When Prohibition arrived in Chicago, one club managed to thrive despite the alcohol ban. Jazz fans flocked to the Green Mill on the north side of Chicago. They hid their bootleg whiskey in hip flasks, and enjoyed the incredible headliners. The club helped to launch the careers of singers like Helen Morgan, Anita O’Day, and Billie Holliday.

In the middle 1920s, the club was leased to Al Capone’s Outfit. Capone was seen there often, despite the fact that it was in the middle of his arch rival's territory. But it's not Al Capone that attracts historians to the Green Mill. It’s the legend of Jack McGurn, who managed the club for Capone in the 1920s.

“Machine Gun” Jack McGurn was the most feared of Capone’s killers, and he spent every night at The Green Mill, openly sipping liquor in one of the green-plush upholstered booths.

In 1927, he took his love of the Green Mill to new heights (or depths). He was outraged that the club’s star attraction, singer and comedian Joe E. Lewis, refused to renew his contract. Lewis went to a competitor instead, playing to a full house at the New Rendezvous the next night. Each day that he packed the house there, McGurn got angrier.

A few days later he confronted Lewis (photo) at his hotel, the New Commonwealth. McGurn had two friends with him and all three of them had their hands shoved in their pockets. He told Lewis that they missed him at the club and that “the old Mill’s a morgue without you.”

Lewis refused to come back to the Green Mill.

On November 27, three of McGurn’s men stormed into Lewis’ hotel suite, beat him and then cut his throat from ear to ear. The comedian survived the attack, and was even able to recover his singing voice, but McGurn's boss--Al Capone, was very unhappy with his lieutenant's behavior. He advanced Lewis $10,000 so that the performer could get back on his feet.

While this story was the biggest news to hit the north side of Chicago, another north side story didn't receive the same kind of attention. For Cubs fans, it turned out to be the biggest story of the decade.

While newspaper headlines blared the story of the McGurn/Lewis confrontation, the Cubs made a trade. They traded their second baseman Sparky Adams and outfielder Pete Scott for a disgruntled star outfielder on the Pittsburgh Pirates. His name was Kiki Cuyler.

Cuyler went on to lead the Cubs to pennant in 1929, a near miss in 1930, and another pennant in 1932. Even though the Cubs didn't win the World Series in either year, Cuyler wasn't the reason. He hit .300 in the 1929 Series and led the team in RBI. In 1932, he homered in the same game that Babe Ruth supposedly called his shot.

Cuyler also provided something for the Cubs that they wouldn't have for another 45 years: speed. He led the league in stolen bases in 1929 and 1930. Between 1930 when he stole 37 bases and 1975 when Jose Cardenal stole 34, not a single Cubs player stole more than 30 bases in a season.

Machine Gun Jack McGurn's impact would be felt in an entirely different way. After allegedly being the mastermind of the St. Valentines Day massacre, McGurn was gunned down on the anniversary of that crime a few years later. The killers left this poem on his body...




You’ve lost your job.
You’ve lost your dough,
Your jewels and handsome houses.
But things could be worse, you know.
You haven’t lost your trousers.

McGurn died in 1936. Cuyler passed away in 1950.

But the Green Mill still stands today.