to maintain control over a fractured country for decades while everyone was busy underestimating her.

Attributed to Germain Le Mannier on Wikimedia

3. Grigori Rasputin

Almost anyone could’ve taken advantage of Russia’s royal family, but they didn’t think a wild Siberian monk could. “Manipulate” is probably too weak of a word to describe how he tricked his way into becoming Vladimir and Alexandra’s personal buddy. He’s the perfect example of how a charismatic outsider can completely dismantle an establishment from the inside out.

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4. Cardinal Richelieu

Richelieu basically created the secret police to control his enemies and empower the king. Under his command, you’d honestly be scared to say anything against him because he somehow always knew what you were going to say. Nothing made Richelieu happier than watching powerful families tear each other apart.

Philippe de Champaigne on Wikimedia

5. Cleopatra

While she’s often remembered for her beauty, her real talent lay in her ability to convince the most powerful Roman leaders to do exactly what she needed. She knew how to stage grand entrances and use her intellect to forge alliances that kept Egypt independent far longer than anyone expected. You have to admit that winning over both Julius Caesar and Mark Antony takes a very specific kind of calculated charm.

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6. Thomas Cromwell

Serving as King Henry VIII’s chief minister wasn’t easy for a man of common birth. As the King’s right hand, Cromwell helped him through four divorces and created the English Reformation. Need someone subpoenaed? Thomas knew exactly whose legal strings to pull.

After Hans Holbein the Younger on Wikimedia

7. Livia Drusilla

Roman Emperor Augustus’ wife was rumored to be the true ruler of Rome for more than five decades. Legend has it that she would strategically eliminate anyone who got in the way of her son’s ascension. If you lived in ancient Rome, you would’ve known that crossing her was a very dangerous game that usually ended poorly for the other person.

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8. Talleyrand

The French diplomat knew how to play both sides so well that he served under the Monarchy, the Revolution, and Napoleon. Talleyrand was great at sniffing out political change and diving headfirst into the spotlight. Talleyrand is funny because he could sell out his leader one day and crawl back the next.

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9. Wu Zetian

As the only woman to ever officially rule China as an emperor, she had to be exceptionally clever to navigate a system that was built to keep her out. She utilized a ruthless secret police force to eliminate any officials who dared to question her authority or her right to rule. You’ll find that her path to the top was paved with carefully planned moves that left her opponents with no room to breathe.

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10. Joseph Fouché

He basically built the foundation for every surveillance state throughout history. As France’s chief of police during the revolution, he collected dossiers on pretty much everyone, including his bosses. You’d never want to be on his bad side because he always had enough dirt to bury anyone who tried to fire him.

Claude-Marie Dubufe / After René Théodore Berthon on Wikimedia

11. Agrippina the Younger

She was a master at the slow burn, taking years to position her son Nero as the successor to the Roman Empire. By secretly eliminating her husband, Claudius, once the paperwork was in order, she secured her place as the most powerful woman in the world for a brief time. Her story serves as a cautionary tale about what happens when you spend your life manipulating people who eventually learn your tricks.

Anonymous (Rome)Unknown author on Wikimedia

12. Madam C.J. Walker

Madam C.J. Walker wasn’t afraid to use manipulation to grow her million-dollar empire. She crafted a narrative so enticing that everyone wanted to be beautiful like her. You have to admire how she used social psychology to turn a small business into a revolutionary movement for Black women.

Addison Norton Scurlock / Adam Cuerden on Wikimedia

13. Otto von Bismarck

He famously claimed that the great questions of the day would be settled, but he usually used clever diplomacy first. He tricked his neighbors into declaring war on him so that he could look like the victim while expanding his own territory. It’s pretty wild to see how he single-handedly unified Germany by playing the rest of Europe like a giant chess set.

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14. Anne Boleyn

She didn't just catch the eye of Henry VIII; she completely changed the course of Western history by refusing to be just another mistress. By dangling the promise of a male heir and a legitimate marriage, she forced the King to break away from the Catholic Church. You can see how her calculated persistence made her one of the most influential and controversial figures of the Tudor era.

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15. Hernán Cortés

With only a few hundred men, he managed to topple the entire Aztec Empire by exploiting internal divisions and local myths. He convinced various indigenous groups to fight against their own leaders, essentially getting his enemies to do the hard work for him. It’s a dark look at how someone can use misinformation and psychological pressure to conquer a civilization.

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16. Mary, Queen of Scots

Mary constantly attempted to manipulate her way into the English throne through her cousin Queen Elizabeth I. Between constant family drama and plots, Mary was always playing the angles. You’ll notice that her brand of manipulation was often high-risk, which made her life incredibly dramatic and ultimately tragic.

Unidentified painter on Wikimedia

17. Vidkun Quisling

Quisling’s name literally became a synonym for traitor because of his Neville Chamberlain act with Hitler. The Norwegian politician deceived his government into allowing Germany to invade by pretending to be on Norway’s side. It’s a chilling example of how a person can use political rhetoric to hide a completely selfish and destructive agenda.

Riksarkivet (National Archives of Norway) from Oslo, Norway on Wikimedia

18. Mata Hari

She used her reputation as an exotic dancer to gain access to high-ranking military officials and gather intelligence during World War I. While historians debate how much she actually knew, she definitely understood how to use her persona to get men to spill their secrets. You’ve probably seen her depicted as the ultimate femme fatale, which was a character she carefully crafted herself.

Koene & Com / Batavia-Amsterdam on Wikimedia

19. P.T. Barnum

He was the king of the "humbug," knowing exactly how to manipulate the curiosity of the general public to sell tickets to his oddities. He didn’t care if people knew his attractions were fake; he just wanted them to spend money to draw their own conclusions. You can see his influence in modern marketing, where creating a spectacle is often more important than the actual product.

Brady-Handy Photograph Collection (Library of Congress) on Wikimedia

20. Empress Dowager Cixi

Empress Dowager Cixi manipulated her way from pawn to queen during China’s tumultuous Qing dynasty. From palace coups to foreign invasions, Cixi fought everyone’s moves and made her own. You’ll find that her ability to survive palace coups and international invasions makes her one of history’s most resilient power players.

John Yu Shuinling on Wikimedia