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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was the law of the land from 1920, when the Volstead Act took effect, until 1933 when the ill-conceived law was repealed.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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High Drama in Japan as ‘Amazing Boy’ Kenshiro Teraji Overcomes Seigo Yuri Akui

Overshadowed by countrymen Naoya Inoue and Junto Nakatani, Kenshiro Teraji embossed his Hall of Fame credentials in Tokyo tonight with a dramatic 12th-round stoppage of Seigo Yuri Akui. At stake were two pieces of the world flyweight title. A two-time world title-holder a division below (108), Teraji (25-1, 16 KOs) was appearing in his 16th world title fight.
This Japan vs. Japan matchup will go down in Japanese boxing lore as one of the best title fights ever on Japanese soil. Through the 11 completed rounds, Akui was up 105-104 on two of the cards with the Teraji up 106-103 on the third. However, judging by his appearance, Akui was more damaged. The stoppage by Japanese referee Katsuhiko Nakamura, which came at the 1:31 mark of the final round with Akui still standing, struck some as premature but the gallant Akui was well-beaten.
A second-generation prizefighter, Kenshiro Teraji, 33, came bearing the WBC 112-pound belt which he acquired this past October with an 11th round TKO of Nicaraguan veteran Cristofer Rosales. The 29-year-old Akui (21-3-1) was making the second defense of the WBA strap he won with a wide decision over previously undefeated Artem Dalakian.
Although Teraji keeps on rolling – this was his seventh straight win which began with a third-round blast-out of Masomichi Yabuki, avenging his lone defeat – things aren’t getting any easier for the so-called “Amazing Boy.” In his last three fights, which include a hard-earned majority decision over Carlos Canizales, he answered the bell for 35 rounds.
By and large, fighters in his weight class don’t age well. While Teraji is starting to slip, he has no intention of retiring any time soon. His goal, he says is to unify the title and eventually move up a notch to pursue a world title in a third weight class. The other pieces of the 112-pound title are currently the property of Mexico’s Angel Ayala who defends his IBF diadem against Yabuki later this month and LA’s Anthony Olascuaga who was in action on tonight’s undercard.
Other Bouts of Note
Olascuaga, a stablemate of Junto Nakatani, trained by 2024 TSS Trainer of the Year Rudy Hernandez, advanced to 9-1 (6) with a hard-earned unanimous decision over Hiroto Kyoguchi. The judges had it 118-110 and 117-111 (scores condemned as too wide) with the third judge having it 6-6 in rounds but scoring it 114-113 in acknowledgement of the knockdown credited to Olascuaga in round 11, the result of a short left that produced a delayed reaction.
Olascuaga was making the second defense of his WBO belt in his fifth straight trip to Japan. In his lone defeat, he was thrust against the formidable Teraji as a late sub, acquitting himself well in defeat (L TKO 9) despite having only five pro fights under his belt and having only 10 days to prepare. Kyoguchi (19-3) had previously held titles in the sport’s two smallest weight classes.
In a big upset, Puerto Rico’s Rene Santiago, thought to be well past his prime at age 32, wrested the WBO light flyweight title from Shokichi Iwata with a unanimous decision over Shokichi Iwata who was making the first defense of the title he won with a third-round stoppage of Spain’s previously undefeated Jairo Noriega. Tokyo’s Iwata was a consensus 9/1 favorite.
Santiago, who advanced to 14-4 (9), won by scores of 118-110, 117-111, and 116-112. It was the second loss for Iwata who had knocked out 11 of his first 15 opponents.
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Keith Thurman Returns with a Bang; KOs Brock Jarvis in Sydney

The combination of age and ring rust made Keith Thurman a tricky proposition against Brock Jarvis, but the 36-year-old Floridian, a former WBA and WBC world welterweight champion, had too much firepower for the overmatched Aussie, knocking out Jarvis in the third round tonight in Sydney and setting up a massive fight with Tim Tszyu.
