20 Significant Mafia Hits

19. The Hit That Made John Gotti

Paul “Big Paulie” Castellano (1915-1985) was head of NYC’s Gambino crime family from 1976 until his death. The son of a mobster in the Mangano family – forerunner of the Gambinos – who ran a numbers game, Castellano dropped out of school in eighth grade to become a hoodlum. By the 1950s, Castellano had risen to become a capo. Although up to his neck in mob rackets, he acted as if he was a legitimate businessman – an affectation that annoyed many of his hoodlum underlings, who had no delusions about their careers.

The disgruntled underlings included an ambitious capo named John Gotti. When Castellano failed to attend a prominent subordinate’s funeral in 1985, it offended many Gambinos, and disgruntlement soon grew into rebellion. On December 16th, Gotti organized a hit squad, that waited for Castellano’s outside one of his favorite restaurants, Sparks Steak House, in midtown Manhattan. As Castellano was exiting his car, Gotti watched from across the street as the hitmen rushed the mob boss, and gunned him down.

18. Carmine “The Cigar” Galante

Carmine “The Cigar” Galante (1910 – 1979) was a Bonano family boss, who earned his nickname because he was seldom seen without a cigar. Diagnosed as a psychopath by prison psychiatrists while incarcerated in the 1930s, Galante had formed a juvenile street gang in the Lower East Side in his early teens, and became a leading mob enforcer by the time he was twenty. He had a cold dead-eyed stare that scared both gangsters and cops, and by 1940, the NYPD suspected him of involvement in over 80 murders.

Contra the myth that the mafia was anti drugs, the mob were the main importers of narcotics into the US until the rise of the South American cartels. By the 1950s, Galante was a major drug trafficker, which earned him a 20 year sentence in 1962. Released in the mid 1970s, he rose to de facto command of the Bonano family, but his psychopathic ways alienated everybody. On July 12th, 1979, while having an open patio lunch in a Bushwick restaurant, three hitmen, wearing ski masks, walked up to the patio and opened fire with shotguns and pistols, killing Galante and two underlings. He died with a cigar in his mouth.

17. Charles “Cherry Nose” Gioe Stuck His Nose Where It Didn’t Belong

Charles “Cherry Nose” Gioe was a high ranking mobster in the Chicago Outfit. A specialist in extortion and blackmail, he was sent to Des Moines in 1936, to expand the mafia’s activities there. From his base in Iowa, Gioe bankrolled a Hollywood extortion scheme, which shook down studio executives, by threatening them with costly labor strikes and disruptions by a mob controlled union. The racket was eventually busted, and Gioe was convicted of extortion and locked up for four years, before getting paroled in 1947.

In 1954, a fellow Chicago mobster, Joseph “Joey” Glimco, dynamited a Chicago Howard Johnson restaurant then under construction, in a bid to extort the building contractor. When Gioe was asked to intercede on the contractor’s behalf, he foolishly agreed, and totally misreading the situation and the dynamics involved, asked Glimco to “lay off”. On the evening of August 18th, 1954, Gioe left a business meeting and got into his car, but no sooner had he sat down, than another vehicle pulled up, and its occupants opened fire. Gioe was killed instantly, but a bullet to the temple.

16. The Valentine’s Day Massacre

Prohibition fueled organized crime by pouring hitherto unimaginable riches into its coffers. It also fueled a cycle of escalating violence between organized crime factions, competing for a slice of the increasingly lucrative illegal alcohol. In Chicago, that competition reached a crescendo on February 14th, 1929, when seven members of George “Bugs” Moran’s North Side Gang were stood up against a wall, then cut down by automatic weapons gunfire, in what came to be known as the Valentine’s Day Massacre.

Capone had hatched a plan to lure Moran to a warehouse, with the promise of a delivery of cut rate stolen whiskey, then kill him along with his chief lieutenants. Just before reaching the warehouse, Moran spotted a police car nearing the warehouse, and turned around. Four men in police uniforms exited the vehicle, entered the warehouse, and ordered its occupants to line up against a wall for a pat down. The cops were fake, and soon as the men turned around to face the wall, the “policemen” opened fire with shotguns and Thompson submachine guns. Six died on the scene, and a seventh, despite taking 14 bullets, refused to ID the shooters, telling investigators “nobody shot me”, before expiring.

