Top 5 Most Notorious Mob Hitmen – HT
They were the enforcers who kept the underworld in line, men who carried out the toughest jobs for America’s most powerful crime families in the streets of New York, Chicago, and beyond. Their reputations were built on loyalty, precision, and fear. Each one had a signature style, a code of silence, and a legacy that still echoes through organized crime history.
This is the story of the top five most notorious mob enforcers, the men who protected empires, silenced threats, and shaped the dark side of the mafia. If you enjoy our videos, don’t forget to subscribe, hit the like button, and share your thoughts about today’s topic in the comments. It really helps the channel grow. Let’s begin.
He was born in Brownsville, Brooklyn, May 10th, 1906. Abraham Reles, son of Galician Jews. His father, Sam, worked the garment trades, then pushed a knish cart when the money ran out. His Hebrew name was Elkanah ben Shimon. He got as far as eighth grade, then the streets finished his education. By 13, the police knew his name.
In 1921, they caught him prying $2 of gum from a vending machine. The court sent him to the Children’s Village in Dobbs Ferry for 4 months. He came home small, quick, and mean. He spent his days in pool rooms and candy stores. He ran with boys who would matter later, Martin “Bugsy” Goldstein and Harry “Pittsburgh Phil” Strauss.
He learned how to collect, how to hurt, and how to live without fear. Prohibition cracked New York wide open. Reles and Goldstein went to work for the Shapiro brothers, Meyer and Irving, who ran parts of Brooklyn. They did errands. They stole. They learned the rackets. The Shapiros never looked after them. The resentment never cooled.
He built his own lane with slot machines. He brought in George DeFeo, and through him made a deal with Meyer Lansky. Lansky wanted Brownsville, East New York, Ocean Hill. Reles wanted backing. They both got what they wanted. With Goldstein and Strauss, he added loan sharking, craps, and labor slugging in the restaurant union.
The money climbed, so did the danger. The Shapiros struck first. A tip lured Reles, Goldstein, and DeFeo into an ambush. They were shot up, but crawled out alive. Meyer Shapiro then dragged Reles’s girlfriend to an open lot, beat her, and raped her. From that moment, the feud was murder. He answered with killers who liked the work, Frank “Dasher” Abbandando and Harry “Happy” Maione.
The tit-for-tat lasted months, then it ended on pavement. Reles pulled Irving Shapiro out of a hallway and into the street and shot him again and again. Two months later, he found Meyer Shapiro on the sidewalk and put a bullet in his face. William Shapiro came last. They beat him to the edge of death, stuffed him in a sack, drove to Canarsie, and started to bury him.
A passerby spooked them off. When the police dug the grave, the autopsy said William had been buried alive. By then, “Kid Twist” was the name people used, a nod to Max Zweifach before him. The new Kid Twist stood just over 5 ft with a lispy snarl and a rolling gait that looked like he was trying to shake his shoes off.
He didn’t need size. He carried an ice pick. He favored the ear as a straight route to the brain. He stabbed, strangled, and shot his way into the syndicate’s good graces. He enforced for Murder Inc., the Brownsville arm of the National Crime Syndicate. The work was steady. The price was low. Lepke Buchalter and Albert Anastasia sent orders down through Louis Capone.
Men like Abbandando, Maione, Goldstein, Strauss, Mendy Weiss, Abe “Pretty” Levine, Charles Workman, and Irving “Knadles” Nitzberg did the killing. They were paid like laborers. They produced like contractors. Bodies stacked across the city and beyond. Witnesses, stool pigeons, mistakes. Reles’s temper was legend.
He once beat a car wash man bloody for a smudge on a fender. He shot a parking lot attendant who couldn’t fetch his car fast enough. He and Strauss, with help from Bugsy and Jukey, murdered Puggy Feinstein in Reles’s own house. Before the victim arrived, he woke his sleeping mother-in-law and asked where they kept the rope and the ice pick.
By 1937, he was doing set piece killings on command. George Rudnick was stabbed 50-plus times and cleaved in a Brooklyn garage because somebody whispered, “Informant.” They left a note. “Thanks for the information. Please call on me again. Signed, Thomas Dewey.” It was a joke for the front page. Everything broke in 1940.
