He Was Capone’s Fixer — Capone Had Him Shot When He Asked His Cut – HT

 

 

 

February 15th, 1936, approximately 1:00 in the morning. The Avenue Recreation Bowling Alley sits at 805 North Milwaukee Avenue, a two-story brick building on Chicago’s Near Northwest Side, where the lanes stay open past midnight and the crowd thins to regulars and insomniacs. On the second floor, a man in a gray suit, matching vest, spats, and polished black shoes is bowling with two companions.

 His name, depending on who you ask, is Vincent Gibaldi, or Vincent D’Oro, or Jack McGurn. He’s 33 years old. He’s been drinking. On the wooden bench behind his lane, sits a Valentine’s Day card. Someone left it for him earlier that evening, handed it to the front desk, addressed to McGurn by a name most people in this bowling alley don’t recognize.

The card is a cheap novelty print. It shows a cartoon couple in shabby clothes selling off their possessions. Inside, a four-line verse. “You’ve lost your job, you’ve lost your dough, your jewels and cars and handsome houses, but things could still be worse, you know. At least you haven’t lost your trousers.

” McGurn doesn’t leave. He keeps bowling. Three men in heavy overcoats come up the stairs. They don’t speak. The first shotgun blast catches McGurn before he turns fully around. Two more rounds, handguns, close range, strike him in the head and back. He drops between the lanes, face down on the hardwood, arms loose at his sides.

 The men descend the stairs and walk out into the February cold. Approximately 20 people are in the building. Not one of them will remember seeing a thing. When police arrive, they find the Valentine’s card still sitting on the bench. Inside, they find McGurn’s body in the suit he always wore, tailored, pressed, shoes freshly shined, as though he’d been expecting to be seen.

They don’t find a weapon on him. The man who’d carried a gun every day for a decade walked into a bowling alley on the anniversary of the most famous massacre in American criminal history, with nothing in his pockets but lint and a few crumpled bills. Seven years and one day earlier, Jack McGurn had orchestrated the execution of seven men in a North Clark Street garage, the crime that made Al Capone untouchable and made McGurn the most feared man in Chicago.

The newspapers called it the Saint Valentine’s Day Massacre. They never proved McGurn planned it. They never had to. Everyone knew. And everyone knew something else by 1936. Something the newspapers didn’t bother reporting because it didn’t fit the legend. The man who’d built Capone’s enforcement arm through violence, who’d been treated like an honorary brother in the Capone family, who’d lived in a 3,200 square-foot bungalow in Oak Park under a false name with a woman the tabloids called the Blonde Alibi, that man had

spent his final years covering 50-cent bets at suburban horse tracks, stripped of every racket he’d ever held, begging the organization he’d helped create to let him back in. They told him no. He pushed. He threatened. He demanded his cut of the machine he’d spent a decade feeding with other men’s blood. They answered him in a bowling alley on Valentine’s Day with a card that told him he had nothing left.

 And that’s the story most people don’t know. The one that starts after the famous name and the famous crime. Not Machine Gun Jack McGurn, the legend, the man underneath it. Who he was before Capone found him, what he did to earn the name, what it cost him to carry it, and why the organization that owed him everything decided he was worth less than the price of a novelty greeting card.

 His birth name was Vincenzo Antonino Gibaldi, and he entered the world on July 2nd, 1902 in Licata, a fishing town on the southern coast of Sicily. His Italian birth certificate confirms the date, though American records would later contradict it. McGurn himself gave different ages depending on the circumstance. He crossed the Atlantic with his mother on the SS Vincenzo Florio, arriving at Ellis Island on November 24th, 1906.

Four years old, carrying nothing documented beyond a surname that would be abandoned twice before he turned 25. The family settled first in Red Hook, Brooklyn. His mother eventually remarried a Chicago grocer named Angelo DeMora, and the boy became Vincenzo DeMora, moved to the Taylor Street neighborhood of Little Italy on Chicago’s West Side, and grew up stocking shelves and making deliveries in his stepfather’s small shop.

Angelo DeMora was not a criminal. He was a quiet man who ran a legitimate business in a neighborhood where legitimate businesses paid for the privilege of existing. The Genna brothers, six Sicilian siblings who controlled a massive moonshine operation in Little Italy, ran a protection racket that squeezed every merchant on Taylor Street.

On January 28th, 1923, when Angelo DeMora was shot and killed outside his grocery. He’d either refused to pay or couldn’t meet the price. Accounts vary. What doesn’t vary is what the Genna enforcers reportedly said about him afterward. They called him a nickel-and-dimer, a man too small to bother collecting from properly, barely worth the bullet.

Vincenzo was 20 years old. The murder did something to him that wouldn’t fully surface for 3 years, but never left. A cold, patient fury that reorganized his personality around a single objective. He took up boxing first, fighting as Battling Jack McGurn, because Irish names drew better bookings and bigger crowds on the Chicago circuit.

 He was short, but very strong, a welterweight with fast hands and a jaw that couldn’t absorb punishment. The boxing career didn’t last. The name did. By February of 1926, McGurn had tracked down and killed three of the men connected to his stepfather’s murder, all within 8 days. His signature, according to multiple accounts, was a nickel pressed into the dead man’s palm.

The insult returned. The debt collected at the exchange rate the killers themselves had set. That efficiency, the planning, the patience, the ability to locate targets and execute without hesitation, caught the attention of the one man in Chicago who valued those qualities above all others. Al Capone didn’t recruit impulsive killers.

