The top five gangsters in Chicago history

Chicago’s gangsters of the 1920s and 30s were some of the most famous Chicagoans of all time. They were the baddest of the bad guys, yet the champions of the people. Some of the more notorious Chicago gangsters lived on through being portrayed in film, and most often they were the protagonist (or, the anti-hero).

But who were these heavy hitters? What did they do, what were they known for? Here’s a look at some of the more notorious Chicago gangsters.

Gangsters of Chicago

Al Capone. The most famous (or infamous) Chicago gangster. Capone was born to a poor Italian immigrant family in 1899. Capone became the protégé of Johnny Torrio, leader of the Five Points Gang. Torrio was bootlegger, and his gang made a fortune during Prohibition. After Torrio retired in 1925, Capone took over and became the major crime boss of Chicago, running gambling, prostitution, and bootlegging rackets and expanding his turf by the killing rivals. Experts say that Capone was worth $100 million in 1927. Capone’s most famous action is the St. Valentine's Day Massacre, where Capone hired shooters to gun down Bugs Moran’s rival gang. Capone began to meet his demise in 1931, where he was sent to prison for, of all things, income tax evasion. His health rapidly deteriorated, and Capone died in 1947.

Dion O’Banion. Born in the Chicago area (there are conflicting reports as to where) in 1892, O’Banion (whose real name was Dean) grew up in Chicago and became a singing waiter at McGovern’s Saloon and Cabaret, a mobster hangout. Fellow Irish-American Gene Geary, a notorious gunman, took O’Banion under his wing and taught him gunplay and racketeering. Soon enough, O’Banion became the leader of the North Side Gang in Chicago during the bootlegging heyday of the 1920s. His chief rival was Johnny Torrio (Capone’s mentor), and after a perceived double-cross at O’Banion’s flower shop (a guise for his bootlegging operation), Torrio was sent to jail. Capone dispatched three underlings to murder O’Banion at that same shop in 1924.

Bugs Moran. Like most gangsters, Moran got started with crime early. After moving to Chicago at 19, Moran was jailed three times at the age of 20. Moran quickly became pals with O’Banion and became leader of the North Side Gang in 1927 after the murders of O’Banion and a few other leaders. Moran was known as being gung-ho, not afraid of being the leader in a bloody shoot-out. And since Moran was so colorful and humorous with the press, peppering their stories with insults of Capone, the feud with his chief rival escalated. This led to the St. Valentine’s Day Massacre, where many of Moran’s top men (but not Moran himself) were killed. Moran’s power began to wane in the 1930s, and after being in and out of prison.

Tony Accardo. A hitman for Capone, Accardo is believed to be involved with the St. Valentine’s Day Massacre and the assassinations of gang bosses Frankie Yale and Hymie Weiss. Accardo grew up on the West Side of Chicago in the 1910s, and when he was around 18 he met up with Capone. Accardo did odd jobs for Capone, delivering moonshine and committing muggings, pick pocketing, burglary, car theft, armed robbery and assault, later becoming a killer. After Capone was sent to jail, Accardo became a mob boss himself, and aroused the suspicion of the IRS due to all the money Accardo’s outfit brought in. Surprisingly, Accardo denied all mob connections to the day he died (wire taps suggest otherwise), and Accardo died of natural causes in 1992.

John Dillinger. Not a gangster in the Capone/O’Banion sense, Dillinger a prolific bank robber with ties to Chicago. Dillinger got started with petty crimes, like stealing chickens. He tried his first robbery at 21; it did not go well – he was sentenced to 10 to 20 years in prison. After Dillinger was paroled in 1933, he was again jailed after a bank robbery, but was broken out of jail later that same year. Dillinger and his accomplices robbed banks, and they did it with style. They would use ruses and phony stories like they were bank alarm salesmen or film directors looking for locations for a bank robbery scene. Dillinger and his men roamed the Midwest, stealing more than $300,000 from dozens of banks. Dillinger’s main hideout was in Chicago, and reports say that only weeks before his death he attended Chicago Cubs games. After a set-up, Dillinger was killed by the FBI at the Biograph Theater in Chicago in July of 1934.