Brooklyn detectives tied Reles to murders he couldn’t talk his way around. Sing Sing’s chair was waiting. Sitting in the tombs, he wrote his wife, Rose. She went to Assistant District Attorney Burton Turkus and said she wanted to save her husband. She was pregnant. The deal was simple.
Reles would talk, the DA would listen. Immunity on what he confessed and no promises on what they could prove without him. He sang like a hymnal. He walked Turkus through the Murder Inc. flowchart. He laid Lepke Buchalter into the murder of Joseph Rosen, the Brooklyn candy store owner. Lepke went to the chair in 1944.
He put Louis Capone, Mendy Weiss, Abbandando, Maione, and Harry Strauss into the ground via Sing Sing’s death house. He even damned his childhood friend, Bugsy Goldstein. He connected dots on Dutch Schultz’s killing. He gave O’Dwyer and Turkus a road map to 85 gangland murders. He was the canary. The papers made it famous. One name towered over the rest, Albert Anastasia, the waterfront boss, future Gambino chief.
Reles was set to put him at the center of the murder of longshoreman Pete Panto. A trial based on his testimony was scheduled for November 12th, 1941. The targets were bigger now, so were the risks. They hid Reles in the Half Moon Hotel on Coney Island, room 623. The cops called that corridor the Squealer’s Suite.
Five detectives round the clock, three other ex-hitmen in nearby rooms. The surf outside, fear in the walls. Before dawn on November 12th, 1941, Reles went out the window. He fell four stories and landed on a second-floor roof extension. His spine shattered. He died right there, in the sea air. Inside the room, they found two bedsheets knotted together.
An insulated 4-ft cord tied to the end and fixed to a valve, or meant to be. Scuff marks on the sill matched the soles of his shoes. The screen on the window below had been lowered a few inches. The knot on the wire gave way. The body fell. The tabloids wrote the line the city remembers, the canary who could sing but couldn’t fly.
Nothing about it sat easy. Reles hadn’t pushed for an escape. He kept close to his guards, even in hotel hallways. Rumors came fast. Frank Costello, it was said, raised $100,000 to buy a fall from that window. In 2005, stories surfaced that Detective Charles Burns, one of the guards, had ties to the disappearance of Judge Joseph Force Crater back in 1930.
Back in ’41, the department demoted five of the officers who were supposed to be watching him. In 1951, a grand jury called the death an accident during a botched escape. Officially, that’s where it ended. Unofficially, it never ends. People saw what they wanted to see, a prank gone wrong, a man desperate to see a pregnant wife, a rope to a hidden cash, a job done to keep Albert Anastasia out of a courtroom.
Brooklyn DA William O’Dwyer said three gunmen from California were in New York ready to put a rifle through a window if the chance no matter how you looked at it. He’s buried at Old Mount Carmel Cemetery in Glendale, Queens. The plot is quiet. The city around it is not. Reles helped build Murder Inc., then took it apart from the witness chair.
He made killers of men who never should have held a gun, then sent those same men to the electric chair with a calm voice and a memory like a ledger. On a cold morning at Coney Island, gravity did what the mob and the law both wanted. In a story that could have finished Albert Anastasia, fell six floors and died on a tar roof by the ocean.
He was born in Brooklyn, September 7th, 1940, the fourth of five children in an Italian immigrant family from Formia, a town in the Lazio region of Italy. His father, Anthony DeMeo, drove a laundry truck. His mother, Eleanor, stayed home and raised the children. Roy worked at a neighborhood grocery store through his teens, learning how to cut meat, a skill that would serve him in darker ways later.
He graduated from James Madison High School in 1959, the same year as Bernie Sanders. To most of his classmates, he was quiet, polite. To the streets of Flatlands, he was already lending money at interest. By 22, DeMeo had the instincts of a businessman and the temper of a killer. He started with stolen cars and loan sharking, but his ambition didn’t fit inside small crimes.
In 1966, a Gambino soldier named Anthony “Nino” Gaggi saw potential in him, a butcher’s hands and a banker’s mind, and brought him into the fold. That was the beginning of the DeMeo crew. His first recruit was a kid from Canarsie, 16-year-old Harvey Chris Rosenberg. Rosenberg dealt marijuana at a gas station. DeMayo saw hustle in him.
