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With Valentine’s Day on the Horizon, let’s Exhume ex-Boxer ‘Machine Gun’ McGurn

With Valentine’s Day on the Horizon, let’s Exhume ex-Boxer ‘Machine Gun’ McGurn
Feb. 14, which this year falls on a Friday, is Valentine’s Day, more formally St. Valentine’s Day. It’s a day identified with romance, but for students of organized crime, it summons up an image of a different sort. On Valentine’s Day in 1929, at a warehouse in the Lincoln Park district of Chicago, seven men were lined up against a wall and murdered in cold blood by four intruders with machine guns and shotguns. The infamous St. Valentine’s Day Massacre was the most sensational news story during the Prohibition Era when many of America’s cities, most notably Chicago, were roiled by deadly turf wars between rival bootlegging factions.
It shouldn’t surprise us that a former boxer was one of the alleged perpetrators. During the Prohibition years, bootleggers were well-represented among the ranks of boxing promoters and managers. Philadelphia’s Max “Boo Boo” Hoff reportedly had the largest boxing stable in the country. In New York, Owney Madden was purportedly the brains behind the consortium that controlled future heavyweight champion Primo Carnera.
That brings us to Jack McGurn, but first a little context. Prohibition was the law of the land from 1920, when the Volstead Act took effect, until 1933 when the ill-conceived law was repealed. Prohibition did not fetter America’s thirst for alcoholic beverages but arguably encouraged it. Confirmed beer drinkers didn’t stop drinking beer because it was illegal. Restaurateurs at high-end establishments didn’t stop selling cognac and brandy; they just did it more discreetly. Speakeasies became fashionable.
Big money awaited entrepreneurs willing to risk arrest by flouting the law, either by opening distilleries and breweries or importing alcohol with Canada the leading supplier.
In Chicago and environs, circa 1929, two of the kingpins of the bootlegging trade were “Scarface” Al Capone and George “Bugs” Moran. They were bitter rivals. The warehouse at which the seven men were assassinated housed some of Moran’s delivery trucks. The victims were members of his gang.
Al Capone wasn’t directly involved. On Feb. 14, he was in Florida where, among other things, he was finalizing arrangements to host a bevy of A-list sportswriters at his lavish Miami Beach estate; the scribes were coming to town to cover the heavyweight title eliminator between Jack Sharkey and Young Stribling. But the hired guns, who stormed into Moran’s warehouse at 10:30 on a snowy Valentine’s Day morning, were presumed to be working for Capone and the one henchman whose name stood out among the usual suspects was Jack McGurn. He had purportedly saved Capone’s life on two occasions by intercepting would-be assassins out to kill his boss and shooting them dead. Of all his underlings, Capone was said to be especially fond of McGurn.

Machine Gun Jack McGurn
It had long been the custom of Jewish and Italian boxers to adopt Irish-sounding ring names. McGurn was born Vincenzo Gibaldi in 1902 in the Sicilian seaside city of Licata and lived in Brooklyn before moving with his widowed mother to Chicago. He had his first documented prizefight in 1921. The bout was held on a naval training ship, the U.S.S. Commodore. Prizefighting was then illegal in the Windy City, a residue of the malodorous 1900 fight between Terry McGovern and Joe Gans, but the ship was docked outside the Chicago city limits.
McGurn would have five more documented fights, the last against Bud Christiano on a strong card in Aurora, Illinois. Their six-round bout was the semi-windup. The main go was a 10-round contest between bantamweights Bud Taylor, the Terre Haute Terror, and Memphis Pal Moore, both of whom are enshrined in the International Boxing Hall of Fame.
By law, these were no-decision fights with wagers resting on the opinion of one or more ringside reporters. McGurn really had no business in the same ring with Christiano, an 84-fight veteran who had won two of three from future world lightweight title-holder Jimmy Goodrich. He took the worst of it, but was still standing at the final bell. And that was that. After only six pro fights, he hung up his gloves to pursue other endeavors and, in time, when his name appeared in the newspapers, it invariably appeared as Machine Gun Jack McGurn, the reference to the newfangled Thompson Machine Gun, colloquially the Tommy Gun, a tool with which McGurn was said to be very proficient.
