13 Mafia Bosses Who Defined The History Of The Mob

Published December 20, 2023
Updated June 7, 2024

Al Capone, The Infamous Chicago Mob Boss Known As “Scarface”

Mafia Boss Al Capone

Donaldson Collection/Michael Ochs Archives/Getty ImagesMob boss Al Capone became one of the most notorious gangsters of all time thanks to his great wealth and courting of the press.

Though he ran his operation out of Chicago, not New York, Alphonse “Al” Capone became one of the most infamous Mafia bosses of all time.

Born to Italian immigrants in Brooklyn in 1899, Capone’s inroads into the mob came at a young age when he and his brother Frank Capone started running errands for gangster Johnny Torrio. Though Capone only dabbled in gang activities as a youth, he quickly gained a reputation. In 1917, a man slashed Capone in the face after he’d made a remark about the man’s sister, leaving a scar and establishing Capone’s infamous nickname: “Scarface.”

Three years later, Capone left New York to join Torrio in Chicago, allegedly after members of the White Hand gang swore to get revenge after Capone beat one of their members. And when Torrio decided to return to Italy after surviving an attack and a stint in prison, Capone effectively became the boss of the Chicago underworld.

As he oversaw bootlegging, illegal gambling, and prostitution rackets, Capone became both wealthy and well-known. Many saw the round-faced and gregarious Capone as a Robin Hood type, especially as the country soured on Prohibition laws. But Capone had a capacity for violence that shocked even his most adamant supporters.

In 1929, a number of Capone’s rivals were brutally killed in what became known as the St. Valentine’s Day Massacre. Though Capone was conveniently out of town at the time, the murders shocked the public and ramped up the government’s efforts to arrest “Public Enemy Number One.”

Saint Valentine's Day Massacre

Bettmann/Getty ImagesAl Capone was conveniently out of town during the St. Valentine’s Day Massacre in 1929.

Still, Capone’s fall came in a surprising way. On June 5, 1931, he was arrested not for the St. Valentine’s Day Massacre murders or even his bootlegging activities, but on 22 counts of income tax evasion. After a stint in an Atlanta penitentiary, Capone was transferred to Alcatraz in 1934.

There, his health swiftly declined due to syphilis. Al Capone was released to a hospital in 1939 and eventually allowed to spend his final days with his wife Mae in Florida. Capone died at age 48 in 1947 as a shell of his former self.

author
Kaleena Fraga
author
A staff writer for All That's Interesting, Kaleena Fraga has also had her work featured in The Washington Post and Gastro Obscura, and she published a book on the Seattle food scene for the Eat Like A Local series. She graduated from Oberlin College, where she earned a dual degree in American History and French.
editor
Cara Johnson
editor
A writer and editor based in Charleston, South Carolina and an assistant editor at All That's Interesting, Cara Johnson holds a B.A. in English and Creative Writing from Washington & Lee University and an M.A. in English from College of Charleston and has written for various publications in her six-year career.
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Fraga, Kaleena. "13 Mafia Bosses Who Defined The History Of The Mob." AllThatsInteresting.com, December 20, 2023, https://allthatsinteresting.com/mafia-bosses. Accessed June 30, 2024.