Of all the great Chicago swindlers - and my goodness, we've had a few of those - it's possible that none was quite so good at what he did as Yellow Kid Weil, the greatest con man of the 20th century.
Perhaps nothing better illustrates his abilities than the stories of him appearing at the Dil Pickle Club back in the 1920s. The Dil Pickle was one of Chicago's most famous open forums - a bar (well, not a bar - this was one of the few places during prohibition where you COULDN'T get a drink, as no one there could afford the necessary bribes, and, being packed with anarchists commies, they had enough to worry about without breaking one more law) where people would gather to discuss events of the day, listen to "anyone who was a nut about something" make a speech. Captain Streeter spoke there. So did Jane Addams, Clarence Darrow, and most every other major thinker of the day. Often, after the discussion, Carl Sandburg would play a few folk songs (long before folk-singers became a fixture of coffee shops).
The infamous Yellow Kid spoke there on more than one occasion, but his speeches were not so much speeches as demonstrations. He would arrive several hours late, and, instead of giving a speech, proceed to take the audience for twenty bucks. The audience KNEW that he was a con man, and probably barely had twenty bucks between them, but the Yellow Kid somehow managed to con them out of it anyway.
The Yellow Kid died in the 1970s at the age of 100, having stolen something like eight million bucks over the years. While the stories that went around that he never stole from an honest man were probably nonsense, he insisted that most of them were, in fact, people trying to get something for nothing who bought into his many schemes. "Every one of them," he said, "had larceny in his heart."