15. Sam Gianca’s Greed Did Him In

Sam Giancana (1908 – 1975) was a Chicago mobster who got his start as Al Capone’s driver, and worked his way up the Chicago Outfit to become one of its highest ranking leaders. He was pals with Frank Sinatra, and had many political ties, including to the Kennedys, whom he reportedly helped by getting JFK into the White House in 1960 with ballot stuffing shenanigans. Conspiracy theorists have long fingered him as a potential culprit in JFK’s assassination, as revenge for what he viewed as ingratitude: rather than cut the mob some slack, Kennedy’s DOJ, headed by his brother Robert, ramped up its investigations of mafia activities.

Giancana was viewed as a loose cannon by his mafia colleagues, for his tendency to attract attention, and as a greedy pig, for his refusal to share in the gambling profits of operations he had set up in Mexico and Iran. After repeated attempts at persuasion failed, a hitman entered his house, evading a police protection detail, and shot him in the back of the head as he was frying sausages. The hitman then turned him over, and shot him six more times in the head and neck.

14. Payback For the Valentine’s Day Massacre

Jack “Machine Gun” McGurn (1902 – 1936) got his nickname because of his love of Thompson submachine guns. He was a Sicilian born small time boxer, who changed his birth name from Vincenzo Gibaldi to the Irish-sounding Jack McGurn, because boxers with Irish names got better bookings back then. Boxing didn’t pan out, so McGurn put more time and effort into his criminal sideline as mob muscle, and by the mid 1920s, he had become one of Al Capone’s chief bodyguards and hitmen. He was a suspect in the 1929 Valentine’s Day Massacre but authorities were unable to charge him for lack of evidence.

Because mob loyalty is largely a myth, Capone and the Chicago Outfit distanced themselves from McGurn, to avoid the heat he drew as a suspect. Cast off, McGurn tried his hand at professional golfing. The results were as dismal as his boxing career, and McGurn fell into poverty. His misery came to an end on February 15th, 1936, one day after the seventh anniversary of the massacre, when three hitmen shot him dead in a Chicago bowling alley. They reportedly left a Valentine’s card near McGurn’s corpse, that 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!”

13. “The Only Man Al Capone Feared”

Polish born Hymie Weiss (1898 – 1926) grew up in Chicago’s North Side, where he took to a life of crime in his early teens. He eventually teamed up with George “Bugs” Moran and Dean O’Banion to form the North Side Gang, which came to dominate crime in north Chicago during Prohibition. Competition with the Chicago Outfit over the illegal alcohol market turned to violent conflict, which claimed the North Side Gang’s boss, O’Banion, in 1924. Weiss succeeded him, and vowed revenge.

He went after the Chicago Outfit’s boss, Johnny Torrio, who came so close to dying in a hit that he resigned, handed the reins to Al Capone, and left for Italy. Capone, who reportedly feared Weiss, tried to make peace, but his offers were rejected. After repeated failed efforts by the rival bosses to kill each other, Weiss led a team of gunmen in 1926, that fired over 1000 bullets into Capone’s headquarters. Capone survived, and a few weeks later, on October 11th, 1926, Weiss was about to enter his headquarters, when a squad of hitmen opened fire from the windows of a nearby second floor building. Weiss was fatally injured, and died in the ambulance en route to the hospital.

12. “The Gentle Don”

Angelo Bruno (1910 – 1980) was a Philadelphia crime boss who became known as “The Gentle Don” because of his penchant for conciliation and trying to resolve conflicts peacefully, which stood in stark contrast to his violent successors. Born in Sicily, Bruno arrived in Philadelphia in his teens, and as a young man, became a close associate of New York’s Gambino crime family. He took part in a variety of rackets, including gambling and moonshining, and by 1959, he had risen to become boss of the Philadelphia crime family – a position he was to hold until his murder, two decades later.

Bruno prohibited his Philadelphia mob underlings from participating in the drug trade, but allowed others to distribute heroin in the city, which infuriated his subordinates. He also angered New York’s crime families by refusing to let them in on the gambling rackets in Atlantic City, a Philadelphia mob monopoly at the time. On March 21st, 1980, Bruno was sitting in his car in front of his home in South Philly, when the back of his head was blasted by a shotgun. His consigliere Antonio Caponigro was suspected of the hit. Because Bruno was murdered without sanction from The Commission, the mob’s supervisory body, Caponigro was himself murdered a few weeks later, and $300 were stuffed in his mouth and up his butt.

