Jack McGurn — February 15, 1936

Jack McGurn planned the most infamous mass murder in American gangland history. Seven years later — almost to the day — three gunmen shot him dead in a bowling alley and left a Valentine’s card beside his body. The card mocked everything he had lost since Al Capone went to prison. The timing was the message.

Who Was Jack McGurn?

Jack McGurn was born Vincenzo Antonio Gibaldi in Sicily in 1902 and came to America as a child, growing up in Chicago’s Little Italy neighbourhood. He fell into crime early, developing the skills — and the nickname — that would define his career. Machine Gun Jack was not an honorary title. He used one.

By the mid-1920s McGurn had become one of Al Capone’s most trusted and effective lieutenants — handling enforcement, eliminations and the kind of difficult operations that required both planning ability and personal nerve. Capone valued him highly. McGurn was also, incongruously, an accomplished amateur golfer who competed in professional tournaments — a glimpse of the legitimate life he might have led.

His personal grievance against the North Side Gang was real. Bugs Moran’s men had shot him in an attempted hit, leaving him with a permanent shoulder injury. McGurn survived and filed it away. He would settle accounts at a time and place of his choosing.

The St Valentine’s Day Massacre — McGurn’s Masterpiece

In 1929 McGurn approached Al Capone with a plan. The North Side Gang under Bugs Moran had been a persistent and dangerous thorn in the Outfit’s side for years. McGurn proposed a decisive solution — lure Moran’s men to a meeting, dress Capone’s gunmen as police officers making a raid, and execute everyone inside. Capone provided the financial backing and operational approval.

McGurn organised the logistics. Two police uniforms were stolen. A car was obtained that resembled a police vehicle. The target location — a garage at 2122 North Clark Street — was identified. Moran’s men were lured there under the pretext of a bootlegging delivery on the morning of February 14, 1929.

Seven men were shot dead. Bugs Moran himself survived only because he arrived late, saw the police car outside and drove away. The St Valentine’s Day Massacre became the most notorious event of the Prohibition era and cemented Capone’s reputation as the most feared criminal in America.

McGurn was arrested after the massacre as one of the prime suspects. He avoided conviction through an alibi provided by his girlfriend Louise Rolfe — who told police she had been with him at the time of the shooting. She became known in the Chicago press as the Blonde Alibi. McGurn subsequently married her, making her a legally incompetent witness against him as a spouse under Illinois law at the time.

The Fall — After Capone

When Al Capone was imprisoned for tax evasion in 1931, the architecture of protection that had kept McGurn safe collapsed. Capone’s patronage had been the source of McGurn’s power, his income and his safety. Without it, his position in the Outfit deteriorated rapidly. New leadership under Paul Ricca and Tony Accardo had little use for McGurn — he was a relic of the Capone era, an expensive and high-profile liability in a period when the Outfit was trying to reduce its public exposure.

McGurn’s financial situation became precarious. His lavish lifestyle — the clothes, the cars, the golf club memberships — became difficult to sustain. The Valentine’s Day card left beside his body seven years later would reference this directly, mocking the distance between what he had been and what he had become.

February 15, 1936 — The Bowling Alley

805 N. Milwaukee Avenue, Chicago — The Avenue Bowling Alley today

On the evening of February 15, 1936 — the day after Valentine’s Day, seven years and one day after the massacre McGurn had planned — he was at the Avenue Recreation bowling alley on the second floor of 805 N. Milwaukee Avenue in Chicago. Whether he was aware of the anniversary’s significance is not known. He was bowling.

Three gunmen entered the building and came up to the second floor. They moved quickly and fired machine guns at McGurn at close range. He was hit from behind — the death photos show no wounds to his face, suggesting he either did not see the men until the last moment or was shot before he could turn. Against three men with machine guns, it would not have mattered either way.

Jack McGurn — shot dead in the bowling alley, February 15, 1936

McGurn died on the floor of the bowling alley. He was 33 years old.

Jack McGurn death scene

The Valentine’s Card

Beside McGurn’s body, his killers left a novelty Valentine’s Day card. It 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.”

The card was a deliberate signature. The timing — one day after Valentine’s Day, the anniversary of the 1929 massacre — made the message unmistakable. The card itself mocked McGurn’s fall from the heights of Capone-era power to the diminished, marginalised figure of his final years. It was a final humiliation, delivered by men who had waited seven years to collect the debt.

The scene — the card was left beside the body

No one was ever charged with McGurn’s murder. The most widely accepted theory points to North Side Gang associates acting in retaliation for the 1929 massacre — with one of the gunmen believed to be James Gusenberg, brother of Frank and Pete Gusenberg, two of the men McGurn had helped kill in that garage on Valentine’s Day 1929. The symmetry — if accurate — is almost too perfect.

Frequently Asked Questions — Jack McGurn

How was Jack McGurn killed?

McGurn was shot dead on February 15, 1936, in the Avenue Recreation bowling alley at 805 N. Milwaukee Avenue, Chicago — one day after the seventh anniversary of the St Valentine’s Day Massacre. Three gunmen rushed to the second floor and fired machine guns at him at close range. He was hit from behind and died on the bowling alley floor. A mocking Valentine’s Day card was left beside his body.

Who killed Jack McGurn?

The killers were never officially identified. The most widely accepted theory points to North Side Gang associates seeking revenge for the 1929 massacre — with one gunman believed to be James Gusenberg, whose brothers Frank and Pete were among the massacre victims. The timing and the Valentine’s card strongly suggest a deliberate revenge killing.

Was Jack McGurn involved in the St Valentine’s Day Massacre?

McGurn is widely believed to have planned and organised the 1929 massacre on Capone’s behalf. He arranged the stolen police uniforms, the car and the operational details. He was arrested but avoided conviction through an alibi provided by his girlfriend Louise Rolfe — the Blonde Alibi — whom he subsequently married.

What was the Valentine’s Day card left beside McGurn’s body?

A novelty card reading: “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.” A deliberate mockery of McGurn’s fall from Capone-era power, left as a signature by his killers on the anniversary of the massacre he had planned.

Who was Jack McGurn?

Born Vincenzo Antonio Gibaldi in Sicily in 1902, McGurn was one of Capone’s most trusted lieutenants — nicknamed Machine Gun Jack for his preferred killing method. He was also a skilled golfer who competed professionally. After Capone’s imprisonment in 1931 his power rapidly declined, leaving him vulnerable to the enemies he had made during his years at the top.