He fronted him cash, took a cut, and slowly built a network around the boy. A small army of thieves, hijackers, and killers. Joseph and Patrick Testa, Anthony Senter, Richard and Frederick DiNome. Henry Borelli and DeMayo’s cousin Joseph Dracula Guglielmo. Later came men like Vito Arena and Carlo Profeta. Together they became one of the most violent crews in the history of American organized crime.
In 1972, DeMayo joined a Brooklyn credit union. He sat on the board, smiling in a suit while stealing from its reserves. He laundered drug money through the books, financed loan shark operations, and paid off local cops. On paper, he worked for a company called S and C Sportswear.
To his neighbors, he said he sold used cars, but the real money came from the street, from junkyards, garages, and the dark corners of Brooklyn where debt and fear traded hands. He lived in Massapequa Park, Long Island. A wife, three kids, a house with a backyard and a pool. To his neighbors, he was a family man who hosted barbecues.
To the men around him, he was a storm. The first murder tied directly to DeMayo happened in 1973. The victim was Paul Rothenberg, a porn distributor who’d been paying DeMayo and Nino Gaggi protection money. When Rothenberg was subpoenaed by law enforcement, Gaggi gave the order. DeMayo followed him to a Long Island parking lot and shot him twice in the head with a silenced .38.
It was his first taste of the thing that would define him. Two years later, in 1975, he killed again. A young auto shop owner named Andre Katz, who had spoken to prosecutors about stolen cars. DeMayo’s crew lured him in with a woman, abducted him, stabbed him through the heart, and dismembered him in a supermarket meat room in Rockaway Beach.
They compacted his head in a machine used for cardboard boxes. Katz’s leg was found days later by a man walking his dog. It was the first public sign of something new, a way of killing that left nothing behind. They called it the Gemini method. Inside the Gemini Lounge on Flatlands Avenue, DeMayo created his own version of an abattoir.
Victims were brought through a side door into a back apartment, a silenced pistol to the head, a towel wrapped tight to stop the blood, a knife to the heart to keep the blood from pumping. The body dragged to the bathroom, drained, then stripped, laid on plastic sheeting. Arms, legs, and head removed. The remains bagged and boxed.
The boxes driven to the Fountain Avenue landfill and buried under mountains of New York trash. No body, no crime. By the late ’70s, the Gemini Lounge was a neighborhood bar on the outside and a slaughterhouse behind the walls. The smell of bleach was constant. The regulars, some knew, some didn’t, drank beers a few feet away from fresh corpses.
DeMayo’s operations spread beyond murder. He financed pornography, some of it involving minors, and ran a prostitution ring in New Jersey. He dealt cocaine and Colombian marijuana, despite the Gambino family’s rule against drugs. He laundered money through fake companies, hijacked trucks from JFK Airport, and shipped stolen luxury cars overseas.
Each week, the crew moved four to seven vehicles, Cadillacs, Lincolns, Mercedes, out of the city’s ports. As the profits grew, so did the body count. Some said DeMayo personally killed over 200 people. His own men joked that he enjoyed it, that he treated killing like business, efficient and methodical. In 1977, he made a move that would finally earn him his button.
The Gambino family wanted control of the construction rackets on Manhattan’s West Side. The Irish gangs, the Westies, were in the way. DeMayo set up a meeting with Jimmy Coonan, leader of the Westies, and brokered an alliance. The Irish would handle muscle for the Gambinos in exchange for a cut of union work.
It was a deal that brought DeMayo directly into the family’s inner circle. Castellano finally made him a member. But inside the Gemini Lounge, loyalty had a short shelf life. When one of his men, Danny Grillo, fell into debt and started talking too much, DeMayo had him killed and dismembered. When Harvey Rosenberg caused trouble with a Cuban cartel, DeMayo was ordered to eliminate him.