The police found McGurn holed up in a Chicago hotel where he was staying with his girlfriend, Louise Rolfe, a 22-year-old “professional model and cabaret entertainer” with a 5-year-old daughter from a previous relationship that was being raised by her mother.
Louise testified that on the day of the massacre, they were in bed until noon. She said that she and McGurn had seldom left the room during their 13-day stay, having their food brought up from the hotel’s kitchen.
Louise held tight to her story and the police never did have sufficient evidence to charge the ex-boxer in connection with the crime. However, whenever the authorities were frustrated in sending a perp to prison, they had other weapons at their disposal to get their pound of flesh.
In the case of Scarface Al Capone, it was the 1913 law that authorized a federal income tax. The feds had enough circumstantial evidence to show that Al hadn’t been paying his fair share of taxes and succeeded in removing him from society. (After serving almost eight years in federal prisons, mostly Alcatraz, Capone returned to civilian life a sick man and passed away in Florida at age 48.)
In the case of Machine Gun Jack McGurn and his paramour, later his wife, the wedge was the Mann Act of 1910.
The Mann Act, most famously used to waylay heavyweight champion Jack Johnson, was aimed at brothel-keepers and immigrant flesh peddlers but was worded in such a way that it could be deployed when there was no commerce involved. It prohibited the interstate transportation of “any woman or girl for the purpose of prostitution or debauchery, or for any other immoral purpose.” (The law remains on the books but has been watered-down to decriminalize sexual activity between consenting adults.)
The feds spent thousands of hours digging up evidence to show that the couple had violated the Mann Act. They eventually got hotel receipts showing that they had registered as Mr. and Mrs. under assumed names at hotels in Florida and Mississippi during a motor trip down south. Jack was sentenced to two years in Leavenworth and Louise to four months in the county jail, but their convictions were later overturned by the Illinois Supreme Court.
What comes around, goes around, goes the saying, and it figured that Machine Gun Jack McGurn would die a violent death. The ex-boxer met his maker at 1 a.m. on Feb. 15, 1936, at a second-floor bowling alley in Chicago where he was fatally shot by two gunmen who opened fire as his back was turned. There were at least 20 people present said the story in the Chicago Tribune, but “the wall of silence, traditional among the gangsters and the people who know them, was erected high and tight.”
Was McGurn’s murder retaliation for the St. Valentine’s Day Massacre? The answer appears to be a resounding “yes.” Had the deed happened before the stroke of midnight, it would have happened on a St. Valentine’s Day, the seventh anniversary of the infamous event.
The police found a crumpled comic Valentine’s card next to McGurn’s body. On the front of the card were the figures of a man and a woman in their underwear. The verse inside read:
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.
Was this card intentionally left there by the assassins? We don’t know, but the view from here (pardon the wisecrack) is that if one were to receive a card on Valentine’s Day bearing this poem, perhaps it would be best not to leave the house.
Postscript #1: Jack McGurn’s wife, the former Louise Rolfe, routinely referenced in the press as his blonde alibi, continued to have her name pop up in the news after he died. In February of 1940, police found a gun used in a burglary in a drawer in her apartment. In 1943, she was arrested on a charge of disorderly conduct after police found her in the company of a 25-year-old Army deserter.
Postscript #2:
Al Capone refused to pose for photographs, but made an exception for his friend Jack Sharkey, the future heavyweight champion. Sharkey is pictured on the right next to Capone in this 1929 photo.
****
The Mob Museum, officially the National Museum of Organized Crime and Law Enforcement, opened 13 years ago on Feb. 14, 2012 in an old three-story building in downtown Las Vegas that was originally a federal courthouse. So, each Valentine’s Day is a special occasion at the Mob Museum, an anniversary celebrated with special events, free admission for Nevada residents, and steep discounts for tourists. (On other days of the year, a single admission during peak hours is $34.95, but there are always discounts available on-line.)
