Who were the great Chicago con men?

July 19, 2017 12:24 PM

I started reading about The Yellow Kid and some of his stories and wanted to know who else fit the bill for great Confidence Men of Chicago.
posted by rileyray3000 to Society & Culture (6 answers total)

Leo Koretz was a Chicago based con-man in the early 1900's. He ran a huge Ponzi scheme based on a land fraud and a fake oil and timber company in South America. Led the cops on a long, cross-country chase and was by all accounts totally charming. He later died in prison, in a "suicide by diabetes" anti-climax.
posted by cosmicbandito at 1:03 PM on July 19, 2017

Possibly Fred and Charley Gondorff. They provided the inspiration for the movie The Sting, which is set in Chicago.

You can read about the Gondorff brothers in The Big Con: The Story of the Confidence Man.
posted by Winnie the Proust at 1:05 PM on July 19, 2017

Nope. According to some reviews of The Big Con, the Gondorffs were from New York. Sorry for the false lead.
posted by Winnie the Proust at 1:12 PM on July 19, 2017

I'm researching a book about a con man who had an international reach from about 1917 to 1949. Though he didn't limit himself to Chicago, he memorably fleeced several Chicagoans. (And was a self-professed fan of Yellow Kid Weil's.) His M.O. was to meet, court, charm, and marry a wealthy widow or (forgive me) spinster. He'd then disappear with their money/furs/jewels before the honeymoon and move on to the next one. He married upwards of 30 women -- sometimes marrying the next less than a week after marrying the last -- and stole from countless others who didn't fall for the marriage gag. I have a list of over 100 aliases that he used.

He was tried in Chicago in 1949 for the final time and died in prison in Illinois. During his "career," he stole the equivalent of millions of dollars in today's money.

Because no one has written about him to date, I don't want to share his name here. (Fear of being scooped!) I have a ton of newspaper articles about him, though, and would be happy to send you some of them. Send me a MeMail if you want to know more.
posted by mudpuppie at 3:24 PM on July 19, 2017

H. H. Holmes was a successful con man, though he's more infamous for the serial killing..
posted by Nerd of the North at 3:27 PM on July 19, 2017

Joseph Weil?

As a Chicagoan by birth, I'm certain there are lots. But I'm drawing a blank.
posted by persona au gratin at 3:45 AM on July 20, 2017