 He recruited men who could solve problems that required both violence and discipline. McGurn had both, and he had something else, a motive that would never expire. He wasn’t killing for money. He was killing because the world had taught him that the only people who survived were the ones willing to do what he’d just done.

Capone recognized that and offered him a place in the organization. What followed was a decade that turned a grieving stepson into the most dangerous man in Prohibition era Chicago. McGurn rose to become Capone’s chief bodyguard and primary hitman, a position that carried both extraordinary trust and extraordinary proximity to power.

Multiple accounts from the period describe Capone treating McGurn like a member of his own family, an honorary brother afforded privileges that career soldiers twice his age never received. The reason was simple. McGurn delivered results that no one else in the organization could match, and he did it with a precision that made the violence feel almost administrative.

The documented body count attributed to McGurn ranges from 22 to 30 kills, though the true number is likely higher. On October 11th, 1926, he participated in the assassination of North Side gang leader [ __ ] Weiss, shot from a second-floor window across from Holy Name Cathedral on North State Street. He eliminated at least four out-of-town hitmen who’d come to Chicago to collect Joe Aiello’s bounty on Capone, a contract variously reported at $25,000 to $50,000.

In November of 1927, he walked into a restaurant and slashed the throat of comedian Joe E. Lewis, severing his vocal cords and cutting part of his tongue, because Lewis had left McGurn’s nightclub, the Green Mill on North Broadway, to perform at a rival venue. Lewis survived. Capone, the who disapproved of the attack’s publicity, gave Lewis $10,000.

McGurn kept 

the Green club became the center of McGurn’s personal empire.

He held a 25% ownership stake and turned it into one the operation that broke every rival gang in Chicago, had taken bullets and beatings and a public enemies listing that destroyed any chance of a normal life. The organization used every year of it. And when the era changed and his kind of work fell out of fashion, they took back everything he’d earned and told him to disappear.

Does a man who built something with his hands, even if what he built was built through violence, have a right to what it became? Or does the machine always belong to whoever holds the keys today, regardless of who forged them? Tell me what you think in the comments. The killing was precise and unhurried, which was itself a message.

 The suspected shooters, Claude Maddox and Jack White, acting on Nitti’s direct orders, walked into a public bowling alley, climbed a flight of stairs in full view of 20 witnesses, executed McGurn with a shotgun and two handguns, descended the stairs, and left. No masks, no rush. 20 people in the building developed what the Chicago press called Chicago amnesia, a collective failure of memory so complete that police couldn’t produce a single witness statement describing the killers’ faces, their clothing, or their direction of departure.

The Valentine’s card was never traced to its sender. Its timing, delivered on the evening of February 14th, the seventh anniversary of the massacre, was either a coincidence or a flourish so deliberate it bordered on theatrical. The verse about losing everything was accurate. McGurn had lost the Green Mill, the nightclubs, the golf course, the bungalow, the money, and finally the only thing that had kept him alive, the belief that the organization still needed him.

 Three weeks later, on March 2nd, the 1936, McGurn’s half-brother Anthony DeMory walked into a Chicago pool hall and was shot dead by three masked men. DeMory had made a public declaration after McGurn’s funeral. He told reporters he knew who killed his brother and he intended to get them. The Outfit answered that declaration the same way it had answered McGurn’s demand, quickly, in a public place, with witnesses who remembered nothing.

The DeMora family had now lost two men to the same lesson, that asking for what you believe you’re owed in a world where debts are settled with bullets is the last thing you ever do. The Capone family sent a 6-ft tall flower arrangement to McGurn’s funeral. The card read simply, “From Al.” It was a gesture of loyalty from relatives who didn’t know, couldn’t have known, that Alphonse Capone, while locked in Alcatraz and deteriorating from late-stage syphilis that was slowly destroying his brain, had never been told McGurn was dead.

The flowers came from a family honoring a bond that the man at its center could no longer remember. Capone would be released in 1939, mentally reduced to the capacity of a 12-year-old child, and would die in his Florida estate in 1947 without ever learning what happened to the man he’d once called brother. No one was ever charged with McGurn’s murder.

 No one was ever charged with Anthony DeMory’s murder. The bowling alley at 805 North Milwaukee Avenue still stands. The building is there, though the lanes are long gone, replaced by whatever the neighborhood needed more than a place to bowl at 1:00 in the morning. The Green Mill is still open. It’s still serving drinks at 4802 North Broadway.

 It’s original Art Deco interior intact. Capone’s booth still positioned to watch both entrances, a trapdoor behind the bar still leading down to tunnels that once moved whiskey and men. McGurn’s Oak Park bungalow at 1224 Kenilworth Avenue still stands as a private residence. It went on the market in 2019 for $469,000, a regular stop on gangster walking tours where guides tell visitors about the Valentine’s Day Massacre and the blonde alibi and the life that was lived behind those walls under a name that wasn’t real. McGurn himself is buried at Mount

Carmel Cemetery in Hillside, Illinois, under the name on his birth certificate, Vincenzo Gibaldi. The headstone is modest. Nothing on it announces who lies beneath. Walk a few minutes in any direction through that same cemetery and you’ll pass Al Capone’s grave and Frank Nitti’s and Dean O’Banion’s and [ __ ] Weiss’s and Sam Giancana’s.

The men who built Chicago’s underworld, who killed for each other and killed each other across two decades of American history, now share the same quiet suburban Catholic ground. Their headstones stand closer together than the lives they contained ever were.