A permanent display is a reconstructed portion of the wall where the seven victims were murdered. The garage where the killings happened was demolished in 1967, but before it was torn down a collector rescued many of the bricks, some with blood-stained bullet holes, which the Mob Museum acquired. Other artifacts on display this Friday will be the two Tommy Guns used in the assault, a one-day loan from the Berrian County Sheriff’s Department in Michigan which recovered the weapons from the home of a bank robber.
For the record, there is also a mob museum, called the Gangster Museum of America, in Hot Springs, Arkansas.
A recognized authority on the history of prizefighting and the history of American sports gambling, TSS editor-in-chief Arne K. Lang is the author of five books including “Prizefighting: An American History,” released by McFarland in 2008 and re-released in a paperback edition in 2020.
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Bombs Away in Las Vegas where Inoue and Espinoza Scored Smashing Triumphs

Japan’s Naoya “Monster” Inoue banged it out with Mexico’s Ramon Cardenas, survived an early knockdown and pounded out a stoppage win to retain the undisputed super bantamweight world championship on Sunday.
Japan and Mexico delivered for boxing fans again after American stars failed in back-to-back days.
“By watching tonight’s fight, everyone is well aware that I like to brawl,” Inoue said.
Inoue (30-0, 27 KOs), and Cardenas (26-2, 14 KOs) and his wicked left hook, showed the world and 8,474 fans at T-Mobile Arena in Las Vegas that prizefighting is about punching, not running.
After massive exposure for three days of fights that began in New York City, then moved to Riyadh, Saudi Arabia and then to Nevada, it was the casino capital of the world that delivered what most boxing fans appreciate- pure unadulterated action fights.
Monster Inoue immediately went to work as soon as the opening bell rang with a consistent attack on Cardenas, who very few people knew anything about.
One thing promised by Cardenas’ trainer Joel Diaz was that his fighter “can crack.”
Cardenas proved his trainer’s words truthful when he caught Inoue after a short violent exchange with a short left hook and down went the Japanese champion on his back. The crowd was shocked to its toes.
“I was very surprised,” said Inoue about getting dropped. ““In the first round, I felt I had good distance. It got loose in the second round. From then on, I made sure to not take that punch again.”
Inoue had no trouble getting up, but he did have trouble avoiding some of Cardenas massive blows delivered with evil intentions. Though Inoue did not go down again, a look of total astonishment blanketed his face.
A real fight was happening.
Cardenas, who resembles actor Andy Garcia, was never overly aggressive but kept that left hook of his cocked and ready to launch whenever he saw the moment. There were many moments against the hyper-aggressive Inoue.
Both fighters pack power and both looked to find the right moment. But after Inoue was knocked down by the left hook counter, he discovered a way to eliminate that weapon from Cardenas. Still, the Texas-based fighter had a strong right too.
In the sixth round Inoue opened up with one of his lightning combinations responsible for 10 consecutive knockout wins. Cardenas backed against the ropes and Inoue blasted away with blow after blow. Then suddenly, Cardenas turned Inoue around and had him on the ropes as the Mexican fighter unloaded nasty combinations to the body and head. Fans roared their approval.
“I dreamed about fighting in front of thousands of people in Las Vegas,” said Cardenas. “So, I came to give everything.”
Inoue looked a little surprised and had a slight Mona Lisa grin across his face. In the seventh round, the Japanese four-division world champion seemed ready to attack again full force and launched into the round guns blazing. Cardenas tried to catch Inoue again with counter left hooks but Inoue’s combos rained like deadly hail. Four consecutive rights by Inoue blasted Cardenas almost through the ropes. The referee Tom Taylor ruled it a knockdown. Cardenas beat the count and survived the round.
In the eighth round Inoue looked eager to attack and at the bell launched across the ring and unloaded more blows on Cardenas. A barrage of 14 unanswered blows forced the referee to stop the fight at 45 seconds of round eight for a technical knockout win.
