“Machine Gun” Jack McGurn: The Notorious Mobster

This article is a summary of the YouTube video ‘Mobster – “Machine Gun” Jack McGurn’ by Bloodletters & Badmen

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Written by: Recapz Bot

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Vincenzo from Sicily immigrated, became boxer, joined Capone, orchestrated massacre, killed.

Key Insights

  • Vincenzo was a young boy from Sicily who immigrated to the US with his parents in 1902. They settled in Chicago.
  • His father died and his mother remarried Angelo De Mori, who treated Vincenzo as his own son.
  • Vincenzo changed his name to battling Jack McGurn and pursued a career as a boxer.
  • McGurn's stepfather was killed during Prohibition, and he vowed revenge.
  • He joined Al Capone's gang, becoming one of Capone's top gunmen and earning the nickname "Machine Gun Jack McGurn."
  • McGurn carried out hits on rival gang members and those involved in his stepfather's murder.
  • He became indispensable to Capone, and they spent a lot of time together, attending games and playing golf.
  • McGurn invested his illegal profits in local nightclubs and engaged in criminal activities like assault.
  • He was targeted by rivals but survived assassination attempts.
  • In 1929, McGurn orchestrated the St. Valentine's Day Massacre, wiping out rival gang members.
  • Police suspected his involvement but lacked evidence to convict him. His lover provided him with an alibi.
  • McGurn's reputation declined after Capone went to prison, and he faced financial difficulties.
  • McGurn's nightclubs failed, and he got involved in minor drug deals.
  • Alone, penniless, and abandoned by his wife, McGurn was killed in 1936, possibly by members of the old North Side gang seeking vengeance.
  • The killers left a humorous poem and a nickel, which had become McGurn's trademark.

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On July 2, 1902, in Licata, Sicily, the young lad was the apple of his mother’s eye and just four years old when his parents immigrated to the United States. They moved around a little at first, eventually settling in the fastest-growing city at the time, Chicago.

His father died a few years later and his mother remarried Angelo De Mori, a kind man who owned a grocery store in the heart of Chicago’s Little Italy. De Mori, described by friends and neighbors as a thoughtful gentleman with old-world values, took on his new role as stepfather with pride and treated the young Vincenzo as if he were his own son. The boy was grateful and returned the sentiment, looking up to his stepfather who provided for the family and loved his mother.

Times were tough and though young Vincenzo helped out the man he called Papa in his grocery store, he dreamed of becoming a boxer. At the age of 19, he eventually got his shot. He changed his name to battling Jack McGurn because fighters with Irish names usually got better bookings. But in 1923, the would-be boxer’s world would come crashing down.

Prohibition was in full swing and his stepfather, who supplied the Jenna brothers with sugar for the making of their rot-gut gin, made someone angry. Angelo De Mori was shot and killed in broad daylight in front of his small grocery store. His stepson, Jack McGurn, vowed revenge.

J. Robert Nash writes, “The story of Jack McGurn is the age-old tale of the good-boy-turned-gangster so dear to the hearts of Warner Bros. scriptwriters. McGurn was truly a product of the 1920s, beginning his career as a clean-cut kid from the slums battling for a slice of dignity in the ring as a promising welterweight. But after the death of his stepfather, Jack abandoned his promising career as a pugilist and joined the South Side gang headed up by Al Capone, and he quickly became one of Capone’s top gunners. His proclivity with the Thompson submachine gun in Chicago’s underworld earned him the nickname Machine Gun Jack McGurn.”

In 1925, the Jenna brothers, who had worked in tandem with Capone, began declaring their independence from their downtown sponsor. McGurn was pleased when things turned sour between Capone and the Jenna brothers. It had been rumored that some of the men on the Jenna’s payroll had taken part in the killing of his stepfather. Capone wanted the Jennas wiped out and gave Machine Gun Jack McGurn the contract, who was more than eager to accept the work.

Starting in June, McGurn went after the Jenna’s top enforcers. By July 17th, he had killed six Jenna men, those he was sure were involved in his stepfather’s murder. Again, quoting J. Robert Nash, hearing that these men had called his father a nickel and a dimer, McGurn contemptuously left a nickel in the palms of each of his victims, beginning a long-standing Chicago tradition unique in the annals of organized crime.

Due to his excitement and dedication to his work, Capone became more and more dependent on the talents of Machine Gun Jack McGurn to keep order in Chi-Town. In 1927, when Sicilian Joey Aiello attempted to take over the Windy City’s bootlegging rackets, Capone called on the trusted McGurn. Aiello had put a $50,000 bounty on Capone’s head and brought in out-of-state gunners to take Scarface down.