He hesitated. Rosenberg had been like a son to him, but orders were orders. In May 1979, DeMayo shot him in the head inside the Gemini Lounge. The Cubans wanted to see the body, so they left Rosenberg’s corpse in his car for the police to find. That same year, DeMayo killed an innocent college student, a door-to-door salesman named Dominic Ragucci.
The boy had parked outside his house, and DeMayo, paranoid and wired, mistook him for a Cuban assassin. He chased him through the streets of Long Island and shot him dead. When he realized his mistake, he didn’t eat for days. Even killers have cracks. By 1980, the FBI had eyes on him. His car theft empire, the Empire Boulevard operation, shipped hundreds of stolen vehicles each month to Kuwait and Puerto Rico.
It was making millions, but an informant, Vito Arena, got caught in a robbery and flipped. He told investigators everything, the murders, the methods, the names. DeMayo went into hiding that summer. The FBI bugged homes, watched his crew, and waited. By late 1982, rumors spread through the Gambino family that Paul Castellano wanted him dead.
He’d become too reckless, too exposed. The boss couldn’t risk it. Even his mentor, Nino Gaggi, couldn’t protect him. DeMayo sensed it coming. He started carrying a sawed-off shotgun under his coat, sleeping with a pistol beside his bed. His son Albert remembered him pacing the house, eyes hollow, muttering that he was marked for death.
January 10th, 1983, the coldest week of winter. DeMayo put on his overcoat and drove his Cadillac, the one registered to his wife, to a meeting in Brooklyn. Inside the car’s trunk lay a chandelier from his home, something he meant to have repaired. He told his son it was his 17th birthday, but he had business to finish.
He never came home. 10 days later, police found the Cadillac parked in the lot of the Verrazano Boat Club in Sheepshead Bay. The body inside was frozen solid. Seven bullet wounds to the head. His hand was raised, one shot through the palm, a reflex, maybe the last attempt to shield himself. Investigators believed his killers were his own men.
The same crew he’d led through hundreds of murders had done one more for Paul Castellano. Within a few years, the entire DeMayo crew collapsed. Gaggi died in prison. Senter and Joseph Testa got life sentences. Others flipped or vanished or ended up in landfills of their own making. The Gemini Lounge became a storefront church.
The landfill where they buried the bodies turned into parkland. The city covered the stains, but not the memory. Roy DeMayo was the butcher who became the butchered. A man who turned murder into routine, who thought he could build an empire from blood. In the end, the empire buried him, cold, alone, and forgotten inside the trunk of a car he no longer owned.
It started in New Bedford, Massachusetts, a mill town with salt in the air and not much mercy for kids who learned to fight before they could shave. Joseph Charles Barbosa Jr. was born there on September 20th, 1932. Portuguese parents, a father who boxed, a mother who sewed to keep the lights on. Two brothers, Donald and Anthony.
A sister, Ann. School never took. He left before the eighth grade. But languages did. He spoke Portuguese, Italian, and Spanish. He married a Jewish woman, built a family of his own, and settled in Chelsea, Massachusetts, the edge of Boston’s underworld. He tried the ring first, fought as a light heavyweight.
The alias was The Baron. First pro bout on April 18th, 1949 in El Paso. Last on September 23rd, 1961 in Boston. Eight wins, five by knockout. Eight losses, four by knockout. Five draws. He could punch. He could take one, too. And he kept company with men who lived closer to the street than to the gym. Americo Sacramone, Eddie Connors, Joe DeNucci, Anthony Varannis.
Crime pulled harder. At 18 in 1950, Barbosa went to the Massachusetts Correctional Institution Concord. Five-year sentence. In the summer of 1953, he led the prison’s biggest escape in 75 years. Contraband booze, stolen pills, four guards overpowered, two cars, one wild night through Scollay Square, Lynn, and Revere.
It lasted barely a day. He came back in chains. Temper still hot, assaults on guards that fall and winter. Paroled in 1958, he planted himself on Bennington and Brook in East Boston. The corner took his name, Barbosa’s Corner. He built a crew of burglars and stickup men. Joseph W.
Amico, Patrick Fabiano, James Kearns, Arthur Bratsos, Thomas DePrisco, Joseph and Ronald Dermody, Carlton Eaton, Edward Goss, Nicholas Femia. Officially, the Patriarca crime family supervised him through Stephen “the Rifleman” Flemmi. Unofficially, he answered to his own appetites. He was never inducted, he wasn’t Italian, but he was their muscle.
