Nothing flattens fame like a mugshot. During Prohibition, the flashbulb in a police station captured bootleggers, mob bosses, rum-runners, and headline makers at their most ordinary. These stark portraits double as pop-culture artifacts, showing the faces behind speakeasies, gang wars, and the dry decade that rewired American nightlife.
This roundup revisits 20 mugshots from the Prohibition era, where each image feels like a time capsule of swagger, consequence, and surprising humanity.
1. John Dillinger
Dillinger was a Depression-era bank robber and jailbreak artist whose arrests turned him into America’s most wanted. He was shot and killed by federal agents outside Chicago’s Biograph Theater in 1934.
2. Alvin “Creepy” Karpis
Alvin was the mastermind of the Barker-Karpis gang and the last “Public Enemy No. 1” to be captured. After being nabbed in New Orleans in 1936, he spent decades behind bars, including a long stint at Alcatraz.
3. Al Capone
Capone was Chicago’s most notorious bootlegger and mob boss during Prohibition. He ultimately went down for income-tax evasion in 1931 and served time in federal prison.
4. George “Machine Gun” Kelly
“Machine Gun” was a Prohibition-era gangster whose fame peaked with the 1933 kidnapping of oilman Charles Urschel. He was captured soon after and drew a life sentence.
5. Ma Barker (Kate Barker)
Ma was the matriarch long linked to the Barker-Karpis gang in the 1930s. She was killed during an FBI raid in Florida, becoming a mythic figure of the era’s crime lore.
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6. Frank Costello
Known as the “Prime Minister of the Underworld”, Costello was a fixer who preferred influence over headlines. He did time for contempt of Congress and tax offenses after the Kefauver hearings made him a household name.
7. Jack “Legs” Diamond
Diamond was a dashing New York bootlegger who survived multiple attempts on his life. He was finally gunned down in 1931, not long after beating a major rap in court.
8. George “Bugs” Moran
Moran was the leader of Chicago’s North Side Gang and a bitter rival to Capone. He narrowly missed the St. Valentine’s Day Massacre and later served time for robbery.
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9. George Remus
Remus was a lawyer-turned “King of the Bootleggers” who built a liquor empire by exploiting legal loopholes. He was convicted on Prohibition violations and later made headlines for a sensational domestic tragedy.
10. Owney Madden
Madden was a New York mobster and a speakeasy kingpin behind the Cotton Club’s heyday. Earlier convicted of murder, he later shifted his operations south to keep a low profile.
11. Charles “Lucky” Luciano
Luciano was the architect of modern organized crime in New York. He was convicted in the 1930s on vice charges and was eventually deported.
12. Charles “Pretty Boy” Floyd
“Pretty Boy” was a bank robber mythologized as a Robin Hood figure during the Dust Bowl years. He was killed by law officers in Ohio in 1934 after a multi-state pursuit.
13. Joe Adonis
Adonis was a polished New York-New Jersey racketeer and close ally of Luciano. Repeated arrests and gambling cases trailed him, and he was ultimately deported to Italy.
14. Vito Genovese
Genovese was a hard-edged mob boss whose influence stretched from Prohibition into the postwar years. He was later convicted on federal narcotics charges and died in prison.
15. Johnny Torrio
Torrio was the strategic founder of the Chicago Outfit and mentor to Al Capone. After an assassination attempt and bootlegging charges, he faded from the spotlight but remained a power behind the scenes.
16. Hymie Weiss
Weiss was a North Side Gang leader who carried the fight to Capone’s doorstep. He was constantly in and out of police custody until he was cut down in a Chicago ambush in 1926.
17. Lester “Baby Face” Nelson
“Baby Face” was a volatile bank robber who briefly became Public Enemy No. 1 after Dillinger’s death. He died in a ferocious 1934 shootout with federal agents near Chicago.
18. Frank Gusemberg
Gusemberg was the enforcer of Moran’s crew and one of the victims of the 1929 St. Valentine’s Day Massacre. He was known to the police long before that day, and he refused to name his shooters as he lay dying.
19. Murray Humphreys
Humphreys was the Chicago Outfit’s smooth negotiator and fixer, known for being more suited to the boardroom than the back alley. His arrests for racketeering and tax evasion troubles followed him throughout his long career.
20. Vincent “Mad Dog” Coll
“Mad Dog” was a fearsome New York gunman tied to kidnappings and extortion during the beer wars. He was hunted by rivals and police alike, and was cut down in a Manhattan phone booth in 1932.
Explore more historical content:
If these stark flashbulb moments from the dry decade pulled you in, pour another round of vintage history with these 24 Vintage Photos That Perfectly Capture the Prohibition Era, or these 20 Photos of Prohibition-Era Bootleggers in Action (1920-1933). You can also try these 19 Eerie Photos of Speakeasy Crime and Mob Enforcers.
