Chicago January 06, 2018
The 9 Most Infamous Outlaws To Ever Come Out Of Chicago
Chicago is well-known for its infamous outlaws. From gangsters to psychopaths, we’ve had our fair share of terror mongers in this city. Take a trip with us through history to revisit nine of the worst criminals to ever pass through here.
This list goes all the way back to American’s first serial killer! Keep scrolling for more details.
1. H.H. Holmes (1861-1896)
Known as America's first serial killer, this dastardly doctor kicked off his murderous spree in Chicago. He built a hotel, today known as "Murder Castle," prior to the World's Columbian Fair, with different parts constructed at different times. He was a shady character who never fully disclosed the purposes for the add-ons to his hotel, and he used multiple contractors (whom he never paid) to keep it all a secret. Of course, the worst of his crimes were the murders of
at least 27 people (some believe the real number is in the hundreds), mostly women whom he would lure to his hotel, torture, then execute.
2. Al Capone (1899-1947)
Also known as "Scarface," this is one of the most infamous outlaws associated with Chicago. He was an American gangster who grew up in Brooklyn before moving to Chicago and working as a bouncer. For seven years, he reigned as the number one crime boss in the city, making millions off illegal alcohol sales during Prohibition.
3 & 4. Nathan Leopold (1904-1971) and Richard Loeb (1905-1936)
These two men acted together in 1924 to kidnap and murder a 14-year-old boy, believing they would get away with it due to their privileged social stature and self-determined intellectual superiority. They were students at the University of Chicago who were (obviously) not as smart as they thought they were. Both Leopold and Loeb were arrested and thrown in prison, where Loeb was murdered by other inmates and Leopold lived to old age, eventually dying of a heart attack.
5. John Dillinger (1903-1934)
This well-known outlaw was a Depression-era gangster who robbed 24 banks and escaped from prison twice. His only convicted homicide was the murder of a police officer, though there were likely many more. His time was up in 1934, when his girlfriend exposed his whereabouts (at Biograph Theatre) to the cops and he was shot down as he attempted to flee.
6. Richard Speck (1941-1991)
This atrocious Illinois resident kidnapped eight student nurses from their South Chicago college dorm in 1966, submitting them to torture, rape, and murder. Though originally sentenced to death, his case was overturned, and he was instead given life in prison, where he died of a heart attack at the age of 49.
7. John Wayne Gacy (1942-1994)
Known as "The Killer Clown" due to his job as a party clown, this man sexually assaulted and murdered more than 30 teenagers and young men in the 1970s. The bodies were found around his property and in the Des Plaines River. After his capture, he spent 14 years on death row before his execution in 1994 by lethal injection. His crimes were so gruesome that they inspired the Missing Child Recovery Act of 1984, which has since evolved into the AMBER Alert system used for child abductions today.
8. Ted Kaczynski (1942-present)
There may very well be a fine line between genius and insanity. Known as the "Unabomber," Kaczynski is a domestic terrorist who mailed bombs to people involved in modern technology, killing three people and injuring 23 others. He started out as a mathematician who attended Harvard, but gave up that life to become a survivalist in the wild before starting his homemade bomb campaign. He is still alive and in prison, serving eight consecutive life sentences without the possibility of parole.
9. Rod Blagojevich (1956-present)
Though his crimes were not as serious as murder, this is one of the most corrupt politicians to ever come out of Chicago, and is one of our most infamous outlaws in modern history. He was sentenced in 2011 to 14 years in prison for corruption charges for soliciting bribes for political positions, including Barack Obama's vacant Senate seat after he was elected President.
What other infamous outlaws do you remember from Chicago’s past? Share your stories with us in the comments below!
If you love learning about Chicago’s history, check out these
11 things that our city was first to unveil.