11. Bugsy Siegel

Benjamin “Bugsy” Siegel (1906 – 1947) was a Jewish NYC gangster who became a friend and associate of major mafia luminaries such as Charles “Lucky” Luciano, and Meyer Lansky. In 1930, Siegel was a member of a hit team organized by Luciano, which killed NYC’s then-reigning mob boss, Joe Masseria. A feared hitman and one of the original leaders of a contract killing organization that came to be known as Murder Inc., Bugy Siegel also dabbled in bootlegging and gambling, before relocating to the West Coast to expand the mafia rackets there.

While in the West Coast, Siegel raised mafia eyebrows by hobnobbing with Hollywood figures. That was overlooked – for a while – because he helped establish the mafia in Las Vegas, by building the Flamingo Hotel and Casino. Unfortunately for Siegel, he was caught skimming off huge amounts from East Coast mobsters who had invested in Las Vegas. On the evening of June 20th, 1947, Siegel was relaxing in a palatial Beverly Hills mansion, reading the Los Angeles Times, when a hitman riddled him with bullets fired through the window with an M1 rifle, including two shots to the head.

10. Family Betrayal: “Big Jim” Colosimo

Vincenzo “Big Jim” Colosimo was an early 20th century Chicago mobster, who specialized in prostitution, running over 100 whorehouses in the Windy City. When his business was plagued by extortionists trying to shake him down, he called in his wife’s nephew, an NYC gangster named Johnny Torrio, to handle it. Torrio took care of the problem, and stayed in Chicago as Colosimo’s right hand man. Torrio was a criminal visionary, and when Prohibition arrived in 1920, he immediately grasped its potential. He sought to buy shuttered breweries for pennies on the dollar, to operate them illegally and supply the thousands of speakeasies, brothels, and nightclubs in Chicago and the surrounding region

Colosimo rejected the idea, reasoning that doing so would drag him into confrontations with other Chicago mobsters that he would sooner avoid, and decreed that nobody in his organization was to participate in bootlegging. Torrio went ahead and brought the breweries behind his boss’ back, and when Colosimo started getting suspicious, his underling struck first. He informed Colosimo that a shipment was due to arrive at his cafe, and when the boss went to collect it, he was shot in ambush by Frankie Yale, an NYC gangster brought to Chicago specially for the task, on May 11th, 1920.

9. Frankie Yale Discovers That Robbing Al Capone Is a Bad Idea

Frankie Yale (1893 – 1928), the hitman who took out “Big Jim” Colosimo, got his start as a teenager in NYC’s Five Points Gang, where he earned a reputation as a ferocious fighter. By age 19, he had his own protection and extortion racket, which operated out of a Coney Island bar, where Al Capone got his start, working for Yale. From protection rackets, Yale soon branched out into prostitution, running a string of whorehouses. When Prohibition arrived, he got into illegal booze, and became one of Brooklyn’s biggest bootleggers.

Yale and Al Capone were friendly, but things soured in 1927 when Yale got greedy, and started hijacking the Chicago gangster’s trucks. A meeting failed to resolve matters, and Capone set plans in motion for his former boss’ downfall. On July 1st, 1928, Yale received a call that something was wrong with his wife. Refusing to wait for his usual escort of bodyguards, he jumped into his armor-plated car and sped off, only to be intercepted en route by gunmen who riddled his car and shot him to death with armor-piercing bullets.

8. The Failed Hit That Made Al Capone Chicago’s Boss

After seeing to the rubbing out of “Big Jim” Colosimo, Johnny Torrio took over his deceased relative’s criminal empire, and built it into what became the Chicago Outfit. Within a few years, Torrio was the city’s biggest mobster, and its most powerful criminal kingpin, with Al Capone as his chief underling. As the Outfit expanded its operations from its base in Chicago’s South Side, it came into conflict with the Irish-American North Side Gang. After initial attempts at peaceful coexistence failed, Torrio ordered the murder of North Side boss Dean O’Banion in November, 1924, sparking a bloody gang war.

