Top 5 Chicago Criminals of All-Time

Top 5 Chicago Criminals of All-Time

Chicago, the beloved second city, has been second to perhaps only NYC in high-profile criminals over the years. This list is obviously quite condensed, but these 5 figures span different crimes and times. All house hold names, they've either begun, ended, or lived their life of crime in Chicago.

5. Ted Kacyznski

Better known as the "Unabomber", this tasty Chicago relic was born in Chicago in 1942, where he immediately was on track to become a great mathematician. He was accepted to Harvard at age 16, obtained a Ph.D. in Mathematics from the University of Michigan, and was an assistant professor at Cal-Berkeley by the age of 25.

But then, he found a quaint cabin in the woods, where he started learning survival skills, and eventually bombing skills in reaction to the deforestation he witnessed near his home. He sent out 16 bombs to locations across the country, which initiated one of the costliest FBI investigations in history. The "Unabomber" name stands for "university and airline bomber".

He's now at a quaint prison, no doubt learning evasive rape-avoidance skills.
4. John Wayne Gacy

Some people are just born with an appetite for bad things. Gacy is Chicago's worst serial killer of all-time, murdering and raping AT LEAST 33 teenage boys in the Chicago area.

Gacy was known as the "killer clown", because of his amiable personality, helping out with children's fundraisers dressed as a clown. He was also a successful businessman in Waterloo, Iowa, working for the Nunn-Bush Shoe Company, and later managing three Kentucky Fried Chicken restaurants.

If you want to read a great book about Gacy, read The Last Victim: essentially a story about a boy who infiltrates Gacy's trust and may be a reason Gacy ended up getting the gas chamber.

If he had it his way, he'd be at a big Child's fundraiser in the sky.

3. Rod Blagojevich

Ah, Rod. Only the 4th of the last 8 Illinois Governors to serve time behind bars. And its not necessarily the crimes he's committed, but the flare with which he has maintained his innocence that we must include him in the list.

In 2008, Rod received an 'excellent' approval rating by exactly zero percent of Illinois voters. Shortley thereafter, Rod was booked and on his way to jail for corruption charges, specifically his 'pay to play' scheme to fill Obama's vacant senate spot.

What his money has actually bought him is an opportunity to wash dishes and teach shakespeare in a Colorado penitentiary. Fortunately, he's still able to maintain his voluptuous head of hair.

2. John Dillinger

Now for the 'cool' criminals. Dillinger was a depression-era gangster and bank robber, who was notorious for getting away with crimes and not harming those he stole from. Although, he was held responsible for one murder during a bank robbery, but most people believed it was not Dillinger that fired the shot.

After being wounded while on the run across 4 states, Dillinger was located at the Biograph Theater in Chicago. Dillinger, while attempting to escape, pulled his gun on police and was shot and killed.

He is survived by family descendants and Johnny Depp.

Al Capone
1. Al Capone

The name alone says Chi-town. During the prohibition-era in Chicago, Al Capone owned the town.

Born in an Italian borough in New York City, Capone moved to Chicago chasing dreams of becoming 'the guy', and fell nothing short of that. His booze trade, along with buying off political figures in Chicago, earned him a highly public profile, even stardom.

However, the Saint Valentine's Day Massacre in 1929 in present day Lincoln Park, which Capone was linked to, ruined his reputation, and he was soon after arrested for tax evasion. Sent to Alcatraz, Capone began deteriorating mentally and physically, eventually dying of a stroke in 1947.

Known as the "modern-day Robin Hood", Capone is a good reminder that sometimes when you take something away that everyone wants, it leads to much more crime.



Leave a comment
  • Interesting collection of dregs.

    The Roddster is among the top 5? I'd accept that if it were the dumbest bad guys.

    Ted K., by the way, lived in Evergreen Park, but his house is only a mile or so from Chicago, so he is honorary Chicago. He remains the most famous graduate of Evergreen Park Community High School.

  • Thats great,

    Yeah, i felt the need to throw a little Rod jab, just because I find him so hilarious.

    Ted K, when are they going to make a severely dark movie about him, maybe with Kevin Spacey or Robert Deniro as the lead role?

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