Thurman’s career has been repeatedly interrupted with injuries. He missed all of 2023 and 2024 and this was only his second fight back since being out-pointed by Manny Pacquiao in 2019. He was slated to fight Tszyu in March of last year in Las Vegas with two 154-pound straps on the line, but pulled out with a biceps injury and was replaced by Sebastian Fundora who saddled the snakebit Tszyu with his first defeat.
Against Brock Jarvis, Thurman started slowly. The TV commentating team, which included Tszyu and Shawn Porter, had the busier Jarvis winning the first two rounds. But the savvy Thurman was simply “processing data” and found his grove in the third frame, smashing Jarvis to the canvas with a combination climaxed by a wicked uppercut. Jarvis staggered to his feet but was a cooked goose and the referee waived it off immediately when Jarvis hit the deck again after absorbing a harsh left hook. The official time was 2:19 of round three.
It was the second bad loss for Jarvis (22-2), a noted knockout puncher who had previously been stopped in the opening round by countryman Liam Paro. He hails from the Sydney suburb of Merrickville which also spawned Hall of Famer Jeff Fenech, Jarvis’s former trainer.
Thurman advanced to 37-1 with his twenty-third win inside the distance. According to Tszyu’s promoter George Rose, the match between Thurman and Tszyu will finally come to fruition on July 6, likely at the Gold Coast Convention Center in Broadbeach. That’s predicated on the assumption that Tszyu wins his next fight without complications which comes on April 6 against Minnesota’s 19-1 Joey Spencer at Newcastle, Australia.
Other Bouts of Note
Melbourne Middleweight Michael Zerafa, who also covets a match with Tim Tszyu, improved to 33-5 (21 KOs) with a seventh-round stoppage of Germany’s obscure Besir Ay (19-2) who was on the deck twice before the referee waived it off. This was the second fight back for Zerafa after getting pulverized by Erislandy Lara who stopped him in the second round in March of last year. Ay, 35, is recognized as the middleweight champion of Germany.
In a middleweight match slated for 10, Tim Tszyu’s longtime sparring partner Cesar Mateo bombed out Sergei Vorobev in the fifth round, ending the match with a spectacular one-punch KO. The 26-year-old Mateo (18-0-1, 11 KOs) is a native of Tijuana. Vorobev (20-3-2) is a 30-year-old Sydneysider born in Russia.
Thurman vs. Jarvis, a pay-per-view event in Australia, aired in the U.S. on a tape-delay on the PBC youtube channel.
Photo credit: Grant Trouville / No Limit Boxing
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Friday Boxing Recaps: Observations on Conlan, Eubank, Bahdi, and David Jimenez

Friday Boxing Recaps: Observations on Conlan, Eubank, Bahdi, and David Jimenez
March 7 was an unusually heavy Friday for professional boxing. The show that warranted the most ink was the all-female card in London, a tour-de-force for the super-talented Lauren Price, but there were important fights on other continents.
Brighton
Michael Conlan, who sat out all of 2024 on the heels of being stopped in three of his previous five, returned to the ring in the British seaside resort city of Brighton in a shake-off-the-rust, 8-rounder against Asad Asif Khan, a 31-year-old Indian from Calcutta making his first appearance in a British ring.
Conlan, a 2016 Olympic silver medalist who famously signed with Top Rank coming out of the amateur ranks, is now 33 years old. Against Khan, he was far from impressive, but did enough to win by a 78-74 score and lock in a match with Spain’s Cristobal Lorente, the European featherweight champion.
Conlan, who improved to 19-3 (9), absorbed a lot of punishment in those three matches that he lost. With his deep amateur background, Michael has a lot of mileage on him and he would have been smart to call it quits after his embarrassingly one-sided defeat to Luis Alberto Lopez. His frayed reflexes speak to something more than ring rust. Heading in, Khan brought a 19-5-1 record but had scored only five wins inside the distance.
