Jack McGurn in The St. Valentine’s Day Massacre

Clint Ritchie as "Machine Gun" Jack McGurn in The St. Valentine's Day Massacre (1967)

Clint Ritchie as “Machine Gun” Jack McGurn in The St. Valentine’s Day Massacre (1967)


Clint Ritchie as “Machine Gun” Jack McGurn, born Vincenzo Gabaldi, Chicago mob enforcer

Chicago, Winter 1928

Film: The St. Valentine’s Day Massacre
Release Date: June 30, 1967
Director: Roger Corman


The St. Valentine’s Day Massacre is one of the few true incidents from mob lore to have expanded into mainstream pop culture. The killing of seven men affiliated with Chicago’s North Side Gang on February 14, 1929, startled and intrigued the public with its brutality, and the event became symbolic of the ugly violence that permeated through Prohibition-era America. The event was dramatized in Scarface (1932), before Prohibition was even repealed, and would eventually be so widely known that it was parodied in films like Some Like It Hot (1959) and even an episode of The Golden Girls.

Crime historians and investigators have pieced together solid theories about what really happened in that Chicago garage 90 years ago today when four armed men—two dressed in police uniforms—stormed in, opened fire, and promptly escaped, leaving only a dog named Highball surviving to tell the tale.

When the incident and Capone’s story as a whole was adapted for Roger Corman’s The St. Valentine’s Day Massacre, the story was presented in the docudrama format that had introduced audiences to the Chicago mob’s exploits in the ABC TV series The Untouchables, though it was actually an earlier CBS Playhouse 90 episode from 1958, “Seven Against the Wall”, that provided the basis for this movie. After Corman’s willing first choice Orson Welles was kicked off the production by Fox for being “unpredictable,” Jason Robards was cast for an intense—if not visually identical—performance as the infamous Al Capone while Clint Ritchie swaggered across the screen as his smooth bodyguard and enforcer Jack McGurn.

The real "Machine Gun" Jack McGurn and his "Blonde Alibi", Louise Rolfe, after their 1931 wedding.

The real “Machine Gun” Jack McGurn and his “Blonde Alibi”, Louise Rolfe, after their 1931 wedding.

Born Vincenzo Gabaldi on July 2, 1902, the future mastermind of the St. Valentine’s Day Massacre emigrated from Sicily with his mother when he was four years old to join his father in the United States. The teenage Vincenzo took the name “Battling” Jack McGurn during his fledgling boxing career, a career that was derailed either by the lure of a life working for Al Capone or by the call for vengeance after the murder of his stepfather, Angelo DeMora. While DeMora had been killed by Black Hand extortionists, the romanticized theory that McGurn turned to a life of crime when avenging his death doesn’t take into account the fact that McGurn was already on the Chicago Outfit’s payroll when DeMora was killed in January 1923.

Six years later, when Capone was looking to rid himself of his North Side competition once and for all, the mob boss supposedly called upon McGurn to devise a plan that would wipe out rival boss George “Bugs” Moran and his gang. The mass murder that resulted on the morning of Thursday, February 14, 1929, became infamous as the St. Valentine’s Day Massacre, as four still unconfirmed gunmen lined up seven of Moran’s associates against a wall inside the SMC Cartage Company on North Clark Street and shot them to pieces with Thompson submachine guns and shotguns. Ironically, Moran escaped this bloody fate when he saw a decoy police car—part of McGurn’s plan—and got spooked. While the victims did include bona fide gang members like the violent Gusenberg brothers, the seven killed also included mere associates like optician Reinhardt H. Schwimmer and mechanic John May.

As Capone’s trusted triggerman, suspicion naturally fell upon McGurn, who was swiftly taken into custody. However, he was famously exonerated by the testimony of Louise Rolfe, his glamorous girlfriend, who described in detail how the couple’s amorous Valentine’s Day plans prevented McGurn from being anywhere near the SMC Cartage Company, and certainly not with a deadly weapon in his hand. Rolfe, who would marry McGurn two years later, became notorious as the “Blonde Alibi” and came to embody the classic gangster’s moll.

The St. Valentine’s Day Massacre marked the beginning of the end of Capone’s rule over Chicago as the embattled boss found himself facing increasing legal pressure. In October 1931, Capone was convicted of tax evasion and sentenced to eleven years in federal prison. The remnants of his gang fell into place under former enforcer Frank Nitti, but McGurn found himself increasingly alienated from the mob and returned to his passion for sports, becoming a silent partner in the Evergreen Golf Course and competing locally under his real name. On the second day of the Western Open golf championship in August 1933, police actually obeyed McGurn’s request to allow him to finish playing his second day before taking him into custody. (For the record, Macdonald Smith won the championship.)

Less than three years later, McGurn was bowling at the Avenue Recreation bowling alley on the second floor of 805 North Milwaukee Avenue in Chicago when three men drew handguns and shot the ex-gangster four times, leaving him for dead on the floor in an eerie reenactment of a scene from Scarface, the pre-Code crime film made four years earlier with his famous boss inspiring the title character. McGurn died instantly that evening, February 15, 1936, seven years and one day after the bloody massacre he masterminded on behalf of the ruthless Al Capone.

Happy Valentine’s Day.

What’d He Wear?