“I knew he was tough,” said Inoue. “Boxing is not that easy.”
Espinoza Wins
WBO featherweight titlist Rafael Espinosa (27-0, 23 KOs) uppercut his way to a knockout win over Edward Vazquez (17-3, 4 KOs) in the seventh round.
“I wanted to fight a game fighter to show what I am capable,” said Espinoza.
Espinosa used the leverage of his six-foot, one-inch height to slice uppercuts under the guard of Vazquez. And when the tall Mexican from Guadalajara targeted the body, it was then that the Texas fighter began to wilt. But he never surrendered.
Though he connected against Espinoza in every round, he was not able to slow down the taller fighter and that allowed the Mexican fighter to unleash a 10-punch barrage including four consecutive uppercuts. The referee stopped the fight at 1:47 of the seventh round.
It was Espinoza’s third title defense.
Photo credit: Mikey Williams / Top Rank
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Undercard Results and Recaps from the Inoue-Cardenas Show in Las Vegas

The curtain was drawn on a busy boxing weekend tonight at the T-Mobile Arena in Las Vegas where the featured attraction was Japanese superstar Naoya Inoue appearing in his twenty-fifth world title fight.
The top two fights (Inoue vs. Roman Cardenas for the unified 122-pound crown and Rafael Espinoza vs. Edward Vazquez for the WBO world featherweight diadem) aired on the main ESPN platform with the preliminaries streaming on ESPN+.
The finale of the preliminaries was a 10-rounder between welterweights Rohan Polanco and Fabian Maidana. A 2020/21 Olympian for the Dominican Republic, Polanco was a solid favorite and showed why by pitching a shutout, punctuating his triumph by knocking Maidana to his knees late in the final round with a hard punch to the pit of the stomach.
Polanco improved to 16-0 (10). Argentina’s Maidana, the younger brother of former world title-holder Marcos Maidana, fell to 24-4 while maintaining his distinction of never being stopped.
Emiliano Vargas, a rising force in the 140-pound division with the potential to become a crossover star, advanced to 14-0 (12 KOs) with a second-round stoppage Juan Leon. Vargas, who turned 21 last month, is the son of former U.S. Olympian Fernando Vargas who had big money fights with the likes of Felix Trinidad and Oscar De La Hoya. Emiliano knocked Leon down hard twice in round two – both the result of right-left combinations — before Robert Hoyle waived it off.
A 28-year-old Spaniard, Leon was 11-2-1 heading in.
In his U.S. debut, 29-year-old Japanese southpaw Mikito Nakano (13-0, 12 KOs) turned in an Inoue-like performance with a fourth-round stoppage of Puerto Rico’s Pedro Medina. Nakano, a featherweight, had Medina on the canvas five times before referee Harvey Dock waived it off at the 1:58 mark of round four. The shell-shocked Medina (16-2) came into the contest riding a 15-fight winning streak.
Lynwood, California junior middleweight Art Barrera Jr, a 19-year-old protégé of Robert Garcia, scored a sixth-round stoppage of Chicago’s Juan Carlos Guerra. There were no knockdowns, but the bout had turned sharply in Barrera’s favor when referee Thomas Taylor intervened. The official time was 1:15 of round six.
Barrera improved to 9-0 (7 KOs). The spunky but outclassed Guerra, who upset Nico Ali Walsh in his previous outing, declined to 6-2-1.
In the lid-lifter, a 10-round featherweight affair, Muskegon Michigan’s Ra’eese Aleem improved to 22-1 (12) with a unanimous decision over LA’s hard-trying Rudy Garcia (13-2-1). The judges had it 99-01, 98-92, and 97-93.
Aleem, 34, was making his second start since June of 2023 when he lost a split decision in Australia to Sam Goodman with a date with Naoya Inoue hanging in the balance.
Check back shortly for David Avila’s recaps of the two world title fights.