And in the mid-1960s, as Boston’s mob war escalated, he became something else. A contract killer with a reputation that cleared rooms. Men whispered his nickname, “the Animal”. Between 1965 and 1966, enemies fell. Edward McLaughlin, Cornelius “Connie” Hughes, Stevie Hughes. He aligned with the Winter Hill gang because Buddy McLean stood with Vincent “Jimmy” Flemmi, and Barbosa trusted the Flemmi brothers, Vincent and Stephen.
FBI agent H. Paul Rico learned the trust used it. Quiet pressure, quiet offers. By early 1966, the walls shook. A shooting outside his Chelsea home. Threats. He bullied a protected nightclub and stepped on Gennaro “Jerry” Angiulo’s income. The Patriarca organization turned its back. In October 1966, Boston police arrested Barbosa and three others on gun charges in the combat zone. The others posted out.
His bail was set at $100,000. He sat. Bratsos and DePrisco tried to raise his bond. $59,000 scraped together and were executed inside the Nightlife Cafe by soldiers under Ralph “Ralphie” Chong LaMattina of Ilario Zannino’s crew. Their bodies were dumped in South Boston. The message was plain. “You were finished, Joe.” The murders kept coming.
On April 18th, 1967, Joseph Lanzi, the tipster who exposed the Nightlife killings, was murdered by Jerry Angiulo’s men, Carmen Gagliardi, Frank Cottero, and Ben DiCristofaro. In December 1967, Barbosa’s associate Joe Amico was hit. The ground under Barbosa was gone. That summer, inside Walpole on the weapons case, Stephen Flemmi brought news.
The Angiulo brothers had marked him for death. In June 1967, Barbosa flipped. He talked to the FBI, turned informant, then star witness. He entered the new federal experiment called witness protection. The government promised a restaurant and plastic surgery. It never delivered. The cases came fast. June 20th, 1967. Indictments in Providence against Raymond L.S.
Patriarca and Henry Tameleo for conspiracy in the Willie Marfeo murder. August 9th, Gennaro Angiulo accused in the killing of Rocco DeSeglio. October, six men charged in Chelsea for the March 1965 murder of Edward “Teddy” Deegan. Behind the scenes, the cost of talking was high. On January 30th, 1968, a bomb tore off the right leg of his attorney, John E. Fitzgerald.
The government moved Barbosa like contraband. Thatcher Island, Fort Devens, then junior officers quarters at Fort Knox. He walked a German Shepherd with a young military policeman named John Morris, a name that would later stay in the bureau. May 1968, the Deegan trial opened. 50 days later, the jury convicted six.
Peter Limone, Louis Greco, Henry Tameleo, and Ronald Cassesso received death. Joseph Salvati and Wilfred Roy French received life. Barbosa got 1 year, including time served. In March 1969, paroled under the name Joseph Bentley, he relocated to Santa Rosa, California and enrolled in culinary school. In the summer of 1970, he murdered Clay Wilson.
The FBI counted it as his 26th killing. In 1971, he pled guilty to second-degree murder and took 5 years at Folsom. In his cell, he wrote poems about the Boston wars. Outside, the truth began to loosen its gag. Years later, the Deegan case unravelled. Winter Hill enforcer John Martorano flipped in 1999 and said Barbosa had lied.
Vincent “Jimmy” Flemmi had confessed to killing Deegan. The men Barbosa helped convict, Greco, Tameleo, Salvati, Limone, became names in a government scandal. Two died in prison, two walked free decades later. In 2007, a federal judge in Boston found that the FBI had helped secure the wrongful convictions and ordered $100 million in damages to the four men and their families.
By then, Barbosa was long gone. On October 30th, 1975, he was released again. New name, Joseph Donati. Taken from South Boston twins Richard and Robert Donati, he rented a $250 a month apartment in San Francisco. He made a friend, small-time hustler James Chalmas. The friendship killed him. Word of his hideout reached underboss Gennaro Angiulo. February 11th, 1976.
