This is exactly what it sounds like.
These are our top 8 picks for Chicago’s hottest gangsters, mobsters, bank robbers and, yes, even corrupt politicians. If you want, you can find out more about them using a free people finder tool.
8. Rod Blagojevich
Best Known For: Perpetuating the stereotype that Chicagoans know, and very rarely love – that we like to play dirty.
Blagojevich, who served as Illinois’s governor from 2003 to 2009, was impeached in 2011 and imprisoned for attempting to “auction off” the empty Illinois Senate seat following Obama’s Presidential election in 2008. Some of his other charges included: racketeering conspiracy, wire fraud, extortion, regular conspiracy, attempted extortion and making false statements to federal agents. He is currently serving a 14-year prison term.
Plus, if we’re talkin’ hotness here, Blago was a former boxer so, ya know that counts for at least little something.
7. Gertrude ‘Billie’ Murphy
Best Known For: Making a love triangle deadly.
6. Vincent “The Schemer” Drucci
Best Known For: Creatively evading the po-po.
The Schemer first graced Chicago headlines after jumping into the Chicago River off of the Michigan Avenue Bridge to escape police during a car chase. He was most notably known for his wild schemes like traveling to London to steal the Crown Jewels. He was also a member, and later the leader, of Chicago’s North Side Gang – Al Capone’s well-known rival. His main gimmick: he dressed up as a priest and tormented local residents.
He was eventually killed by police in 1927, putting a definitive stop to his inventive criminal antics.
5. Rose Laws aka Miss. Rose
Best Known For: Hanging out with the wealthiest – and at times skeeziest – of Chicago gentlemen.
The Madam of the Gold Coast provided female escorts for Chicago’s elite for a little over 30 years. Clients included politicians, celebrities, athletes, lawmen and the wealthy and powerful. Now 75, she says she documented over 5,000 clients which are scribed in her famous little black book.
If you are interested in more of her exploits you can find her book here.
4. Hymie Weiss
Best Known For: Facing off with Al Capone.
Despite an admittedly un-intimidating sounding name, Hymie Weiss is a vicious mob boss in Chicago’s golden age of gangsters. The head of the North Side Gang – Capone’s sworn rival – this mobster was said to be the one man Al Capone feared. Now that’s what we call hot.
2. & 3. Beulah Annan and Belva Gaertner
Best Known For: “And all that Jazz”
If you haven’t heard of the musical Chicago by now, well get yourself acquainted because, these girls were the inspiration behind it. Belva (bottom) was the model for Velma Kelley and Beulah (top) for Roxy Hart.
Contrary to what the award-winning production might suggest, Belva was not, in fact, arrested for killing her sister and husband. Instead, this gangster in Chicago was charged with the murder of her lover who she shot while he was in his car.
Much like Roxy, however, Beulah was indeed charged with shooting her lover in her apartment. While her motives are still inconclusive, it was widely believed she killed him because he failed on his promise to make her a famous jazz musician. She – again, like Roxy – also changed her story multiple times and coined the famous phrase “we both reached for the gun” as well as faked her pregnancy during her trial.
These two mobsters in Chicago met on “Murderess’ Row” in Cook County Jail where they opened a beauty salon where they helped fellow female prisoners dress for their trials.
1. John Dillinger
Best Known For: Escaping jail-time (literally), two-dozen-plus bank robberies and telling the police to “eat my dust.”
Those baby blues, that dark hair, and sly smirk. What is not to love? I mean, besides the obvious affiliation for crime.
The Indiana native and notorious bank robber was not only known for his wicked charm and organized crime skills but his smolderingly good looks. While the majority of his crimes took place in every other Midwestern state except for Illinois; he has, to this day, been widely considered a Chicago mobster.
After escaping from prison in 1934 he hid out in Chicago’s Uptown neighborhood with the help of girlfriend Mary Evelyn “Billie” Frechette. After being killed by police in front of Lincoln Park’s Biograph Theater, the body of this ganger in Chicago that was displayed by the CPD attracted over 15,000 visitors… because you know, that was normal.
As an added point of evidence, Dillinger was played by Johnny Depp in Public Enemies, which has gotta say something.
Honorable Mention: Al Capone – While he may be Chicago’s most famous and notorious… I’m sorry Al Capone fan’s, but his syphilitic brain, extreme paranoia, and deteriorating health did not make for a sexy addition.
Featured Image Credit: Again, literally, the FBI.
