‘Machine Gun’ Jack McGurn leads list of Top 5 most notorious Mob hitmen

Faced with more than 200 unsolved gangland murders in the Brooklyn area since the early 1930s, in 1940 the District Attorney’s Office found a veteran hitman ready to make a deal to avoid execution in the electric chair at New York’s Sing Sing prison. Abe Reles agreed to detail scores of crime syndicate shootings, stabbings and strangulations, not only in Brooklyn, but all over the country.

The articulate and straight-shooting Reles regaled Assistant District Attorney Burton B. Turkus with minute details of years-old Mob hits. One day, Turkus wanted to know how Reles, personally responsible for at least 11 murders, could kill so easily.

“Did your conscience ever bother you?” Turkus asked.
Reles asked Turkus how he felt when he tried his first case as a lawyer.
“I was rather nervous,” Turkus said.
“And how about your second case?” Reles said.
“It wasn’t so bad,” Turkus replied, “but I was still a little nervous.”
“And after that?”
“Oh,” Turkus said, “after that I was all right; I was used to it.”
“You answered your own question,” Reles said. “It’s the same with murder. I got used to it.”

Reles killed without compunction for the paid hit squad dubbed “Murder Inc.” by the press. The group of killers was hired by New York’s “Commission” of top crime family bosses throughout the 1930s. Reles and other Mob torpedoes eliminated an estimated 1,000 people during that decade.

Murder was deemed necessary for syndicate bosses to end competition and keep control of money flowing from their rackets, to avenge hits by rival gangs, or to prevent a hoodlum or civilian from cooperating with the police and courts.

The use of contracted hitmen by organized crime emerged in the late 19th century with the arrival of the waves of Italian immigrants, including elements of the Sicilian Mafia, an ethnic-based crime network that basically created the modern practice of ordered killings. By the early 20th century, the lowest of characters among young Italian, Jewish, Irish and other immigrants in New York’s Lower East Side sought quick upward mobility within urban crime gangs, and easily turned to murder at the behest of Mob bosses.

Hits directed by the American version of the Mafia – or La Cosa Nostra – reached Wild West proportions, mainly on the streets of New York and Chicago, in the 1920s and ’30s before peaking again in the ’70s and largely fading away by the ’90s.

Today, tales of hitmen are mostly found in history books, at least in America. Mob hits, of course, continue from seemingly unstoppable transnational syndicates, such as the Italian ’Ndrangheta of Calabria. The rival drug cartels of Mexico murder thousands of gangsters and innocent people a year, like Prohibition-era Chicago and New York on steroids.

Who are these hitmen, virtually all of them male, taking part in the most heinous aspects of organized crime? As people, they’re almost certainly psychopathic, unable to understand or consider the emotions of others, even tempted to resort to the classic, clichéd rationale before pulling the trigger: “It’s business, not personal.”

So, here is our list of the Top 5 most notorious hitmen in Mob history. The selections are limited, the methodology subjective, to be sure. The richness of their stories, amount of researchable detail and how they fit into a greater context of their times mattered more than simply the number of victims they chalked up.

Plenty of others, while seriously considered for inclusion, did not make the cut, but may be regarded as dishonorable mentions. For instance, the “Murder Twins” of Chicago, John Scalise and Albert Anselmi, a prolific hitmen team during Prohibition, were found murdered together in 1929. Murder Inc. staffer Harry “Pittsburgh Phil” Strauss is alleged to have rubbed out more than 100 people. Former Gambino family hit man Sammy “The Bull” Gravano admitted to nearly 20 murders. Another, given far less consideration, is the late Richard “The Iceman” Kuklinski, whose delusional boasts of having killed hundreds in the New York area for Roy DeMeo – made during a paid prison interview with HBO to score money for his family – is more likely to have killed around four people.

The Top 5 are: “Machine Gun” Jack McGurn, Abe “Kid Twist” Reles, Roy DeMeo, Joe “The Animal” Barboza and Giovanni Brusca. We will profile each man in this series of five posts.

We start with Jack McGurn.

A bloody Valentine

On Valentine’s Day in 1936, “Machine Gun” Jack McGurn overslept into the early evening beside his famous “Blonde Alibi” wife, Louise Rolfe, in their Chicago apartment. He bathed and dressed as usual, wearing a gray suit jacket, matching pants and vest, shirt, tie, spats and polished black shoes. Though perhaps past his prime at age 33, McGurn’s appearance still could draw comparisons to the fictional 1920s bootlegger Jay Gatsby character in The Great Gatsby.

