Last Updated on September 30, 2025 by Matt Staff
The mugshots from this time are more than simple police photos. They capture hardened expressions, quiet defiance, and lives lived outside the law. Some of these men became legends, others faded into obscurity, but all of them left their mark on a country struggling with crime and corruption. Here are 20 unforgettable faces from the Prohibition era.
1. Al Capone, 1930
Capone rose to infamy in Chicago’s bootlegging scene, building a criminal empire through illegal alcohol, gambling, and violence. His 1930 mugshot shows the face of a man who controlled the city’s underworld with ruthless efficiency, and didn’t seem intimidated by the law at all.
2. Earl “Hymie” Weiss, 1926
As a rival mobster to Capone, Weiss was deeply involved in gang wars and organized bootlegging. His arrests reflected a life constantly at the edge of the law, fighting for dominance in Chicago’s criminal landscape.
3. George “Machine Gun Kelly” Barnes, 1933
Known for his daring robberies and high-profile kidnappings, Kelly’s violent methods earned him notoriety. His mugshot marks a career defined by audacious crimes and eventual capture by federal agents.
4. Frank Gusenberg, 1929
A member of the North Side Gang, Gusenberg was a key player in Chicago’s violent Prohibition conflicts. His criminal life ended during a bloody shootout, immortalizing him as a symbol of the era’s brutal gang wars.
5. George “Bugs” Moran, 1929
Moran’s long feud with Capone made him a central figure in Chicago’s gangland violence. Arrests and near misses dotted his life as he navigated bootlegging, theft, and murder plots.
6. John Dillinger, 1924
Dillinger became America’s most wanted bank robber in the 1930s. His mugshots capture the charm and menace of a criminal who repeatedly outsmarted law enforcement before his dramatic downfall.
7. Benjamin Siegel, 1928
Siegel’s early career in bootlegging and extortion set the stage for his later Las Vegas ventures. Arrests during this period reflected his involvement in organized crime and his growing reputation as a ruthless enforcer.
8. Joe Masseria, 1922
Boss of New York’s early mafia scene, Masseria controlled bootlegging operations and violent rackets. His mugshot symbolizes a man who thrived on power, intimidation, and strategic criminal alliances.
9. Johnny Torrio, 1936
Torrio, Capone’s mentor, orchestrated Chicago’s underworld with a mix of savvy business sense and brute force. Multiple arrests punctuated his career, mostly tied to liquor smuggling and gang violence.
10. Dutch Schultz, 1931
Schultz made his name in bootlegging and illegal gambling. Known for his temper and brutality, his arrests marked a life defined by confrontations with both rivals and authorities.
11. Owney Madden, 1931
Madden dominated New York’s Harlem underworld with bootlegging, gambling, and nightclub operations. Arrests were a constant, reflecting the high stakes of his criminal enterprises.
12. Jack “Legs” Diamond, 1929
Diamond’s criminal career included bootlegging, armed robbery, and repeated run-ins with law enforcement. His mugshots reveal a life lived in perpetual conflict with the law.
13. Lester “Baby Face” Nelson, 1931
Known for his youthful appearance and violent bank robberies, Nelson was a feared outlaw. His arrests punctuated a career marked by audacious crimes and a deadly reputation.
14. Robert Anastasia, 1932
Anastasia’s involvement in organized crime included extortion and bootlegging. His mugshot captured a life steeped in secrecy, loyalty, and lawless ambition.
15. Charles “Lucky” Luciano
Luciano revolutionized organized crime, building a national syndicate that thrived on bootlegging and gambling. His arrests were stepping stones in a rise to criminal infamy.
16. Joe Aiello, 1930s
Aiello engaged in violent power struggles over Chicago’s Italian bootlegging operations. Arrests documented his relentless ambition and deadly approach to rival gangs.
17. Joe Adonis, 1937
A major figure in New York’s organized crime network, Adonis orchestrated bootlegging, gambling, and extortion. His mugshot reflects decades spent maneuvering the criminal underworld.
18. Carmine Galante, 1930
Galante’s early criminal life involved smuggling and organized crime in New York. Arrests punctuated a rise to power that would later dominate the mafia scene.
19. Frank Costello, 1935
Costello excelled in bootlegging and gambling operations, earning the nickname “Prime Minister of the Underworld.” His arrests show a life carefully balanced between power and prosecution.
20. Sidney “Razor” Kelly, 1926
Kelly’s violent reputation and involvement in organized crime made him a target for law enforcement. This mugshot captured the defiance of a man who thrived on fear and intimidation.
Want to check out more vintage mugshots?
Take a look at 20 Historical Mugshots from the Early 1900s, or check out 21 Mugshots from the Turbulent Phases of the 1970s. Finally, if you want to see mugshots from the 1950s, check out 20 Fascinating Mugshots from the Fabulous Fifties.
