The 9 Most Infamous Outlaws To Ever Come Out Of Chicago

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.

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.

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.

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.

Though his crimes were not as serious as murder, this is one of the most corrupt politicians to ever come out of Chicago, and he is one of the 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.