Police Chief AND Mob Boss?

You might think you’re busy balancing a day job and a hobby, but some people in history took multitasking to a whole new, often scandalous level. It’s fascinating to realize that some of the most respected pillars of society were actually moonlighting as the very villains they swore to protect others from. This list explores twenty instances where historical figures maintained two identities that were completely at odds with each other, making for some truly wild stories.

Lynn Gilbert on Wikimedia

1. William Brodie: Deacon and Burglar

William Brodie maintained two careers: one as a well-respected Scottish cabinetmaker by day, and one as a thief who targeted his wealthy clients by night. He would wait until they slept before sneaking into their homes to copy their keys and make off with their valuables. He got away with it for years before being caught after a crime gone wrong.

Stephencdickson on Wikimedia

2. Vidocq: Criminal and Criminologist

As a young man, Eugene Francois Vidocq was a career criminal who escaped prison more times than anyone else in French history. Later in life, he founded both the first private detective agency and France’s national police force. Oh, the irony.

Marie Gabriel Coignet (1793-?) on Wikimedia

3. J. Edgar Hoover: Lawman and Rule-Breaker

J. Edgar Hoover was horrified by the thought of the FBI being linked to any criminals. The whole point was to show the nation that law enforcement always caught the bad guys. However, Hoover secretly blackmailed government officials with illegally gathered evidence. Hypocrite.

Marion S. Trikosko on Wikimedia

4. Belle Boyd: Debutante and Confederate Spy

Belle Boyd lured Union officers into giving up their secrets when she was just a teen socialite. She would flirt and charm her way into military dinner parties, then ride off into the night to pass along intelligence. Her greatest asset was her ability to convincingly play the damsel.

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

5. Charles Ponzi: Businessman and Fraudster

Charles Ponzi appeared to investors as some kind of math wizard who could turn small investments into fortunes. In reality, he stole their money and paid old investors with fresh funds in one of the earliest pyramid schemes. That kind of scam is still called a “Ponzi scheme” today.

Boston Library (NYT); en.wikipedia.org on Wikimedia

6. James Armistead Lafayette: Slave and Double Agent

Working as an enslaved man for a British general gave James Armistead the perfect cover to act as a spy for the American Revolutionaries. He managed to feed the British false information while sending the real plans back to the Marquis de Lafayette, directly contributing to the victory at Yorktown. It’s an incredible story of someone navigating two worlds.

Unknown engraver, based on painting by John B. Martin on Wikimedia

7. Chevalier d'Eon: Diplomat and Female Spy

The Chevalier d’Eon lived most of his life as a man but ended up popularly considered to be female. This French diplomat served in many high-ranking political roles for years before “transitioning” and living as a woman. Nobody really knows which gender was the truth.

Thomas Stewart on Wikimedia

8. George Orwell: Imperial Policeman and Anti-Authoritarian

Writer Eric Blair once worked as part of the British imperial policing forces in Burma. Enforcing the King’s law made him miserable, motivating him to leave the force and become Orwell, one of history’s most outspoken authors against authoritarianism. The contradiction between those two sides is fascinating.

BBC on Wikimedia

9. Mata Hari: Exotic Dancer and Double Agent

Think the story of Mata Hari is already known? Born Margaretha Zelle, she danced her way into the hearts of nearly every European military during WWI. Allegedly accepting funds from both the French and Germans, she sold information to both sides.

Koene & Com / Batavia-Amsterdam on Wikimedia

10. Robert Hanssen: FBI Agent and Soviet Spy

Anyone working at the FBI between 1970 and 2001 might have worked alongside a mole. For over 20 years, Robert Hanssen was selling American secrets to Russia while the FBI was tasked with finding him. He was literally trying to hunt himself down.

Federal Bureau of Investigation (FBI) on Wikimedia

11. Benedict Arnold: Hero and Traitor

Benedict Arnold began the Revolutionary War as one of America’s top generals. However, when he felt he wasn’t given enough credit by Congress, he betrayed his country and went straight to King George. Americans still use his name today as a synonym for traitor.

Thomas Hart on Wikimedia

12. Benjamin Thompson: Scientist and Loyal Spy

Benjamin Thompson made huge strides in the field of thermodynamics, but he also spied for the British during the American Revolution. Using coded invisible ink messages, he passed intelligence to the Crown throughout the war. Eventually, he moved to Europe and became a count.

Not specified[1][2] on Wikimedia

13. Christopher Marlowe: Playwright and Secret Agent

While writing some of the most influential plays of the Elizabethan era, Christopher Marlowe was likely working for Queen Elizabeth I’s secret service. Scholars believe his frequent travels and brushes with the law were actually cover for intelligence work against Catholic conspirators. His mysterious death in a tavern brawl might have actually been a political assassination.

anonymous  on Wikimedia

14. Thomas Jefferson: Freedom Writer and Slave Owner

Thomas Jefferson wrote the document that changed the world into one nation, but he kept hundreds of slaves on his own property. He somehow managed to maintain the public persona of a freedom fighter while morally compromising himself in private.

Rembrandt Peale on Wikimedia

15. Kim Philby: British Intelligence Officer and KGB Mole

Kim Philby worked his way up to head the MI6 intelligence bureau in Britain. However, he was a loyal communist feeding every bit of intelligence he could to the KGB throughout his career. When he defected, the truth came out, and world governments were changed.

Scanned and processed by Mariluna on Wikimedia

16. Alice Roosevelt: President’s Daughter and Rebel

Alice Roosevelt was the darling of the American public, but her father, Teddy Roosevelt, famously said he could either run the country or control Alice, but not both. She broke every social rule for women. Her public role as a diplomat’s wife was often just a front for her witty, rebellious, and politically savvy private maneuvers.

Unknown photographer on Wikimedia

17. Harry Houdini: Magician and Fraud-Buster

Harry Houdini was an escape artist and magician, but he had a secret side job exposing spiritualists. During the Spiritualism movement, he attended psychics’ shows to uncover their tricks and reveal them to the public. Skeptic.

Unknown authorUnknown author on Wikimedia

18. Julia Child: Famous Chef and Intelligence Officer

Long before she was teaching the world how to cook French food on television, Julia Child worked for the OSS during World War II. She helped develop a shark repellent that saved sailors and worked in secret communications across Asia. It’s hard to imagine the cheerful television personality also being an essential part of the American war effort.

FerEstrada on Wikimedia

19. Richard Nixon: President and Conspirator

Richard Nixon promised to heal a broken nation with decades of conservative leadership after the upheaval of the 1960s. Instead, he privately gathered a list of political enemies and devised a plan to spy on them. The scandal ruined his presidency.

Louis Fabian Bachrach, Jr. on Wikimedia

20. Elmyr de Hory: Artist and Forger

Elmyr de Hory painted professionally for years but was known more for his copies of famous artists’ works. He forged paintings by Matisse, Picasso, and several others to sell to unsuspecting museums and collectors. The fraud was fueled by his fabricated artist connections until they caught on.

JanManu on Wikimedia