It was Friday, the day McGurn regularly went to see pals for late-night bowling at a second floor alley on Milwaukee Avenue in northern Chicago. He drove alone to the alley. When he picked up a score sheet, the alley’s owner handed him a Valentine card, addressed to “Jack McGurn,” left by someone. The card showed a drawing of an apparently destitute man and a woman standing behind a “for sale” sign hawking their household goods. The card’s printed message 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 trousas!”

McGurn surely got the joke — a reference to his dire financial straits in the three years since Frank Nitti, his hated rival who took over as boss of the Chicago Outfit from the imprisoned Al Capone in 193l, kicked McGurn out of the gang and its rackets. However, he may have missed the card’s other, more sinister implication, coming on the seventh anniversary of the St. Valentine’s Day Massacre, the 1929 gangland killing of seven men from George “Bugs” Moran’s North Side Gang for which prosecutors initially charged McGurn but had to drop the case for lack of evidence.

McGurn placed the card on a bench. It was now about 1 a.m., February 15. McGurn and two of his friends were bowling a frame. Suddenly three hitmen who had followed McGurn upstairs burst forward, drew handguns from their overcoats and fired at the unarmed McGurn, striking him in the head and back. He died almost instantly. The assassins calmly left the alley. Patrons evacuated the place, including McGurn’s two friends, who took the score sheet with them to prevent police from learning their names.

McGurn, Capone’s favorite hitman in the 1920s, for all intents made himself into a target for his one-time gang associates. The men believed to have shot McGurn on Nitti’s orders included Claude Maddox and Jack White. In the months before the 1936 shooting, McGurn by some accounts threatened Nitti if he didn’t allow him back into the rackets. Perhaps Nitti instructed his henchmen to deliver the Valentine’s card so that police might think associates of the Moran gang did McGurn in.

Which brings up a point of contention about McGurn’s place in Mob history. Historians and crime writers offer varying accounts of his life. Many over the years have named him the mastermind of the St. Valentine’s Day Massacre — the most infamous Mob hit in America’s gangland past. Some have downplayed his role in it. But for sure, leading up to 1929, he carried a grudge against the Moran gang, which tried but failed to kill him in March and April of 1928. McGurn, months before the massacre, may have convinced Capone to approve his elaborate scheme to entrap and eliminate Moran and anyone snared with him.

Certainly, by the 1929 massacre, McGurn’s reputation as Chicago’s most notorious hitman was such that when almost any gang murder occurred in the city, police considered him a suspect. He well deserved that status. Capone relied on him to commit Outfit rubouts as needed in the mid- to late-1920s. McGurn himself killed about 22 people for Capone — including the public hit on North Side boss Hymie Weiss. Add to that, earlier in the 1920s, McGurn hunted and killed several members of Chicago’s Genna gang whom McGurn held responsible for the fatal shooting of McGurn’s stepfather, Angelo DeMora.

Revenge motive

McGurn was born Vincenzo Gibaldi in Sicily in 1902 or 1903, and as an infant he immigrated with his family to Brooklyn, New York. By most accounts, McGurn’s chosen profession grew out of a desire for revenge against the Gennas who killed DeMora. Some writers, with less plausibility, claim that his resentment started earlier, when he was a boy, after he heard about the shooting death in Brooklyn of his biological father, Tommaso Gibaldi, at the hands the ethnic Irish White Hand gang. The shooters, the story goes, mistook Tommaso for a member of rival Frankie Yale’s gang. Others claim Tommaso died of natural causes and that either McGurn’s mother married DeMora and settled the family in Chicago, or that DeMora merely became McGurn’s foster parent.

In the early 1920s, Angelo DeMora built a grocery business in Chicago’s Little Italy neighborhood and on the side sold sugar to the Genna brothers. The Gennas reigned as local bootleggers who oversaw the resident “alky cookers,” hundreds of small stills making bad hooch at home with the sugar. In 1923, after learning that Angelo also sold sugar to competing bootleggers, the Gennas ordered hitmen to shoot him down.

McGurn, vowing revenge, joined the Genna’s rival crime clan, the high-profile Chicago gang led by Johnny Torrio and Al Capone. Capone hired McGurn and Frank Nitti as his bodyguards. When gangster Joe Aiello put out a $50,000 contact on Capone, the Mob boss gathered information from his paid contacts in Chicago and dispatched McGurn to intercept and hit several of Aiello’s out-of-town would-be hit men.