Within hours after the paid assassins stepped off the train, McGurn had a fix on their location. He stalked them like a lion closing in on its prey, and when the time was right, he surprised the hired guns, spraying them with a volley of machine gun fire. Work like this endeared McGurn to Capone, and for a time the two became inseparable. It seemed as if McGurn was always at his boss’s side. They attended baseball games together and played countless rounds of golf.

Gus Russo, in his voluminous work, “The Outfit,” gives us this bit of trivia. It is not widely known, but McGurn was a scratch golfer who might have turned pro if he had lived. During the Western Open in Illinois, the Chicago Police Goon Squad was dispatched to the Lynx to harass McGurn, who was in danger of winning the event. “You f***ing Dago,” the cops yelled as McGurn putted on the last four holes. Their tactics worked, and Jack McGurn went into the tank at the end of the round.

But McGurn shook it off. What did he care? He was making a lot of money as Capone’s top gunner. He took his illegal profits and began purchasing interest in local nightclubs. He bought a 25% interest in the Green Mill Cabaret on Chicago’s North Side, which employed an up-and-coming singer-comedian named Joe E. Lewis. When Lewis jumped to a competing nightclub, McGurn warned him not to sign the contract. Lewis ignored the threat and signed anyway.

McGurn sent three of his ruffians to Lewis’ hotel room, where the trio beat him senseless and took out a blade and sliced up his face and throat. Was it a botched murder or thuggery gone too far? Lewis was in bad shape, but he pulled through. Unfortunately, as a result of the beating and the damage to his vocal cords, he would never sing again.

Believing the treatment was over the top, Capone himself apologized to the young Lewis and paid all of his medical bills. But he never rebuked McGurn for his actions. He was just too valuable of an asset to Big Al. But as McGurn’s reputation grew, so did the list of those who wanted to end his career.

Two times assassins caught up with their rival, filling him with lead, like he had done to so many others. Once, when McGurn was on a payphone in the lobby of the McCormick Hotel, two gunners from the Northside Mob, Pete and Frank Gusenberg, busted in with guns drawn, but machine gun Jack McGurn survived the attempted slaughter.

By 1929, the remnants of the Northside Mob, now headed up by George Bugs Moran, were still buzzing around Capone’s face like gnats on a hot summer day making a nuisance of themselves. Fed up with their antics, Capone gave the order to McGurn to finish the rivalry once for all.

On St. Valentine’s Day, disguised as policemen, members of Capone’s gang executed a supposed raid on the Northsiders, lining the men up against a wall and then opening up with a volley of bullets. When the shooting ended, seven men lay dead.

On February 27th, police arrested McGurn on suspicion that he not only had knowledge of the killings, but that he had planned and participated in the deed. The only problem? They had no proof. And as if to make their case worse, Louise Rolfe, a popular showgirl and McGurn’s lover, whom he later married so that she couldn’t be compelled to testify against him, stated that McGurn was by her side during the hours before and after the massacre. The press even dubbed the leggy Louise as the blonde alibi.

The state moved forward with their case anyway, but finally had to drop it after four delays. McGurn was released on December 2nd, much to the chagrin of police and prosecutors who believed McGurn was one of the killers.

In April 1930, the Chairman of the Chicago Crime Commission published a nationwide list of public enemies that were corrupt in Chicago and its suburbs. Machine Gun Jack McGurn was fourth on the list. The notoriety McGurn received from the list caused the outfit to turn their backs on him. The spotlight was too great.

After Capone was sent to prison and the Roaring Twenties came to a full stop during the Depressing Thirties, Machine Gun Jack McGurn began a downhill slide. His nightclubs went belly up and the new boys in charge wanted to change the way things were done in Chicago.

Trying to make ends meet, McGurn got involved in a few narcotic deals, but nothing of any consequence. And as the money ran out, like the prodigal son in Christ’s parable, he lost his plush hotel suite, his friends, and eventually even his wife abandoned him.

Alone and penniless, sources from Chicago stated that McGurn ran into some friends on February 13, 1936, the eve of the seventh-year anniversary of the St. Valentine’s Day Massacre. They were on their way to bowl a few games at the lanes on Milwaukee Avenue and convinced McGurn to come along.

During the friendly game, men carrying machine guns came charging into the place and shot Jack McGurn to death. Many believed that the gunmen represented a cadre of the old North Side gang who had personally returned to Chicago to perform this last act of vengeance.

As his body lay twitching and blood gushed out from the numerous wounds, one of the shooters, as a sign of disrespect, placed a somewhat humorous poem in his left hand 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.” In his right hand, the killers placed McGurn’s notorious trademark, a nickel.

This article is a summary of the YouTube video ‘Mobster – “Machine Gun” Jack McGurn’ by Bloodletters & Badmen