Barbosa walked out of Chalmas’ place toward his car. A Colt .38 on him. No chance to draw. Four shotgun blasts at close range. He died in the street. Attorney F. Lee Bailey said the quiet part out loud. “With all due respect to my former client, I don’t think society has suffered a great loss.” Later, on a hidden microphone, Ilario Zannino boasted that J.R.
Russo pulled the trigger. “A genius with a carbine,” he said. Barbosa was buried in South Dartmouth Cemetery, Dartmouth, Massachusetts. This is what the record shows. A mill town kid became a boxer, then a killer. A killer became a federal witness. A witness made himself valuable and then made himself useful to lies.
In 1968, six men were convicted on his word. By 2007, a court called those convictions a government-made tragedy. Joseph “the Animal” Barbosa lived by violence, survived by betrayal, and died by a shotgun on a California sidewalk. A life that left blood on the street and a stain on the case files meant to clean it up.
He was born Vincenzo Antonio Gibaldi in Licata, Sicily on July 2nd, 1902. Four years later, he crossed the Atlantic with his mother, Giuseppina Verdurame. Ellis Island stamped them through on November 24th, 1906. Brooklyn took them in. Public School 46 on Union Street. Red Hook streets rough and hungry.
Chicago came calling when he was 14. Little Italy. Taylor Street. He laced up gloves, took fights, and took a new name, “Battling Jack McGurn”, because Irish names sold tickets. His father, Tommaso, died young. His mother married a grocer, Angelo DeMori. Angelo sold sugar on the side to the Genna brothers, kings of the neighborhood stills.
In 1923, the Gennas had DeMori shot. The boy from Licata never forgot. February 1926, McGurn went hunting. Three men tied to Angelo’s murder died inside 8 days. Blood for blood. He drifted through the North Side gang, then by April 1926, he landed where the money and the power were, Al Capone’s outfit. It didn’t take long to learn what he could do.
April 27th, 1926, a car on a Chicago street lit up with gunfire. James J. Doherty and Thomas “Red” Duffy from the West Side O’Donnells died where they sat. Assistant State’s Attorney William H. McSwiggin, riding with them, died, too. Wrong place, wrong time. Slugs matched a Thompson submachine gun McGurn liked to carry. Chicago noticed.
October 11th, 1926, outside Holy Name Cathedral, North Side boss Earl “Hymie” Weiss stepped into the open. A window across the way rattled and McGurn’s Tommy gun answered the prayer. Weiss dropped. Paddy Murray died, too. The Outfit’s war tilted. Joe Aiello tried to buy a new future in 1927. $25,000 bounties on Capone and Unione Siciliana boss Tony Lombardo.
Gunmen rolled in from out of town. Between May and September, McGurn met them at train platforms, on sidewalks, in alleys. At least four never left the city. He took a piece of a speakeasy, the Green Mill at 4802 North Broadway, smack in Bugs Moran’s territory. In November 1927, the club’s manager, Danny Cohen, told him singer Joe E.
Lewis was jumping to the new Rendezvous Cafe on North Clark and Diversey. McGurn made a house call. He slit Lewis’ throat and sliced part of his tongue. Lewis lived, his voice didn’t. He turned to comedy. The room kept selling drinks. The North Siders struck back. March 7th, 1928, Peter and Frank Gusenberg shot McGurn in the lobby of the Hotel McCormick and Ontario and Rush.
He survived. April 17th, James Clark and Billy DeVern ambushed him at Morgan and Harrison. Weeks later, DeVern turned up dead. Score settled for a while. People would talk for the next century about February 14th, 1929. The Saint Valentine’s Day Massacre. Seven men lined against a brick wall in the SMC Cartage garage on North Clark Street.
Two cops with Thompson guns, a fake police car rolling away clean. Prosecutors charged McGurn. He never faced a jury. His blonde alibi, Louise Rolfe, the girlfriend who would become his wife, swore he’d spent the day with her at the Stevens Hotel. No trial, no verdict, only whispers. Did he plan it? Some said yes. Out-of-towners with clean faces and cold hands, Fred Killer Burke, Gus Winkler, Fred Goetz, Ray Crane Neck Nugent, Robert Carey were named later in Bureau memos.