North Side gangsters responded by ambushing Torrio outside his apartment with a fusillade of gunfire. He miraculously survived, despite taking bullets to the jaw, lung, abdomen, groin, and legs. Severely wounded, Torrio was spared from a finishing shot to the skull when the killer’s gun jammed. The near death experience frightened Torrio, and convinced him to get out while he still could. In 1925, he handed control of the Chicago Outfit to Al Capone, and moved to Italy.

7. Joe “The Boss” Masseria

Joe Masseria (1887 – 1931) fled Sicily as a teenager in 1903 to escape a murder indictment, and emigrated to America, which had no extradition treaty with Italy at the time. He became an enforcer for an NYC gang, worked his way up to gang boss, and by the mid 1920s, had become one of the city’s biggest criminal kingpins. Prohibition and illegal alcohol boosted his career, and by 1929, he was the Big Apple’s biggest crime boss. He founded what became today’s Genovese crime family, and dominated NYC’s criminal world until his death in 1931.

In early 1930, rivalry with a rising competitor, Salvatore Maranzano, erupted into a gang war. In the ensuing bloodletting, which came to be known as the Castellamarese War, over 60 mafiosi were slaughtered. The conflict finally ended when Masseria was betrayed by his own men after they cut a deal with his rival, Maranzano. On April 15th, 1931, Masseria was dining and playing cards with his chief lieutenant, Charles “Lucky” Luciano, at a restaurant, when the latter excused himself to go to the bathroom. Then, a hit squad that included future crime bosses Vito Genovese, Bugsy Seigel, and Albert Anastasia, burst into the restaurant, and shot Masseria dead.

6. The Last “Boss of All Bosses”

Salvatore Maranzano (1886 – 1931), of Castellamare, Sicily, founded what became the Bonano crime family, and instigated the Castellamarese War against Joe Masseria for control of New York’s criminal world. After winning that war, he reorganized the American mafia, setting up a basic hierarchical structure that survives to this day. Each established family would henceforth have a boss and underboss, and beneath them would be caporegimes, or captains, in command of soldiers. Above them all, Maranzano declared himself capo di tutti capi, or Boss of All Bosses – the last such occurrence in the American mafia’s history.

Maranazano, was an egomaniac with delusions of grandeur, who fancied himself a Julius Caesar of crime. When he tried to impose Italian mafia customs upon American mobsters raised in the US, it backfired. Five months after Maranzano declared himself capo di tutti capi, Lucky Luciano arranged for four mobsters to visit his office on September 10th, 1931, posing as tax men. They disarmed Maranzano’s guards, then shot and stabbed him to death. After that hit, Luciano abolished the Boss of All Bosses title, and set up a collective mafia leadership council, The Commission, to avoid future gang wars.

5. Murder Inc. and Dutch Schultz

After the deaths of Joe Masseria and Salvatore Maranzano, Lucky Luciano set up a cooperative entity, The Commission, to run the Italian-America mafia and arbitrate its disputes. To give The Commission teeth, Luciano set up a streamlined contract killing organization that came to be known as Murder Incorporated. Headed by Louis “Lepke” Buchalter, Murder Inc. acted as the muscle and enforcers of the mafia’s higher ups. In theory, mob killings had to be preapproved by The Commission, who would then task Murder Inc. with carrying out the murders. Their most famous victim was Dutch Schultz.

Schultz was close friends with many mob higher ups, including Lucky Luciano, but he threatened to become a loose cannon after crusading prosecutor Thomas Dewey put him in his crosshairs. Schultz sought permission from The Commission to kill Dewey, but was turned down – the mob had a strict policy against targeting law enforcement. When Schultz gave signs that he might go rogue and kill Dewey anyhow, The Commission ordered his death before he invited a catastrophic backlash upon all, by murdering the prominent prosecutor. Three Murder Inc. hitmen tracked Schultz down to The Palace Chop restaurant in Newark, New Jersey, where they executed him, his accountant, and two bodyguards.

4. Murder Inc. and Harry Millman

Another major hit carried out by Murder Inc. claimed Harry Millman, a problematic Detroit gangster, in November, 1937. Millman was a bootlegger who stirred trouble with vendettas against members of his own and competing gangs. His behavior was bad for business, and the locals repeatedly tried to do him in, but failed – including a car bomb that killed an unfortunate valet attendant, but spared Millman. Finally, The Commission got involved. A call was made to Murder Inc., and it sent two killers, Harry Strauss and Harry Maione, to Detroit.

