The St. Valentine’s Day Massacre Follow-Up Murder: Capone’s Ace Hitter Hit Himself On Anniversary Of Historic Crime

Less than a decade after being in on the planning and execution of the infamous 1929 St. Valentine’s Day Massacre, Chicago mob hitman Vincent (Machine Gun Jack) McGurn was slain in a bowling alley almost seven years to the day he and several mob associates gunned down eight members of a competing Windy City bootlegging gang on orders of the legendary Midwest mafia boss Al (Scarface) Capone. McGurn was shot dead after a Valentine’s Day date in the early hours of February 15, 1936 at Avenue Recreation Bowling Alley on Milwaukee Avenue, 80 years ago this week. The three gun-wielding assassins left a Valentine’s Day greeting card near McGurn’s bullet-riddled body (at the bowling alley’s front desk to be exact).

The card read, “You’ve lost your job, you’ve lost your dough. Your jewels, your car, your handsome houses. But things could still be worse, you know. You could have lost your trousers.” 

McGurn was 33 years old and semiretired from his Chicago Outfit activities following Capone’s incarceration four years earlier. He sported a well-earned reputation for ferocity and athleticism.

At the time of his slaying, McGurn, a favorite Capone strong arm and former bodyguard of his in the mid-to-late 1920s, was working as a country-club golf pro at Evergreen Golf Course on Western Avenue. He actually played in a PGA Tour event, the 1933 Western Open, in Olympia Fields, Illinois, carding outings of 83 and 86 and falling short of making the cut by 14 strokes.

McGurn’s murder is attributed to either the lingering bad blood between McGurn and remnants of Capone’s Northside Irish rivals, the victims of the St. Valentine’s Day Massacre or Capone’s cousin and successors, Frank (The Enforcer) Nitti, who McGurn was said to be on uneasy terms with since Capone was locked up on tax evasion charges in the spring of 1932. Nobody was ever charged and put on trial for McGurn’s assassination.

Born Vincent Gibaldi in Sicily, the rechristened Machine Gun Jack McGurn joined the Capone Southside Italian mob, eventually known simply as “The Outfit,” as a young man in the early 1920s, after finishing a pro boxing career fighting under the name Battling Jack McGurn (aspiring Italian prize fighters in the first part of the 20th Century frequently changed their last name to sound Irish in order to get better bookings in the ring). He quickly gained Capone’s attention and became one of Scarface’s most-trusted lieutenants. Boyishly handsome and always dapperly dressed and coiffed belied a viciousness and raw ambition as a hoodlum – his avenging the gangland murder of his stepfather by brutally wiping out the entire three-man hit crew responsible in 1923 cemented his reputation as a fierce, up-and-comer in the volatile Prohibition Era Chitown underworld.

Besides watching Capone’s back and shuttling him around town at the height of his power and fame, McGurn earned his mob nickname as a “shooter” for Capone thug Claude (Screwy) Maddox and his Circus Gang, a well-oiled wing of Capone’s empire of vice, booze and corruption. Maddox is credited with being the first Chicago ‘Machine Gun king,’ as his faction of the Outfit was known for their mastery in the use of the then-brand new gangland toy.

McGurn owned a piece of the Green Mill, the famous Northside Chicago bling pig, lounge and jazz club and once notoriously cut the tongue of the mouth of a headlining comedian and singer at the club named Joe E. Lewis threatening to leave for employment at another establishment. The bloody incident was depicted in the 1957 film The Joker’s Wild with Frank Sinatra portraying a character based on Lewis.

Scarface Capone’s war with his enemies on the Northside in Chicago’s Irish mob reached a crescendo in 1929. The Northsiders were led at that time by George (Bugs) Moran and Capone ordered the slaughter of Moran and his men at a garage on Clark Street they would usually convene at each morning. While Moran avoided getting killed by being late, seven of his soldiers (including Moran’s preeminent pair of enforcers and executioners the Gussenberg brothers, Frank & Peter) and a gang mechanic were lined up against a wall and gunned down by a hit team dressed in police uniforms.

It’s believed McGurn was tapped by Capone to oversee the coordination and carrying out of what was dubbed by the press The St. Valentine’s Day Massacre, an eye-grabbing headline-anchor splashed across the front of newspapers spanning the globe, however never faced any charges in the world-famous crime. His defense to the accusations became known as “The Blonde Alibi.” He claimed to have spent the entire morning in bed with Louise Rolfe, his knockout golden-haired beauty of a wife and one of the Windy City’s original gun molls. Just prior to heading to the bowling alley that fateful day in 1936, Machine Gun Jack had taken Rolfe out on a Valentine’s Day date to the Green Mill.

McGurn’s step brother Anthony was murdered in a pool hall less than a month later by three gunmen matching the description of the three assailants who opened fire with machine guns on Machine Gun Jack in the bowling alley. Two of McGurn’s bodyguards were said to be in on the job.

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  1. Erik

    Hey Scott… you are aware of the alternative theory on SVDM that fits the narrative a little neater than putting it on the Outfit? I think this piece of OC history needs to be corrected, just like we all know that OC had nothing to with JFK’s assassination.