If I were forced to name only one location in Chicago as my favorite spot connected to the days of Al Capone, it would be legendary jazz club known as the Green Mill on North Broadway.
As the city’s oldest nightclub, it’s been offering continuous entertainment since 1907 and remains today as an authentic link to not only Al Capone but to the club’s former manager ---- and Capone henchman ---- “Machine Gun” Jack McGurn.
The Green Mill opened in 1907 as Pop Morse’s Roadhouse and from the very beginning, was a favorite hangout for show business people in Chicago. In those days, actors from the north side’s Essanay Studios made the roadhouse a second home. One of the most popular stars to frequent the place was “Bronco Billy” Anderson, the star of dozens of Western silents from Essanay. Anderson often rode his horse to Pop Morse’s and the proprietor even installed a hitching post that Anderson’s horse shared with those of other stars like Wallace Beery and William S. Hart. Back then, even screen greats like Charlie Chaplin stopped in sometimes for a drink.
Around 1910, the Chamales Brothers purchased the club from the original owners. They installed a huge, green windmill on the roof and re-named the place the Green Mill Gardens. The choice of the name “Green Mill” was inspired by the infamous Moulin Rouge in Paris (French for “Red Mill”) but green was chosen so that it would not be confused with any of the red light districts in Chicago. The new owners added outdoor dancing and live entertainment in the enlarged sunken gardens and also added a rhumba room next door. The Green Mill Gardens was more of a roadhouse that spanned an entire block than a cocktail lounge in those days.
Vintage Postcard of the Green Mill Gardens
Tom Chamales later went on to construct the Riviera Theater, around the corner from the Green Mill. He and his brother leased the Green Mill to Henry Van Horne and it soon began to attract the best --- and worst --- of the late-night denizens of Chicago.
By the time that Prohibition arrived, the Green Mill had become known as the most jumping place on the north side. Jazz fans flocked to the club to savor this new and evolving musical art form, which had been born in the south but had been re-created in Chicago after World War I. The jazz crowd ignored the laws against alcohol and hid their bootleg whiskey away in hip flasks, which they eagerly sipped at the Green Mill. The club helped to launch the careers of singers who went on to become legends like Helen Morgan, Anita O’Day, and Billie Holliday. It also offered an endless procession of swinging jazz combos and vaudevillians, who dropped in to jam or just to relax between sets at other, lesser clubs.
In the middle 1920s, Van Horne gave up his interest in the place and the Chamales Brothers leased the club to Al Capone’s south side mob. Capone himself, although straying into the enemy’s territory on the north side, often enjoyed hanging out at the club, listening to the music, and drinking with friends.
In the case of the Green Mill though, it’s not the remnants of Al Capone that attracts crime buffs to the club, it’s the legend of Jack McGurn, who managed the club for Capone in the 1920s.
James Vincenzo De Mora, or Jack McGurn as he later became known, was born in Chicago’s Little Italy in 1904. He grew up as a clean-cut kid from the slums who excelled in school and was an excellent boxer. A fight promoter managed to get him into the ranks of professional fighters and at the man’s suggestion; James adopted the ring name of “Jack McGurn”. He seemed to have a great career ahead, until his father, Angelo De Mora, a grocer with a store on Halsted Street, ran into trouble with the terrible Genna brothers and McGurn stepped over the line into the world of crime.
At the start of Prohibition, the Gennas had transformed all over Little Italy into a vast commercial area of alcohol cookers. Stills were set up in almost every home, franchised by the Gennas, making homemade rotgut whiskey that was popular in neighborhood speakeasies. Angelo De Mora sold sugar to the Gennas for their operations, a relatively safe enterprise until some competitors for the position appeared on January 8, 1923. Angelo was found shot to death in front of his store.
McGurn rushed home when he heard about his father’s death. He was only 19 but he immediately took the role of head of the household, shielding his mother and five brothers from the police. The police asked him if he was afraid for his life now that he was the man of the house.
“No,” McGurn answered ominously. “I’m big enough to take care of this case myself.”
McGurn never got back into the ring. He picked up a gun and started working for Al Capone, who regarded him as his most trustworthy gunman and the man to carry out the most dangerous and grisly assignments. Within a few years, “Machine Gun” Jack McGurn was the most feared of Capone’s killers.
McGurn relished his work, especially when six of his targets were part of the Genna mob, which he believed was responsible for his father’ death. In just over a month’s time, he wiped out the Genna's top men and he learned that one of these men had referred to his father as “a nickel and dimer.” So, after each of them had been machine-gunned to death, McGurn pressed a nickel into their palms, his sign of contempt and a trademark that would be forever linked to his murders.
