Last Updated on October 7, 2025 by Matt Staff
But behind the smoke and swagger was a harsher truth. These men and women lived fast, hunted by both the police and their own people. The rare photographs in this collection pull back the curtain on that world, revealing faces hardened by poverty, adrenaline, and fame.
Each of these photos is able to tell its own story about captivating instances of danger as well as defiance. They provide glimpses into a time period when the line between villain and hero blurred in the shadow of America’s darkest years. Let’s dive into 20 photos of Depression-era gangsters now.
1. Bonnie and Clyde
Bonnie Parker and Clyde Barrow were America’s most infamous outlaw couple, blazing a trail of robberies and murders across the Midwest during the early 1930s. Romanticized by the media, they became symbols of rebellion during desperate times, though their spree ended violently in a police ambush in 1934.
2. John Dillinger
Known as “Public Enemy No. 1,” John Dillinger was a daring bank robber who captivated the public with his charisma and bold escapes. He became a folk hero to many struggling Americans but was ultimately gunned down by the FBI outside a Chicago theater in 1934.
3. Charles “Pretty Boy” Floyd
Charles “Pretty Boy” Floyd was a Depression-era “Robin Hood” figure who robbed banks across Oklahoma and reportedly destroyed mortgage records to free farmers from debt. Despite his reputation as a folk hero, he died in a hail of gunfire during an FBI chase in 1934.
4. Baby Face Nelson
Born Lester Gillis, “Baby Face Nelson” was one of the most violent outlaws of the Depression era. A volatile member of the Dillinger gang, he was responsible for multiple murders, including those of federal agents, before dying in a furious gun battle in 1934.
5. Alvin Karpis
A key figure in the Barker-Karpis Gang, Alvin “Creepy” Karpis specialized in bank robberies and kidnappings. Known for his intelligence, he became the last public enemy captured alive, arrested by the FBI in 1936. He later passed due to natural causes in 1979.
6. George “Machine Gun” Kelly
George Kelly Barnes earned his nickname from his favorite weapon, the Thompson submachine gun. A bootlegger and kidnapper, he became infamous for abducting oil tycoon Charles Urschel in 1933, which was the crime that landed him in Alcatraz.
7. Ma Barker
Kate “Ma” Barker was the matriarch of the infamous Barker-Karpis Gang, often portrayed as the brains behind her sons’ criminal activities. While some debate how involved she really was in planning robberies and kidnappings, she became a symbol of ruthless family loyalty and was killed alongside her son, Fred, in a deadly FBI shootout in 1935.
8. Thomas James Holden
Holden operated as a getaway driver and accomplice in several high-profile robberies for the Holden-Keaton Gang in the Midwest. He avoided prison for years but was eventually arrested after a botched heist.
9. Blanche Barrow
The wife of Buck Barrow, Blanche, joined the Barrow Gang during their violent run through the South. Though not a killer herself, she endured several deadly shootouts and was eventually captured, serving time in prison before turning her life around.
10. Al Capone
Al Capone, known as “Scarface,” was the infamous leader of the Chicago Outfit during the Prohibition era. His empire thrived on bootlegging, gambling, and murder, making him Public Enemy No. 1. Despite his criminal activities, Capone was a folk hero to many during the Great Depression. He was eventually convicted of tax evasion and sentenced to 11 years in federal prison, serving time at Alcatraz before his release due to health issues.
11. Earl “Hymie” Weiss
Hymie Weiss was a Polish-American mob boss who led the North Side Gang in Chicago. He was a rival of Al Capone and was known for his violent tactics. Weiss was assassinated in 1926, after his own assassination attempt on Al Capone.
12. Vincent “The Schemer” Drucci
Vincent Drucci, also known as “The Schemer,” was a member of the North Side Gang and later became its leader after the death of Hymie Weiss. He was involved in various criminal activities, including bootlegging and gambling.
13. Harry Pierpont
Harry Pierpont was a mentor and partner to John Dillinger, helping organize several major bank heists. Smart and ruthless, he was executed in 1934 after a failed escape from the Indiana State Prison.
14. Charles Makley
A charming and smooth-talking member of Dillinger’s gang, Charles Makley participated in multiple bank robberies across the Midwest. He was captured and killed while attempting to escape from prison in 1934.
15. Russell Clark
Russell Clark served as a loyal getaway driver and lookout for Dillinger’s crew. Though less violent than his partners, he was deeply involved in the gang’s operations and spent decades in prison after his capture.
16. Frank Nash
A lifelong criminal and escape artist, Frank Nash was one of the most notorious figures of the 1930s underworld. His death during an attempted rescue in Kansas City sparked the infamous Kansas City Massacre, changing FBI tactics forever.
17. Frank Nitti
Frank “The Enforcer” Nitti was a member of the Chicago Outfit and served as its leader after Al Capone’s imprisonment. He was involved in various criminal activities, including extortion and murder. Nitti’s reign ended when he took his own life in 1943.
18. Jack “Legs” Diamond
A flashy and unpredictable New York bootlegger, “Legs” Diamond thrived during the Depression, running liquor, gambling, and racketeering operations. Despite surviving several assassination attempts, his luck ran out when he was shot to death in 1931.
19. Dutch Schultz
Born Arthur Flegenheimer, Dutch Schultz built a criminal empire in New York through bootlegging, extortion, and control of the city’s numbers racket. His violent ambitions eventually led to his assassination by other mobsters in 1935.
20. Charles “Lucky” Luciano
Luciano reshaped organized crime by establishing the modern American Mafia structure. Though more businessman than outlaw, his influence on bootlegging and gambling made him one of the most powerful figures of the era. This photo was taken during his exile while in Sicily.
Want to see more content from the years of the Great Depression?
Check out 20 Toys From the 1930s That Should’ve Come With Warning Labels, or take a look at 15 Rules 1930s Factories Made Workers Obey. Finally, if you want to see colorized photos from the depression, check out 20 Colorized Photos From The Great Depression.
