In the fall of 1926, the best friend of Chicago gangsters returned to politics and got his name added to the Republican mayoral primary ballot. William “Big Bill” Thompson was back from political exile – he just couldn’t stay away.
In early July, he sailed his yacht down the Chicago River and into Lake Michigan, carrying an motley crew of politicians, businessmen, beer-swilling clowns, assorted cronies, and a gangster or two. They were cheered on by thousands of people who lined the shoreline. The man was a walking punchline, but people loved him.
He’d spent the last year or so rebuilding his political capital, knowing that Chicago was not a city that wanted reform as badly as the current mayor wanted to offer it. Al Capone was so enthused about the corrupt former mayor's return that he contributed $250,000 to Thompson’s campaign fund and introduced every form of bribery and terrorism imaginable on the man’s behalf.
It was also during this campaign that Capone was credited with the Chicago’s most famous political slogan and one that’s still around to this day:
“Vote early and vote often.”