Fats Waller was kidnapped in Chicago leaving a performance in 1926. Four men bundled him into a car and took him to the Hawthorne Inn, owned by Al Capone. Waller was ordered inside the building, and found a party in full swing. Gun to his back, he was pushed towards a piano, and told to play. A terrified Waller realized he was the “surprise guest” at Capone’s birthday party, and took comfort that the gangsters did not intend to kill him. According to rumor, Waller played for three days. When he left the Hawthorne Inn, he was very drunk, extremely tired, and had earned thousands of dollars in cash from Capone and other party-goers as tips.


When Al Capone tried to buy the Chicago Cubs,

Al Capone was a big fan of baseball, especially the Chicago Cubs. But of course, it drove Capone crazy to no end that the Cubs couldn’t win a World Series supposedly because of the “curse of the billy goat”. Capone didn’t blame the Cubs lackluster performance on superstitions and curses, but a rather a shortcoming in management.  On a number of occasions he commented that with his experience he could run the Cubs much better than current owner William Wrigley. 

In the late 1920′s, Capone decided to literally put his money where his mouth was and attempt to buy the Chicago Cubs.  To head his team, Capone wanted his favorite player, Babe Ruth, as a player manager.  In fact, Capone organized an all expenses paid trip to Cuba in 1929 with Ruth in order to negotiate a deal.  Ruth was enthusiastic about the plan, having always wanted a management position.  The two sealed the deal by autographing this baseball, which sold for $61,863 in 2013.

Unfortunately for Capone, his plans were ruined by three major problems. First New York Yankees owner Col. Jacob Ruppert refused to sell Babe Ruth’s contract despite being offered $500,000 in cash. Second, William Wrigley likewise refused to sell the Cubs.  Finally, and most importantly, Capone was convicted on charges of tax evasion in 1931 and sentenced to 11 years in prison in 1932. Alas it was not to be.