The St. Valentine’s Day Massacre was released just a month before Bonnie and Clyde, a cinematic phenomenon that would give birth to a decade’s worth of low-budget Depression-era crime dramas of varying quality. Unlike some lower budget gangster movies of the late ’60s and ’70s that seemed to repurpose “period” costumes (and hairstyles) from the era they were produced rather than the intended setting, the uncredited costume team for Roger Corman’s The St. Valentine’s Day Massacre put in a fair effort to replicate the actual fashions of the waning years of the roaring ’20s… even if the lanky Jason Robards isn’t exactly a perfect visual recreation of the famously corpulent Al Capone.

As Capone’s loyal liquidator Jack “Machine Gun” McGurn, Clint Ritchie wore a number of period-detailed suits, anchored by a gray chalk-striped flannel business suit that he wears most frequently. The double-breasted jacket’s broad lapels are so wide as to threaten tickling his shoulders, sweeping across his torso like crossed cutlasses. The jacket has six buttons with two to close, though Clint Ritchie’s tall 6’1″ frame means that even the full wrap of the 6×2-button front shows a considerable amount of shirt and tie above the fully fastened front.

McGurn works the room in his Mafia-flavored business suit.

McGurn works the room in his Mafia-flavored business suit.

McGurn’s jacket has wide, padded shoulders consistent with the powerful “gangster suit” profile that emerged during the era, enhanced by a suppressed waist and ventless back that keeps the skirt straight and simple around his waist and hips, drawing all attention to the emphasized and broadened chest area. The sleeves are roped at the heads and have four buttons at the cuffs. The hip pockets are straight and jetted with no flaps to pull attention from the chest, where a white linen kerchief juts from the welted breast pocket.

McGurn wears a pale blue cotton shirt with a slim collar that fastens under the tie knot with a gold collar pin. The shirt’s double (French) cuffs are worn with a set of round silver-toned cuff links.


McGurn wears two ties with this outfit, both secured in place with a gold diamond stickpin worn just a few inches under the tie knot. His first neckwear is a red, white, and blue tie with the regimental stripe of the Royal Air Force, though the stripes follow the traditionally American “downhill” direction of right shoulder-down-to-left hip. The bold scarlet and navy stripes are divided by a narrow pale blue stripe that borders the bottom of each scarlet one.

McGurn's constricted pinned collar and narrow tie knot counter his wide lapels that flank a half-foot in each direction.

McGurn’s constricted pinned collar and narrow tie knot counter his wide lapels that flank a half-foot in each direction.

These woven silk ties are available for purchase directly from retailers including RAF Museum Shop, The Regimental Shop, and Amazon.

The same tie shows up for a quick vignette in McGurn’s office at the Green Mill, worn with the same suit but with a white shirt that has the same pinned collar and double cuffs as his pale blue shirt. This vignette also provides the only look at his shoes, a pair of black leather lace-ups.

Thin cigars and contraband whiskey are McGurn's idea of a quiet night in the office.

Thin cigars and contraband whiskey are McGurn’s idea of a quiet night in the office.

Another scene in McGurn’s office finds him counting a pile of cash in the same suit and shirt as before, though this time wearing a rich dark blue tie with white polka dots. In every scene set in his office, a gray felt fedora with a black grosgrain band rests unworn on his desk in front of him.

McGurn counts some ill-gotten dough in his office. Note that the shelf over his left shoulder conceals his personal armory of handguns, shotguns, and Thompson submachine guns.

McGurn counts some ill-gotten dough in his office. Note that the shelf over his left shoulder conceals his personal armory of handguns, shotguns, and Thompson submachine guns.

Ritchie’s portrayal of McGurn illustrates that the tradition of Italian-American gangsters wearing pinkie rings extends back to the Prohibition era, sporting a gold shiner on the little finger of his right hand. As a younger, more fashion-oriented member of the Chicago Outfit, McGurn would characteristically eschew the traditional pocket watch in favor of the increasingly fashionable wristwatch, wearing a gold timepiece secured to his left wrist on a tan leather strap.

How to Get the Look

Clint Ritchie as "Machine Gun" Jack McGurn in The St. Valentine's Day Massacre (1967)

Clint Ritchie as “Machine Gun” Jack McGurn in The St. Valentine’s Day Massacre (1967)

Clint Ritchie’s take on “Machine Gun” Jack McGurn brings the fashionable racketeer’s sense of style to the silver screen, combining business-appropriate dress with Mafioso flair that commands respect among his criminal peers as he presents his plan for the St. Valentine’s Day Massacre in the boardroom-like setting.

  • Gray widely spaced chalk-stripe flannel wool suit:
    • Double-breasted 6×2-button jacket with broad peak lapels, welted breast pocket, straight jetted hip pockets, 4-button cuffs, and ventless back
    • Pleated trousers with side pockets and turn-ups/cuffs
  • Pale blue cotton shirt with pinned point collar, front placket, and double/French cuffs
    • Gold collar pin
    • Round silver-toned cuff links
  • Royal Air Force regimental striped repp tie with bold scarlet and navy stripes separated by a narrow pale blue tie
  • Black calf leather lace-up shoes
  • Black dress socks
  • Gold pinky ring
  • Gold wristwatch on tan leather strap

Do Yourself a Favor and…

Check out the movie. You can also read more about Jack McGurn’s life, career, and death at My Al Capone Museum.

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