Rebels Who Broke All Rules

You don't get called infamous for pocketing candy. It takes chaotic cleverness and just enough luck to go too far and ensure that you're remembered for years to come. Some outlaws wore armor, and a few others wore their charm. But one commonality across all of them is that none of them played by the rules. Curious who they are? Here are the stories of the 20 most infamous outlaws.

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1. Eustace The Monk: C. 1170–1217

He once took holy vows and then traded them for chaos at sea. Known for switching allegiances between England and France, Eustace built a pirate fleet that disrupted trade and tormented coastal towns. His cunning earned him a reputation as a strategic maritime outlaw in Europe.

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2. Ishikawa Goemon: 1558 – 1594

Robbing the rich, he broke into heavily guarded samurai estates and slipped out with gold, says the folklore. In the rigid Sengoku period of Japan, Goemon's high-profile thefts and open contempt for authority made him a symbol of rebellion that the ruling class couldn't ignore.

Utagawa Toyokuni I on Wikimedia

3. Blackbeard: 1680 – 1718

Sailors swore the smoke from his beard made him look half-human, half-hellspawn. Even though his theatrics were legendary, it was his blockade of Charleston's harbor and command of a pirate flotilla that sealed his place in history. Blackbeard (Edward Teach) stole cargo and disrupted entire economies with style and strategy.

Engraved by Benjamin Cole[1] (1695–1766) on Wikimedia

4. D. Turpin: 1705 – 1739

Turpin's reign of terror included armed highway robberies and holdups between London and York. These crimes were ruthless and methodical, targeting merchants and travelers alike. His notoriety stemmed from his transgressions and execution after being imprisoned at York Castle.

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5. Jonathan Wild: 1682 – 1725

In early 18th-century London, Jonathan Wild turned the law upside down. He collected fees from victims desperate to retrieve stolen goods while secretly working with the very thieves who had committed those felonies. His cunning web of control blurred the line between felons and crime fighters.

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6. Jesse James: 1847 – 1882

Jesse James fused guerrilla warfare skills with high-stakes robberies that made him one of the most infamous figures of the Wild West's violent underworld. A daring raid on Northfield's First National Bank shook Missouri and sealed his gang’s reputation for lawlessness and downfall.

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7. Billy The Kid: 1859 – 1881

He was a young man who turned to gunslinging in the violent chaos of New Mexico. Billy the Kid's daring jailbreaks and deadly involvement in the Lincoln County War made him infamous as a sharpshooter and symbol of frontier rebellion.

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8. Belle Starr: 1848 – 1889

Oklahoma's "Bandit Queen" earned her reputation as an accomplice to outlaw gangs rather than wielding weapons herself. Belle Starr's ability to steer and influence a male-dominated underworld made her a rare criminal figure. She mysteriously passed away in 1889.

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9. Ned Kelly: 1854 – 1880

Kelly's self-crafted armored rebellion played out across northeastern Victoria's farming towns, such as Greta and Glenrowan. He became notorious for confronting colonial forces alongside Irish settlers and left behind a legacy as both a villain and a folk hero.

Charles Nettleton (attributed) on Wikimedia

10. Butch Cassidy: 1866 – 1908

Leading the Wild Bunch, Butch Cassidy's outlaw reputation grew through high-stakes robberies across Wyoming and Utah. Known for slipping away with clever disguises, he left lawmen frustrated. It is said that he died in Bolivia, but his story remains one of the most mysterious.

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11. Joaquín Murrieta: 1829 – 1853

Masked raids on mining camps and stagecoaches across California's Sierra foothills marked Joaquín Murrieta as a phantom of Gold Rush fear. To Anglo settlers, he was a bandit. To many Mexicans, he was the resistance. Fables grew from his campaign against injustice, fed by fiction.

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12. Bonnie And Clyde: 1910 – 1934 And 1909 – 1934

Gas stations in Texas. Banks in Oklahoma. Grocery stores in Missouri. Bonnie and Clyde's robbery trail spanned the American South and Midwest during the Great Depression. The pair's signature move was fast getaways in stolen Fords. A camera left behind in Joplin gave the press everything they needed to put names, faces, and flair to the country’s newest crime duo.

Photo by one of the Barrow gang on Wikimedia

13. John Dillinger: 1903 – 1934

Dillinger robbed banks by studying them, slipping past alarms with practiced speed. Some of his escapes embarrassed law enforcement so often that the media likened him to a "Public Enemy No. 1". In a final insult to his captors, Dillinger escaped Crown Point Jail in 1934 using a wooden pistol he himself carved behind bars. 

FBI on Wikimedia

14. Al Capone: 1899 – 1947

The Outfit ran bootleg routes from Canada to Chicago, with Al Capone at the helm, turning Prohibition into a booming underground empire. His lavish lifestyle and tight grip on Cicero's politics made him a media fixture. But finally, his time arrived. He became the first mob boss brought down by the federal tax code.

Chicago Bureau (Federal Bureau of Investigation) - Wide World Photos. on Wikimedia

15. Baby Face Nelson: 1908 – 1934

Born Lester Gillis, he hijacked getaway cars and stormed banks alongside the Dillinger Gang. His boyish face hid a hair-trigger temper and a willingness to shoot first. After gunning down FBI agents in Wisconsin and Illinois, he gained darker fame than Dillinger—more violent, less controlled, and far harder to predict.

FBI on Wikimedia

16. Veerappan: 1952 – 2004

He turned India's sandalwood forests into a battleground. Veerappan built a vast smuggling empire protected by loyal informants and deep jungle cover. He eluded multiple state forces for decades, and in 2000, his kidnapping of actor-politician Rajkumar proved just how untouchable he’d become.

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17. Zheng Yi Sao: 1775 – 1844

She commanded ships by leading the Red Flag Fleet, a pirate armada that outnumbered most navies. Her grip on the South China Sea disrupted imperial trade by taxing merchants. Zheng Yi Sao rose from being a mere brothel worker to the most feared woman in maritime crime.

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18. Pearl Hart: 1871 – After 1901

Stagecoach robbers weren't rare in the Wild West, but a woman behind the holdup was. In 1899, Pearl Hart stunned the public by robbing a stage outside Globe, Arizona. Her defiant courtroom speeches and flair for drama secured her a lasting spot in outlaw legend.

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19. Pancho Villa: 1878 – 1923

In 1916, Villa stormed the U.S.–Mexico border with a guerrilla army by launching a surprise attack on Columbus, New Mexico. That raid—combined with his control over northern Mexico—sealed his reputation not just as a revolutionary but as a volatile force that defied international boundaries.

D.W. Hoffman, an El Paso photographer on Wikimedia

20. Anne Bonny: 1702 – 1782 Or 1697 – 1782

She stormed ships in men’s clothing, armed and dangerous, fighting alongside Jack Rackham’s crew in the Caribbean. Anne Bonny wasn’t remembered for mercy or a long career but for defying expectations with violence and standing out as one of the few women among brutal 18th-century pirates.

Engraved by Benjamin Cole[2] (1695–1766) on Wikimedia