While still in his teens, McGurn had established himself as an effective amateur boxer in Chicago and, briefly, a professional welterweight. He changed his name to Jack McGurn, specifically “Battling Jack McGurn” for his bouts, thinking he would be more accepted if the public assumed he was Irish. The devoted boxing fan Al Capone likely watched McGurn’s pro fights and may have gone to meet him. After winning his initial three bouts, he suffered a loss and two draws and quit the sport.

McGurn came of age during in the Roaring Twenties, and was an early model for the gangster persona – with his Brooklyn inflection and slang — imitated by leading men in Hollywood films. He evolved into an excellent golfer, expert on the horses, a sharp ukulele player, and dancer extraordinaire in the nightclubs, inveterate womanizer, fit, well dressed and at ease with guns.

By 1926, McGurn had found and killed four Genna men he heard had killed Angelo. With the “Beer Wars” conflict for the liquor business in Chicago in full swing, Capone had McGurn go after the O’Donnell gang for undercutting beer prices. McGurn, armed with a Thompson submachine gun, took part in an attack that killed two O’Donnell members and, to their surprise, a civilian with them — Illinois state’s attorney William McSwiggin, whose death triggered a scandal. Capone, McGurn and Nitti laid low outside Chicago for months, but the carnage drove the O’Donnells out of the beer business.

Target: North Side rivals

Next would be North Side Gang chief Hymie Weiss, whose hitmen had nearly killed Torrio in 1925 (prompting Torrio to retire and hand the mantle of the Outfit to Capone). In 1926, on Capone’s command, McGurn and Nitti formed a hit team to take down Weiss. They waited in a room overlooking the gang’s flower shop hangout once owned by Dean O’Banion, who was gunned down by the Torrio-Capone gang in 1924. As Weiss walked out of the flower shop, McGurn aimed his Thompson through the window and blasted Weiss with a fusillade of .45-caliber bullets. Weiss fell, mortally wounded. McGurn sprayed bullets that also killed “Paddy” Murray and seriously wounded three other prominent North Siders. McGurn, having dispatched the Outfit’s archrival Weiss, was now clearly Capone’s favorite torpedo.

For 1927, McGurn – no doubt on Capone’s orders – set his sights on Jack Zuta, a racketeer and one-time Capone man who left to join new boss Bugs Moran’s North Side Gang. McGurn used bombs thrown from speeding cars to intimidate Zuta, starting a brief tit-for-tat bomb war. Early in 1928, Zuta hired hitman Isadore Goldberg to kill McGurn, but McGurn ambushed and executed Goldberg first. The Moran gang then assigned the heavily armed Gusenberg brothers, Frank and Peter, to get McGurn. The brothers, one with a Thompson, the other a .45 automatic pistol, fired a series of shots that badly wounded McGurn after he entered a smoke shop at the McCormick Hotel. The brothers figured it was the end for McGurn. But, despite being shot in the chest, he survived after surgery in a hospital. McGurn recognized the Gusenbergs as the shooters.

Chicago Police asked him who did it. “Of course I know who shot me,” he declared from his hospital bed, without revealing names. “When I’m well again, I’ll settle this thing myself.”

Less than six weeks later, in April 1928, with McGurn just out of the hospital, the Gusenbergs tried again. They drove up beside his car on a Chicago street and one of them unloaded a Tommy gun at him. As the slugs whizzed by, McGurn leapt from the car for refuge next to a building. The brothers fired more bursts, but their shots missed. McGurn, remarkably unscathed, knew once again who did it.

The Massacre

McGurn stayed hot and determined to make Moran and the North Siders pay. He had time to devise an elaborate but smart plot to liquidate another one of Capone’s nemeses in Chicago. Which brings up the St. Valentine’s Day Massacre, in which the Gusenberg brothers would be among the seven killed. The other Moran gang victims were Albert Weinshenk, Adam Heyer, Albert Kachellek (aka James Clark). Others killed were garage attendant John May and Moran gang hanger-on Dr. Reinhart Schwimmer.

Many historians surmise that McGurn planned the Massacre mission, after convincing Capone that Moran had to go and to deal the North Side Gang a deathblow. Capone made sure to stay clear, leaving town well in advance to vacation at his Palm Island mansion near Miami. McGurn devised a shrewd series of ruses to fool Moran’s gang and any witnesses. He had Capone’s men refurbish a 1927 Cadillac to look like a Chicago police cruiser. McGurn also instructed two of the shooters to don cop uniforms with badges as disguises to make Moran’s men think it was merely a routine raid on known bootleggers.