Photo credit: Mikey Williams / Top Rank
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Canelo Alvarez Upends Dancing Machine William Scull in Saudi Arabia

Saul “Canelo” Alvarez, who has acquired a new nickname – “The Face of Boxing” – is accustomed to fighting on Cinco De Mayo weekend, but this year was different. For the first time, Canelo was fighting outside the continent of North America and entering the ring at an awkward hour. His match with William Scull started at 6:30 on a Sunday morning in Riyadh.
In the opposite corner was 32-year-old William Scull, an undefeated (23-0) Cuban by way of Germany, whose performance was better suited to “Dancing With the Stars” than to a world title fight. Constantly bouncing from side to side but rarely letting his hands go, Scull frustrated Canelo who found it near-impossible to corner him, but one can’t win a fight solely on defense and the Mexican superstar was returned the rightful winner in a bout that was a fitting cap to a desultory two days of Saudi-promoted prizefighting. The scores were 115-113, 116-112, and 119-109. In winning, Canelo became a fully unified super middleweight champion twice over.
Terence Crawford was in attendance and HE Turki Alalshikh made it official: Crawford (41-0, 31 KOs) and Canelo (63-2-2, 39 KOs) will meet in the Fight of the Century (Alalshikh’s words) on Sept. 12 in Las Vegas at the home of the city’s NFL team, the Raiders. For whatever it’s worth, each of Canelo’s last seven fights has gone the full 12 rounds.
Semi-wind-up
In a match between the WBC world cruiserweight title-holder and the WBC world cruiserweight “champion in recess” (don’t ask), the former, Badou Jack, brought some clarity to the diadem by winning a narrow decision over Noel Mikaelian. One of the judges had it a draw (114-114), but the others gave the fight to “Jack the Ripper” by 115-113 scores.
A devout Muslim who is now a full-time resident of Saudi Arabia, the Sweden-born Jack, a three-division title-holder, had the crowd in his corner. Now 41 years old, he advanced his record to 29-3-3 (17). It was the first pro loss for Mikaelian (27-1), a Florida-based Armenian who was subbing for Ryan Rozicki.
The distracted CompuBox operator credited Mikaelian with throwing 300 more punches but there was no controversy.
Tijuana’s Jaime Munguia, a former junior middleweight title-holder, avenged his shocking loss to Bruno Sarace with a unanimous 12-round decision in their rematch. This was Munguia’s first fight with Eddy Reynoso in his corner. The scores were 117-111 and 116-112 twice.
Surace’s one-punch knockout of Munguia in mid-December in Tijuana was the runaway pick for the 2024 Upset of the Year. Heading in, Munguia was 44-1 with his lone defeat coming at the hands of Canelo Alvarez. Munguia had won every round against Surace before the roof fell in on him.
Surace won a few rounds tonight, but Munguia was the busier fighter and landed the cleaner shots. It was the first pro loss for Surace (26-1-2) and ended his 23-fight winning streak. The Frenchman hails for Marseilles.
Heavyweights
In a 10-round heavyweight match fought at a glacial pace, Martin Bakole (21-2-1) and Efe Ajagba (20-1-1) fought to a draw. One of the judges favored Ajagba 96-94 but he was outvoted by his cohorts who each had it 95-95.
Bakole, a 7/2 favorite, came in at 299 pounds, 15 more than he carried in his signature win over Jared Anderson, and looked sluggish. He was never able to effectively close off the ring against the elusive Ajagba who fought off his back foot and failed to build on his early lead.
The fight between the Scotch-Congolese campaigner Bakole and his Nigerian-American foe was informally contested for the heavyweight championship of Africa. That “title” remains vacant.
In a 6-rounder, heavy-handed Cuban light heavyweight Brayon Leon, a stablemate of Canelo Alvarez, was extended the distance for the first time while advancing his record to 7-0 at the expense of Mexico’s Aaron Roche (11-4-1). Leon knocked Roche to the canvas in the fourth round with a right-left combination, but the Mexican stayed the course while eating a lot of hard punches.
Photo credit: Leigh Dawney / Queensberry Promotions
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