McGurn continued to earn his pay --- and his reputation. Joe Aiello’s feud with Capone over west side beer territories reached its peak when Aiello offered a $50,000 reward for Capone’s murder. He imported four out-of-town killers to do the job when no one in Chicago took him up on his offer. Days after their arrival, the four men met with the wrath of Jack McGurn. All of them were found riddled with machine gun bullets --- and with nickels pressed into their palms.
When not working for Capone, McGurn frequented Chicago’s hottest jazz spots and managed to become part owner of several of them through intimidation and violence. By the time he was 23, McGurn owned pieces of at least five nightclubs and managed a number of other lucrative properties. He also managed the Green Mill for Capone and was later given 25 percent of its ownership in exchange for his loyalty. This became his usual hangout and he could often be found sipping liquor in one of the green-plush upholstered booths.
McGurn was fiercely loyal to the Green Mill and so in 1927, became enraged when the club’s star attraction, singer and comedian Joe E. Lewis, refused to renew his contract, stating that he was going to work for a rival club. He opened to a packed house at the New Rendezvous the next night. Days later, McGurn took Lewis aside as he was about to enter his hotel, the New Commonwealth. McGurn had two friends with him and all three of them had their hands shoved in their pockets.
McGurn told Lewis that they missed him at the club and that “the old Mill’s a morgue without you.”
Lewis assured him that he would find another headliner and when McGurn told him that he had made his point and needed to come back, Lewis refused. He bravely turned his back on the killer and walked away.
On November 27, three of McGurn’s men stormed into Lewis’ hotel suite, beat him and then cut his throat almost from ear to ear. The comedian survived the attack though, managed to recover his singing voice and continued with his career. Capone, unhappy with McGurn’s actions but unable to rebuke one of his best men, was said to have advanced Lewis $10,000 so that the performer could get back on his feet.
A short time later, McGurn’s own career was almost cut short. Two machine gunners for George Moran, Pete and Frank Gusenberg (both later killed during the St. Valentine’s Day Massacre), caught up with McGurn in a phone booth inside of the McCormick Inn. Several bursts from their tommy guns almost finished McGurn for good but major surgery, and a long period of secluded convalescence, saved the killer. Interestingly, this phone booth can now be found in a little inn called the Ruebel Hotel in Grafton, Illinois. How it managed to end up here is anyone’s guess.
In early February 1929, McGurn visited Capone at his Palm Island, Florida home for a discussion about the north side gang run by George Moran. Ten days later, the St. Valentine’s Day Massacre took place. This hardly seems to be a coincidence!
McGurn has always been connected to the massacre, as has Fred R. “Killer” Burke. George Brichet, a teenager, was walking past the garage when the five men entered on February 14 and overheard one of the men say to another one: “Come on, Mac.” He picked out McGurn’s photograph from police mug shots. Armed with an arrest warrant, police broke into McGurn’s suite at the Stevens Hotel on February 27. As they hauled the gangster away, they were cussed out by McGurn’s sweetheart, showgirl Louise Rolfe. The press dubbed her “the blonde alibi” and she swore that McGurn was with her at the time of the murders. McGurn was later indicted but he married Louise soon after and thanks to this, she was not required to testify against him.
McGurn’s defense attorneys insisted four times that their client be brought to trial --- so that he could prove his innocence, of course. Each time, the prosecution stated that it was not ready to proceed. Under Illinois law, the prosecution was only allowed four legal delays of this kind. After they, they had to drop the case. McGurn was set free on December 2, 1929.
McGurn’s likely role in the St. Valentine’s Day Massacre led to Capone putting him “on ice”. He was just too hot to use again as an enforcer. He began to be seen less and less with the boss and was not seen at all during Capone’s tax trial, the job of bodyguard given over to Phil D’Andrea.
Once Capone went to prison, McGurn’s prestige started to slip. He busied himself with his nightclubs, most of which went under during the Depression and Louise left him when his money ran out. Alone and flat broke; McGurn met his end on February 15, 1936 ---- the day after the anniversary of the St. Valentine’s Day Massacre.
McGurn was in the middle of his third frame at the Avenue Recreation Parlor, a bowling alley located at 805 North Milwaukee Avenue, when remnants from the old Moran gang finally caught up with him. Five men burst into the place and while three of them pretended to rob the place, the other two machine-gunned McGurn to death on the hardwood lanes.
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.
In the palm of “Machine Gun” Jack McGurn’s right hand, the killers had placed a solitary nickel.