As the story goes, McGurn had Capone men arrange the sale to Moran of a hijacked load of good Canadian whiskey at a cheap price, then offer a larger hijacked shipment to be delivered early on February 14 to the North Siders’ garage used for bootlegging and meetings, the S.M.C. Cartage Company at 2122 N. Clark Street. (Some observers dispute this as well, claiming that Moran himself said years later that the gang was headed for the garage for a meeting, not to buy whiskey. That begs the question — why would Moran admit to falling for such a ploy that destroyed his gang?)

Capone is said to have had Nitti select the members of McGurn’s hit team, a group known later as Capone’s “American Boys,” from out of town — St. Louis — so that neither Moran’s men nor Chicago Police would recognize them. According to a memo written by FBI Director J. Edgar Hoover in 1936, the men thought to have taken part in the massacre included Fred Goetz, Gus Winkeler, Fred “Killer” Burke, Ray “Crain Neck” Nugent and Robert Carey. Two other men, Bryant Bolton and Jimmy “Swede” Morand, acted as lookouts (one Capone scholar asserts that the lookouts were actually brothers Harry and Phil Keywell) from a rented room across the street from the garage. Bolton and Morand were assigned because they supposedly knew what Bugs Moran looked like. The lookouts were to immediately call a gangster’s home when they observed Moran enter the garage. Then, someone from there would call the Circus Café, owned by Capone’s North Side confederate, Claude Maddox, where the shooters waited, to set the hit scheme into motion.

When the North Siders started arriving on the snow-strewn sidewalks that morning, Bolton and Morand from the distance mistakenly identified gang member Albert Weinshenk as Moran. Moran was late and had not arrived yet.

The plan went into action. The shooters left the café and crowded into the seven-passenger Cadillac modified into a fake police car (some accounts claim a second car was used as well). Once at the garage, the two hitmen in police uniforms and two others in long overcoats entered the garage. Two held Thompson submachine guns (one with a 50-round drum magazine, the other a 20-round vertical “stick” clip) and two with sawed-off shotguns. The hitmen ordered the Moran gangsters to face a brick wall in a line with their hands up.

Since McGurn’s scheme included out-of-town shooters who did not recognize Moran, they probably decided that all the North Siders had to go. Had they missed killing Moran — whom they assumed was among the seven men — Capone may have made them pay with their lives for the blunder. They also could not risk leaving anyone alive as witnesses. Further, the men had been paid handsomely, including allegedly $5,000 to the cold sociopath Burke, to commit the murders. The quartet mercilessly shot down all seven men, killing six and mortally wounding one who died later at a hospital. They left behind 70 shell casings. As part of McGurn’s exit strategy, for witnesses, the two “cops” led the men in overcoats at gunpoint to the car outside as if they were under arrest.

The ‘Blonde Alibi’

Capone’s alibi was that he was out, in public, in Miami, at the time, following a voyage to the Bahamas from February 8 to February 12. McGurn made sure to check into a room at the Stevens Hotel, with his blond girlfriend Louise Rolfe, days before the shooting and to remain there, ordering food and newspapers from room service. Based on his infamy, police set on McGurn right away as a suspect. But Louise swore to police that she was with him in bed — to the point of suggesting they had sex — on the 14th. For her story, the press named the beautiful flapper as McGurn’s “Blonde Alibi.”

Police arrested McGurn anyway, and prosecutors filed charges against him, but weeks later, lacking evidence, they withdrew the case. McGurn’s shrewd operation worked – it decimated Moran’s gang, even though his real target, Moran, missed being killed with the others. While authorities two years later traced two Tommy guns in Burke’s possession to bullets taken from victims, no one was ever convicted in the slayings.

However, the heat from the national uproar from the Massacre would lead to Capone’s downfall, ending with a comprehensive federal tax evasion case that ended in his conviction and an 11-year prison term in 1931. Then the new boss, Nitti, ousted McGurn from the Outfit.

At the time of his death in 1936, McGurn hadn’t killed anyone in years, and was a deeply paranoid, nervous wreck, constantly fearing assassination, even begging Chicago Police to protect him. During his funeral, Capone’s family, unbeknownst to Al, sent a six-foot-tall flower arrangement, with the message “From Al” draped over it, set up next to McGurn’s casket. Imprisoned at Alcatraz, Capone hadn’t even heard yet that his once most favored hitman had died.