Lookouts across the street, Bryant Bolton and Jimmy Swede Moran, or maybe the Keywell brothers mistook Albert Weinshank for George Bugs Moran. The guns didn’t make the same mistake twice. McGurn kept his mouth shut and stayed in the wind. April 1930, the Chicago Crime Commission printed a list, 28 men poisoning the city. Frank J.
Lush put McGurn at number four. The ink made him famous and useless. The Outfit pushed him out. He took his hands and his nerves to golf. Evergreen Golf Course at 91st and Western. A silent partner, a regular on the tees, a hustler in the clubhouse. People said he kept a machine gun in his golf bag. Bing Crosby, the singer with the easy swing, played rounds with him when he came through town.
August 25th, 1933, the Western Open at Olympia Fields. He entered as Vincent Gebhardi, a nod to his old name. Shot 83 the first day. The second day he had a better rhythm going until two sergeants, a lieutenant, and five highway cops stepped onto the seventh green. A criminal reputation warrants. He asked to finish the round. They let him.
He posted an 86 and missed the cut. They took him off the course instead. By 1936, the money was gone. The friends were gone. The fear stayed. February 14th came around again, 7 years to the day after the massacre. He overslept with Louise in their apartment, bathed, gray suit, vest, spats, polished shoes.
He drove to the second floor Avenue Recreation Bowling Alley at 805 North Milwaukee Avenue. Someone had left a card for him at the desk. A Valentine with a taunt. 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.
He bowled a frame with two friends. Around February 15th, three men in overcoats walked up fast. Pistols out. Shots to the head and the back. Jack Machine Gun McGurn fell hard and didn’t get up. The shooters strolled out. The friends disappeared with the score sheet. The Valentine stayed behind.
They buried him at Mount Carmel Cemetery in Hillside, Illinois. Louise wore the blonde alibi label a few more years. His half-brother Anthony DeMory swore revenge. I know the guys who killed Jack. On March 2nd, 1936, three masked men shot DeMory dead in a Chicago pool hall. The police drew a straight line between both bodies and moved on.
Who ordered McGurn’s end? Take your pick. Bugs Moran had reasons of his own. Frank Nitti’s Outfit had a liability they didn’t trust, a drinker with a big mouth and too much history. James Gusenberg had a brother, Frank, who died on that garage floor in 1929. Claude Maddox and Jack White have come up in whispers as triggermen for Nitti.
No jury ever heard the evidence. No one ever wore the cuffs. His record, 20 plus murders for Capone in the middle years of prohibition. [ __ ] Weiss outside Holy Name on October 11th, 1926. The O’Donnell hit that killed William McSwiggin on April 27th, 1926. The Green Mill address etched into the city’s memory.
4802 North Broadway. Joe E. Lewis and the blade. A fake police car on North Clark. A Valentine on a bowling alley floor. Jack McGurn believed revenge could build a future. For a while, it did. Then the city did what it always does. It paid him in full and left nothing on the table but a poem, a wound, and a name people still say when they talk about how Chicago learned the price of power in the age of booze and gunfire.
He was born in San Giuseppe Jato, a quiet town tucked in the hills outside Palermo. February the 20th, 1957. Giovanni Brusca, the son of a mafia patriarch and the heir to a blood-soaked tradition. His father, Bernardo Brusca, ruled that corner of Sicily under the shadow of the Corleonesi clan.
Men like Toto Riina, Bernardo Provenzano, and Leoluca Bagarella. When his father went to prison in 1985, Giovanni took control of the family. He was 28, violent, and feared. Inside the organization, they called him U Veru, the pig. Others said U Scanna Cristiani, the people slayer. He looked the part, heavy, unshaven, and careless with the eyes of someone who had seen too much and enjoyed too little.
Even other mobsters stayed cautious around him. Tommaso Buscetta, one of the first major informants, once said Brusca was a wild stallion but a great leader. By the early 1990s, the mafia was under siege. Judge Giovanni Falcone had become the state’s most powerful weapon, leading investigations that tore through Cosa Nostra’s ranks.
