21 Photos of Old-School Gangsters and Street Gangs

A black-and-white split image: Left—five men in suits and hats pose by a sign saying “Hotel Happy”; Right—an older man in sunglasses and suit walks, surrounded by men and photographers.

Before gangsters were glamorized by movies and myth, they were known (and feared) as shadowy figures carving out power in cities like Chicago and New York. From prohibition-era mobsters slinging underground booze to neighborhood crews doing the dirty work of organized crime, these old photos capture the grit and swagger that defined the underbelly of life in America and around the world. It also reveals how poverty and a lack of opportunity gave rise to the mafia — a world built on blood oaths, loyalty, and ambition.

1. ‘A Sharply-Dressed Al Capone and the Fellas, 1930s’

Five men in suits and hats pose in front of a rustic wooden building with a sign reading “Hotel Hot Springs in Happy.” Two are seated on a bench, three stand behind them, all looking at the camera.
jocke75/Reddit.com

2. Mugshots of Two Smooth-Looking Criminals Linked to the Razor Gangs in Sydney, Australia, Circa 1920

Two men in suits and hats sit side by side against a dark backdrop. One sits with arms crossed and a tilted head; the other sits upright with hands on his lap. Both stare seriously at the camera.
gatman02/Reddit.com

3. ‘Chicago Street Gang, Circa 1915’

A black-and-white photo of eight young men in suits and hats. Two are seated in front, while six stand behind them. They are indoors near barred doors or windows, posing seriously for the camera.
oldsoul8789/Reddit.com

4. A Gangster Fires a Thompson Submachine Gun as Bullets Fly, 1930s

A man aiming a gun
UserDeleted/Reddit.com

5. An Undercover Cop Punches a Knife-Wielding Thug in Glasgow, Scotland, 1971

A man in a long coat punches another man in midair on a busy street, while a crowd of people watch the confrontation in the background.
UserDeleted/Reddit.com

6. Notorious Mobster Sonny Franzese (Center) Walks With Detectives in New York City, 1960s

Three men in dark overcoats and suits walk down a city sidewalk, flanked by tall buildings. The central figure walks confidently, while the two men on either side appear to be escorting him.
xtalaphextwin/Reddit.com

7. Mobsters Hide Their Faces During Al Capone’s Trial in Chicago, 1931

A group of men in suits sit closely together in a courtroom, hiding their faces behind hats or hands, while a few others stand in the background observing.
BrorBrander/Reddit.com

8. Mob Boss Frank Costello Testifies Before the Kefauver Committee in Washington D.C., 1951

A man in a suit sits at a table with a vintage microphone in front of him, looking slightly to the side with a serious expression. The background is blurred and dimly lit.
snortingking/Reddit.com

9. John Gotti and Fellow Mobsters Pose for a Snap in Prison, 1960s

Six men stand together outdoors in casual clothing, posing and smiling for the camera on a sunny day, with buildings visible in the background.
UserDeleted/Reddit.com

10. ‘New York Street Gang, 1970s’

A group of eight young adults pose together in front of a worn building, wearing casual and punk-inspired clothing, denim vests, and accessories. Some look directly at the camera, while others appear relaxed.
mousetrapmike/Reddit.com

11. Al Capone and His Associates Walking Confidently Out of Court, 1931

A group of men in suits and hats walk together in what appears to be a train station or industrial setting. The central figures look serious, dressed in dark overcoats, while others surround them, also wearing hats and coats.
StickyMicky13/Reddit.com

12. Mobster Mickey Cohen Inspects the Damage After a Bomb Went Off in His Brentwood Home, February 1950

A man in a bathrobe looks at a closet in a heavily damaged room with debris, broken wood, and a torn ceiling. Another person stands in the background. The scene appears to be indoors, possibly after an explosion or disaster.
dear_patrick/Reddit.com

13. Mobster Joe Gallo Testifies in Court While Wearing Ray-Bans, 1950s

A man wearing dark sunglasses and a black outfit sits at a table speaking into a microphone, with glasses of water in front of him. The background is out of focus, showing other people and a large chandelier.
urinetroublee/Reddit.com

14. Charlie Birger and His Gang of Bootleggers Looking Mighty Intimidating During Prohibition in Illinois, 1927

Black-and-white photo of 16 men posing with guns in front of a log cabin porch. Text above reads, "Birger and His Gang." Some men are standing, others sit or kneel; all face the camera.
FawmahRhoDyelindah/Reddit.com

15. Mugshot of Chicago Gangster George ‘Bugs’ Moran, Al Capone’s Rival, in Dayton, Ohio, 1946

Black and white mugshot of a man in a suit and tie, shown in both profile and front views. He has wavy dark hair, and the sign reads "Dayton Ohio 20774, 7-13-46.
mafia/Reddit.com

16. Mob Boss Sam Giancana Arrives at Federal Court in Chicago, 1965

A man in a suit, dark sunglasses, and a hat walks confidently down a hallway, flanked by men in suits. Photographers with cameras and flashes surround him, capturing the moment. The scene is in black and white.
jmtheo21/Reddit.com

17. ‘Wiseguys (Mafia Men) Eating at a Restaurant in New York, 1966’

Seven men in suits sit around a table set with food, drinks, and wine bottles, engaged in conversation during a formal meal in a black-and-white photograph.
Remarkable_Put_7952/Reddit.com

18. The Infamous Kray Twins (Ronnie and Reggie), Known for Racketeering, Armed Robbery, and Organized Crime in London, 1965

Two men in formal attire stand indoors, both holding teacups and saucers. One wears a suit and tie; the other, with glasses and suspenders, has his shirt partly unbuttoned. They look ahead with surprised expressions.
mantoine/Reddit.com

19. Mugshot of Charles ‘Lucky’ Luciano, Considered the ‘Father of Modern Organized Crime’ in the US, 1936

Black-and-white mugshot showing a man in a suit and tie, photographed from the side and front. He holds a placard that reads “N.Y.C. POLICE 72321 4/18/36.”
Mikey_Tuna/Reddit.com

20. Men Line Up Outside a Soup Kitchen Sponsored by Al Capone During the Great Depression in Chicago, 1931

A long line of men in coats and hats wait outside a building with a sign reading "Free Coffee & Doughnuts for the Unemployed." The scene appears to be from the Great Depression era.
Cosmicreature/Reddit.com

21. Infamous Colombian Drug Lord Pablo Escobar (Right) Poses as a Gangster With His Cousin Gustavo, 1980s

Two men in vintage suits and hats pose with stern expressions; one holds a Tommy gun, the other holds a bottle of Jack Daniel's whiskey and shows a middle finger. The black-and-white photo has an old, grainy effect.
Slejb/Reddit.com

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Left: An older man in a hat and plaid shirt sits with his arms crossed, smiling as a microphone is held near him. Right: Several men in suits sit at a table, one wearing sunglasses, during a formal hearing or meeting.
reddcaesarr/Reddit.com / Bettmann/Getty Images
Author
Alina Wang

From Queens, New York, Alina has a Bachelors degree in Corporate Communications from CUNY Baruch and enjoys writing and creating content on a variety of topics, including lifestyle, politics, and, of course, wealth trends. Find her on X @atlasseventeen