From Al Capone to John Dillinger, the Windy City has been the backdrop for some of America’s most notorious characters. The tales of these famous Chicago mobsters and gangsters have intrigued people for decades, leading to the retelling of their stories through countless books, movies, and documentaries, as well as guided tours on the streets these gangsters once ruled.
Here are some of Chicago’s most infamous gangsters:
Al Capone - “Scarface”
Al Capone is the most famous gangster from the 20th century. He was born in New York City’s Brooklyn borough on January 17, 1899. Capone became infamous, though never indicted, for his alleged role in the St. Valentine’s Day Massacre on February 14, 1929. A fun fact about Al Capone is that he is one of 9 children. Al had 7 brothers and one sister. Al Capone rose to power as the leader of the South Side Gang, also known as the Capone Gang or more contemporarily known as The Outfit. Al was eventually convicted for federal income tax evasion. While imprisoned in Alcatraz, he was treated for syphilis, and subsequently released from prison due to his mental state after medical treatments. Al Capone ultimately died of a heart attack on January 25, 1947, while getting out of the shower at his palatial estate in Miami, FL.
John Dillinger - "Public Enemy No. 1"
Second in infamy to Al Capone, John Dillinger was the most notorious Depression Era bank robber. He was an A-list movie star gangster of his time. Dillinger was said to “rob banks, not people,” which was very popular during The Great Depression. Dillinger’s 18-month crime spree was from 1933 to 1934, in which he was arrested several times and escaped from 3 different jails. After watching the gangster film Manhattan Melodrama at the air-conditioned Biograph Theater on a hot summer night on July 22, 1934, Dillinger walked his last steps.
Vincenzo Colosimo - “Big Jim”
“Big Jim” Colosimo was known as the first Vice Lord of Chicago. He was born February 18, 1878, in Colosimi, Calabria, Italy. Colosimo started the South Side Gang aka the modern-day Outfit. Big Jim was known as the “Patron Saint” of the Capone Syndicate. Big Jim was also known as Diamond Jim because he loved to wear white clothes and diamonds. Jim was also known to carry loose diamonds in his pockets, kind of like a fidget toy. He made his fortune in the vice business, including prostitution and extortion, but he had no interest in bootlegging, the enterprise that would later lead to the Chicago beer wars. This was unfortunately his downfall, as his own gang had other ideas. The first Vice Lord of Chicago was found dead in his own café after being gunned down and shot in the head on May 11, 1920.
Johnny Torrio - “The Fox”
Johnny Torrio was the second in command or underboss to Big Jim Colosimo and the speculated cause of Big Jim’s demise. Torrio rose to power during the beginning of Prohibition and a major player in the beer wars of Chicago gangland in the Roaring 20s. Jonny Torrio was born on January 20, 1882, in Italy. Torrio had many nicknames including: The Fox, The Brain, Papa Johnny, Terrible Johnny, The Immune, etc. After an assassination attempt in 1925, Torrio handed over the helm of the Chicago gang to Al Capone. Johnny Torrio left Chicago for New York and became a consultant for organized crime. Torrio suffered a heart attack and then died on April 16, 1957.
Frank Nitti - “The Enforcer”
Frank “The Enforcer” Nitti took over as the crime boss of the South Side gang after Al Capone was imprisoned in Alcatraz. Nitti was born in Italy on January 27, 1886. He was most famously known for his largest scheme, which involved attempting to extort 1 million dollars from major Hollywood production studios. Throughout his varied career as the enforcer, Nitti served time in prison and developed a fear of small confinement, also known as claustrophobia. Nitti’s crippling fear of returning to prison and looming grand jury appearance weighed heavily on his shoulders. Frank Nitti shot and killed himself on March 19, 1943.
Murray Humphreys - “The Camel”
Murray “The Camel” Humphreys was one of the smartest and well-placed members the South Side Gang among Al Capone, Johnny Torrio and others. Humphreys was born in Chicago on April 20, 1899. Murray Humphreys was known to use his head as a financial fixer, political liaison and chief strategist. Humphrey’s claim to fame was that he succeeded Al Capone as Public Enemy #1 after Capone went to Alcatraz. Humphreys died of a heart attack while in his home on November 23, 1965.
George Moran - “Bugs”
George “Bugs” Moran was well known as the man who got away from the St. Valentine’s Day Massacre. George was born in Minnesota on August 21, 1893. Moran rose through the ranks and eventually became boss of the North Side Gang during Prohibition in Chicago. On February 14, 1929, the date of the St. Valentine’s Day Massacre, George wanted to look good for his sweetheart, so he got a haircut and was late to a meeting at a Northside distribution site for the North Side Gang. This haircut ultimately saved his life, and Moran would continue his gangster career for many years to come. George Moran ultimately died due to lung disease on February 25, 1957.
These are only a few of the high-profile Chicago gangsters who gained a reputation for lawlessness during The Great Depression and Prohibition. While times have changed, these infamous gangsters provide an interesting glimpse into Chicago’s history of true crime, lawlessness, and vices.