For Toto Riina, Falcone was an enemy who needed to disappear. He chose Brusca to make it happen. In the spring of 1992, Brusca and his men dug a tunnel under the A29 motorway near the town of Capaci. They filled it with half a ton of explosives. On the evening of May 23rd, Brusca waited on a hill overlooking the road.
Falcone’s plane had landed and his motorcade was heading toward Palermo. A car trailing behind Falcone’s sent a signal. Brusca raised a small remote, a rewired gate opener, and pressed the button. The earth split open. The blast tore a crater into the highway a quarter mile long. Giovanni Falcone, his wife Francesca Morvillo, and three bodyguards were killed instantly.
The explosion shattered glass miles away. Italy stood still. It wasn’t a killing, it was a declaration of war. In the months that followed, the violence spread. Riina’s faction turned to bombs again, this time in Florence, Milan, and Rome. They targeted art galleries, churches, and tourists. 10 people died, 70 were wounded. The message was clear.
If the state struck the mafia, the mafia would strike Italy itself. But the most vicious act of all wasn’t against a judge or a politician, it was against a child. Santino Di Matteo, one of Brusca’s men, had been arrested and turned in former. In revenge, Brusca ordered his son, Giuseppe, kidnapped. November 23rd, 1993, men dressed as police officers came to the boy’s stable, told him his father wanted to see him, and took him away.
He was 11 years old. They kept him alive for 779 days, moving him from place to place, feeding him scraps, and beating him. On January 11th, 1996, Brusca gave the order. The boy was strangled and his body dissolved in acid. It was the kind of cruelty that silenced even hardened killers. When Di Matteo later faced Brusca in court, he broke down in tears, shouting that if left alone for 2 minutes, he would cut off his head.
Brusca’s downfall came a few months later. On May 20th, 1996, police found him in a small house near Agrigento. He was sitting down to dinner with his girlfriend, his son, and his brother, Vincenzo. On the television, a movie about Giovanni Falcone’s death was playing. They arrested him without a fight. When officers brought him into Palermo’s police station, they cheered.
Some tore off their masks, no longer afraid. One officer slipped through the crowd and punched him in the face. In custody, Brusca did what his father never did. He talked. He told investigators about killings, bombings, secret meetings. He confessed to detonating the bomb at Capaci. He named men who’d built it, who’d driven the cars, who’d ordered the hits.
At first, prosecutors thought he was lying to save himself, but piece by piece, the stories matched the evidence. He claimed that Toto Riina’s capture in 1993 wasn’t luck, that Bernardo Provenzano had sold him out in exchange for Riina’s hidden archive of blackmail material. He even suggested that Riina had tried to negotiate with government officials after Falcone’s death, a claim politicians denied, but one that echoed through courtrooms for years.
In 1999, Brusca was sentenced to 30 years for the murder of young Giuseppe Di Matteo. He received another sentence for the Capaci bombing, 26 years instead of life, reduced for his cooperation. Later, another life sentence came for other killings, but the math of justice was cruel.
He would still walk free one day. He spent decades in Rebibbia prison in Rome. Over time, he asked for leniency, visits, furloughs, and finally house arrest. Each request reopened old wounds for the families of his victims. Still, the law treated him as a collaborator, and his time was counted accordingly. On May 31st, 2021, Giovanni Brusca was released from prison.
45 days before the end of his term, he walked out a free man under parole. Politicians called it shameful. The families of Falcone and Di Matteo called it a betrayal. But, the law had spoken. 4 years later, on June 4th, 2025, Brusca’s parole ended. He was done. A man who once claimed to have killed between 100 and 200 people was free to walk the streets again.
The land that once belonged to his family no longer does. The state seized it and gave it to a cooperative named after Placido Rizzotto, a union leader killed by the mafia in 1948. On that same soil, wheat grows, wine is made, and tourists come to stay at what used to be the Brusca farmhouse. Giovanni Brusca will forever be remembered as the pig, the butcher of San Giuseppe Jato, a man who murdered for power and later traded truth for mercy.
His crimes left scars across Sicily, but his name became something else, a reminder of how far evil can go when fear controls a country, and how justice, no matter how delayed, always leaves a mark. [Music]