During the Great Depression gangsters were glorified as celebrities for their illegal deeds and flamboyant lives. From bootleggers to bank robbers, we count down the baddest boys and girls in American history.
George Barnes Jr., also known as Machine Gun Kelly (1990-1954), was a formidable gangster during the Prohibition famous for his penchant towards Thompson submachine guns. His crimes included bootlegging, armed robbery and the kidnapping of an oil tycoon in 1933. Not to be confused with Machine Gun Jack.
9. Legs Diamond
Jack “Legs” Diamond (1897-1931), was a bootlegger in Philadelphia and New York during the Prohibition. The nickname “Legs” refers to his smooth dancing skills and nimbleness in escaping his enemies. He was also dubbed “Gentleman Jack” for his womanising habits.
George R.’Machine-Gun’ Kelly by American Photographer, c.1930; Peter Newark American Pictures / Bridgeman Images; Jack ‘Legs’ Diamond (1896-1931) by American Photographer; Peter Newark American Pictures / Bridgeman Images
The Barkers were a whole family of bad eggs and one of the longest-lived criminal gangs during the Depression. Rumoured to be headed by the three Barker brothers’ mother, Kate, they ruthlessly committed bank robberies and kidnappings between 1931-1934. The apple evidently never rots far from the tree.
L-R: ‘Ma’ Barker, ‘Doc’ Barker, ‘Old Creepy’ Barker; Peter Newark American Pictures / Bridgeman Images
7. Bugsy Siegel
Blue-eyed, handsome and charismatic, racketeer Benjamin “Bugsy” Siegel (1906-1947) was a poster boy for the crime ring in New York. He was closely associated with fellow Jewish mobster Meyer Lansky and was a boyhood friend of Al Capone. He was assassinated 1947 at the house of his lover, Virginia Hill, a prominent gangster’s moll.
6. Meyer Lansky
Born Meyer Suchowljansky in Belarus, Lansky (1902-1983) was instrumental in developing the National Crime Syndicate in the US alongside his associate Lucky Luciano. He built a gambling empire that stretched to Las Vegas, Cuba, The Bahamas and London, while exerting his influence over both the Jewish mob and Italian mafia.
Benjamin ‘Bugsy’ Siegel by American Photographer; Peter Newark American Pictures / Bridgeman Images; Meyer Lansky by American Photographer; Peter Newark American Pictures / Bridgeman Images
It is not known how Charles “Lucky” Luciano (born Salvatore Lucania) received his name, but undoubtedly he had some close shaves during his career as a bootlegger and crime boss. Often considered the father of modern organised crime in the US – and the most powerful Amercian Mafia boss of all time – he and his childhood friend Meyer Lansky were instrumental in developing the National Crime Syndicate.
4. Carlo Gambino
Carlo Gambino (1902-1976) was the original boss of the Gambino crime family, one of five Italian-American Mafia families in New York who have dominated the United States since 1931. His illegal dealings included racketeering, gambling, loansharking, laundering, prostitution, fraud and theft to name but a few. Unlike other celebrity gangsters, like the flamboyant Al Capone, Gambino was known for being secretive and kept a low profile.
John Dillinger (1903-1934) was one of the most notorious of all outlaws during the Depression-era heydays, not least because his exploits and bravado were colourfully exaggerated by the media. Between his release from prison in 1933 and his death in 1934, he robbed two dozen banks and four police stations and evaded the police in four different states. 21st July 2019 sees the 85th anniversary of his death.
Charles ‘Lucky’ Luciano, 1936 by American Photographer; Peter Newark American Pictures / Bridgeman Images; John Dillinger, 1934 by American Photographer; Peter Newark American Pictures / Bridgeman Images
Living fast and dying young, Bonnie Parker (1910 – 1934) and Clyde Barrow (1909 – 1934) go down in history as the star-crossed lovers in outlaw history. As with most boy-meets-girl tales, the couple met through a friend and fell in love at first sight, going on to rob banks, stores, gas stations and kill at least nine people before being gunned down by the police at the ages of 24 and 25 respectively.
Bonnie Parker posing ‘tough’ with a gun and cigar, c.1934 by American Photographer; Peter Newark American Pictures / Bridgeman Images; Clyde Barrow, 1934 by Bonnie Parker (1910-34); Peter Newark American Pictures / Bridgeman Images
1. Al Capone
The face of the Prohibition, Alphonse “Al” Capone (1899 – 1947) was the undisputed crime boss of Chicago. Running prostitution, gambling and bootlegging rings, stories of his wealth and corruption made him a controversial national celebrity. Despite his violent nature, he was also known for his intelligence and larger-than-life personality; his generous donations to charity earned him the title “modern Robin Hood”.
Al Capone (1899-1947) fishing on his yacht by American Photographer; Archives Charmet / Bridgeman Images; Miami Police Department mug shot of Al Capone, 1930 by . ; HistoryMiami, Florida, USA / Bridgeman Images
Honourable Mention – Frank Sinatra
Better known for his singing, Francis “Frank” Sinatra (1915 – 1998) was strongly associated with, but never proven to be a part of, organised crime. He did, however, have brushes with the law and socialised with gangsters including Lucky Luciano and Carlo Gambino. The FBI kept an eye on ‘Ole Blue Eyes for almost five decades, with records amounting to a rumoured 2,4000+ pages.
Original mugshot of Frank Sinatra, 1938 by American Photographer; © Christie’s Images / Bridgeman Images
Find out more
Peter Newark American Pictures: browse a fantastic archive of movie stills, police mugshots, wanted posters and much more.
Prohibition: see more images from this era of fast and dangerous living.
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