Rod Blagojevich. Born in Chicago, Rod Blagojevich is one of the most famous criminals amongst America’s politicians. He is currently serving a 14 year prison sentence for corruption because he tried to auction off Barrack Obama’s vacated Senate seat.
John Dillinger. One of the most famous bank robbers in US history who became a heroic outlaw for the people during the depression era. His crime career began after received a harsh sentence, 10 to 20 years, for robbing a store of $50 when he was young. It was a shock because he pleaded guilty and expected a light sentence. While in prison, Dillinger promised to be the worst criminal he could be and befriended veteran bank robbers to learn the trade. For Dillinger, prison became bank robbing university.
He escaped capture twice with the help of his gang, the Dillinger gang, and Dillinger even robbed 4 police stations to acquire more guns and ammunition. When in hiding he often came to Chicago to disappear but still loved attending Chicago Cubs games. At the time he was more a more notorious criminal than Baby Face Nelson and Bonnie & Clyde.
Lawmen finally caught up to Dillinger, after 2 dozen armed robberies, at Biograph Theater in Lincoln Park, Chicago. Fleeing, he was hit 3 times from behind by several gunmen and died instantly. Rumors say several people in the crowd dipped their handkerchiefs in his pool of blood on the ground as a souvenir of the incident.
Ted Kacyznski. The famous domestic terrorist known as the “Unabomber”, Ted Kacyznski was born in the Chicago subarb Evergreen Park, and began life as a child prodigy in mathematics. He attended Harvard at 16 for his undergraduate degree and moved on to obtain a PhD in mathematics at the University of Michigan. In 1971 he moved to the wilderness in a remote cabin built with his own hands in Lincoln, Montana to learn survivalist skills.
While in his cabin in Lincoln, he became disillusioned with man destroying nature and decided to build bombs and mail them to various targets, mostly airlines and universities from 1978 to 1995. Throughout his terror spree he sent a total of 16 bombs injuring several people and killing 3. He was finally apprehended in 1996 by the FBI and is currently spending a life sentence in the supermax prison called ADX Florence (Administrative Maximum Facility) in Florence, Colorado.
Al Capone. No one is more legendary in the US-Sicilian Mafia than Chicago Outfit leader Al Capone. He was born in NYC but moved to Chicago in his 20s. He made his fortune in the prohibition era bootlegging (smuggling) and selling illegal booze and prostitution. His Chicago Outfit was the top criminal organization in Chicago and made up to $100 million annually. He was the first gangster to become a celebrity with the public and often donated money and opened soup kitchens to keep himself in good standing with Chicago citizens. He was never directly connected to crimes and used bribery and intimidation to keep himself out of prison as a mob boss.