Conlan vs Khan was the co-feature. In the main event, Brighton welterweight Harlem Eubank, the cousin of Chris Eubank Jr, improved to 21-0 (9 KOs) with a dominant performance over Conlan’s Belfast homie Tyrone McKenna. Eubank was credited with three knockdowns, all the result of body punches, before referee John Latham had seen enough and pulled the plug at the 2:09 mark of round 10. It was the fourth loss in his last six outings for the 35-year-old McKenna (24-6-1).
Harlem Eubank wants to fight Conor Benn next and says he is willing to wait until after his cousin “wipes Benn out.” Chris Eubank Jr vs Benn is slated for April 26 at Tottenham Hotspur Stadium. The North London facility, which has a retractable roof, is the third-largest soccer stadium in England.
Toronto
Local fan favorite Lucas Bahdi and his stablemate Sara Bailey were the headliners on last night’s card at the Great Canadian Casino Resort in Toronto. The event marked the first incursion of Jake Paul’s MVP Promotions into Canada.
Bahdi, who is from Niagara Falls but trains in Toronto, burst out of obscurity in July of last year in Tampa, Florida, with a spectacular one-punch knockout of heavily-hyped Ashton “H2O” Sylva. His next fight, on the undercard of Jake Paul’s match with Mike Tyson, was less “noisy” and the same could be said of his homecoming fight with Ryan James Racaza, an undefeated (15-0) but obscure southpaw from the Philippines who was making his North American debut.
Bahdi vs Racaza was a technical fight that didn’t warm up until Bahdi produced a knockdown in round seven with a sweeping left hook, a glancing blow that appeared to land behind Racaza’s ear. The Filipino was up in a jiff, looking at the referee as if to say, “this dude just hit me with a rabbit punch.”
The judges had it 99-90, 97-92, and 96-93 for the victorious Bahdi (19-0) who was the subject of a recent profile on these pages.
Sara Bailey, a decorated amateur who competed around the world under her maiden name Sara Haghighat Joo and now holds the WBA light flyweight title, successfully defended that trinket with a lopsided decision over Cristina Navarro (6-3), a 35-year-old Spaniard who “earned” this assignment by winning a 6-round decision over an opponent with a 1-4-3 record. The judges scored the monotonous fight 99-91 across the board for Bailey who improved to 6-0 and then returned to the ring to assist her husband in Lucas Bahdi’s corner.
Also
Twenty-two-year-old super bantamweight Angel Barrientes, a Las Vegas-based Hawaii native, delivered the best performance of the night with a one-sided beatdown of Alexander Castellano whose corner mercifully stopped the contest after the seventh round as the ring doctor stood in a neutral corner chatting with the referee.
The gritty Castellano, who hails from Tonawanda, New York, brought an 11-1-2 record and hadn’t previously been stopped. A glutton for punishment, he appeared to suffer a broken orbital bone. Barrientes improved to 13-1 (8 KOs).
The show was marred by an excessive amount of fluffy gobbledygook by the TV talking heads which slowed down the action and made the promotion almost unwatchable.
Cartago, Costa Rica
Fighting in his hometown, super flyweight David Jimenez scored a lopsided 12-round decision over Nicaragua’s Keyvin Lara. The judges had it 120-108, 119-109, and 116-112.
Jimenez, now 17-1, came to the fore in July of 2022 when he upset Ricardo Sandoval in Los Angeles, winning a well-earned majority decision over a 20/1 favorite riding a 16-fight winning streak. That boosted him into a title fight with the formidable Artem Dalakian who saddled him with his lone defeat.
Jimenez’s victory over Lara was his fifth since that setback. It sets up the Costa Rican for another title fight, this time against Argentina’s Fernando Martinez who acquired the WBA 115-pound title in July with an upset of Kazuto Ioka in Japan. Lara, who unsuccessfully challenged Ioka for a belt in 2016, falls to 32-7-1.
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