1936: Death in a West Side Bowling Alley
The Murder of "Machine Gun" Jack McGurn

One of the most fearsome of the gunmen that Al Capone kept on his payroll was “Machine Gun” Jack McGurn, a rough and tumble young Italian man who earned his nickname not from his prowess with a tommy-gun, but for his speed in the boxing ring. McGurn killed without thought and was believed to have been one of the killers responsible for the St. Valentine’s Day Massacre. And those who later killed him probably knew it for they left behind a reminder of that bloody day when his body was discovered in a West Side bowling alley.

 

James Vincenzo Gibaldi, 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 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.

 

At the start of Prohibition, the Gennas had transformed all of 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 of his competitors shot Angelo to death in front of his store on January 8, 1923.


"Machine Gun" Jack McGurn

 

McGurn never got back into the ring. He was only 19 years old, but had a mother and siblings to take care of. He picked up a gun and started working for Al Capone, who regarded him as his most trustworthy gunman. He was given the most dangerous and grisly assignments and 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 blamed for his father' death. In just over a month's time, he wiped out all of the Gennas' top men. 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 each of 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 fearsome 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 dared to cross Capone. Days after their arrival, the four men met the wrath of Jack McGurn. All of them were found riddled with machine gun bullets --- and were found 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, the city’s hottest jazz club, 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 in 1927, he 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. Lewis 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, 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 killed during the St. Valentine's Day Massacre), caught up with McGurn in a phone booth inside 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.

In early February 1929, McGurn visited Capone at his Palm Island, Fla., home for a discussion about the North Side gang run by George Moran. Ten days later, the St. Valentine's Day Massacre took place.

 

McGurn has always been connected to the massacre, although that connection was never legally proven. A teenager named George Brichet was walking past the garage when five men entered on February 14. Bricket overheard one of the men call another “Mac”. Bricket 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. 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 that, 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 began to be seen less and less with the boss and was not seen at all during Capone's tax trial, when the job of bodyguard was given over to Phil D'Andrea.
McGurn and Louise Rolfe, McGurn's so-called "Blonde Alibi"


Last photo of "Machine Gun" Jack McGurn		 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 13, 1936, the eve of 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 Ave., when remnants from the old Moran gang finally caught up with him.
805 N. Milwaukee Avenue today, site of the former Avenue Recreation Parlor

 Five men burst into the bowling alley and while three of them pretended to rob the place, the other two machine-gunned McGurn to death on the hardwood lanes.

 

At the front desk, the killers had left a comic valentine with his name on it, which read:

 

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.

 

Legend has it that, in the palm of "Machine Gun" Jack McGurn's right hand, the killers were said to have placed a solitary nickel.
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