Upon arrival, the duo began planning the hit. It was simplified by the fact that Millman was a known drunkard, who spent a lot of time at a few favored bars. Maione and Strauss picked the most suitable bar for their hit, and planned out their entrance and exit and escape routes. Then they simply walked into the bar, and started shooting. After killing Millman, the duo made their escape, and were on a train back to NYC before their victim’s corpse had turned cold. Although there had been numerous eyewitnesses, the hitmen were out of towners unknown to any locals, so nobody was able to identify them.

3. Kid Twist: The Canary Who Couldn’t Fly

Abe “Kid Twist” Reles was a Lower East Side gangster, who ended up as one of Murder Incorporated’s leading hitmen. In 1940, he was implicated in the killing of a minor gangster, and to save himself, he agreed to spill the beans and testify against his colleagues in over 200 murders. It was the first inkling the authorities had of the streamlined contract killing machine’s existence, which by then had carried out over 1000 hits, and it led to the unraveling of Murder Incorporated. Reles turned out to be a savant, with a freakish photographic memory that allowed him to testify in detail about every murder he had been involved in or heard of, including dates, participants, where the killings had taken place, and how they had been carried out.

Once Reles started singing, four other Murder Inc. hitmen turned state’s evidence, and joined him in testifying against their former colleagues. They and Reles were stashed by the authorities in the Half Moon Hotel in Coney Island. Early in the morning of November 12th, 1941, with police guarding the door, Reles fell out of his sixth floor room’s window. Police explained it as an accidental death, but it was clear that the mob had gotten to his police bodyguards, and that one or more of them had pushed him out. As one mobster put it: “The canary could sing, but he couldn’t fly“.

2. The Execution of the “Lord High Executioner”

Albert Anastasia (1902 – 1957) was Murder Incorporated’s second in command, second only to Lepke Buchalter. He rose to head the entire operation in 1936, when Buchalter had to go on the lam. Unlike Buchalter, who had kept a low profile, Anastasia enjoyed letting everybody know that he was a vicious murderer. He took such joy in his duties with Murder Inc. that he became the most feared mobster of his era, earning the nicknames “Lord High Executioner” and “The Mad Hatter”.

He survived Murder Incorporated’s unraveling when the chief witness against him, Abe Reles, “fell” to his death from a 6th floor window just before he was scheduled to testify against Anastasia. He went on to found the Gambino crime family, until karma belatedly caught up with him on October 25th, 1957, in the barber shop of NYC’s Park Sheraton Hotel. As the Mad Hatter relaxed in his chair, two assassins, their faces covered with scarves, burst in, shoved the barber out of the way, and riddled Anastasia with bullets.

1. The Most Significant Mob Hit Backfired Horribly on the Mob

Perhaps no single mob hit had a more significant or longer lasting impact on the Italian-American mafia than one that took place on October 15th, 1890, in New Orleans, claiming the life of the city’s police chief. Rival Sicilian crime families had been engaged in a turf war over control of the waterfront, and when the violence spilled over, the citizens clamored for the authorities to do something about it. When the police chief launched an investigation of mafia activities, he was gunned down as he was walking home from work. His last words before expiring were “the Dagoes shot me“. The backlash was immediate, and 19 mobsters were arrested and prosecuted.

In a first trial of 9 of them, the defendants successfully tampered with the jury, and despite overwhelming evidence, 6 were acquitted while the other 3 had hung juries. The following day, March 14th, 1891, a mob numbering in the thousands, including some of New Orleans’ most prominent citizens, stormed into the prison housing the defendants, and lynched 11 of them. It was biggest single mass lynching in American history. It had a salutary effect, by demonstrating to the mob that America was not the Old Country, where criminals could get away with brazen defiance of law and order. In response, the mob adopted strict rules against targeting law enforcement, even preemptively killing mafiosi who threatened to go after cops or prosecutors.

_________________

Where Did We Find This Stuff? Some Sources and Further Reading

American Mafia History – “Machine Gun” Jack McGurn

Am-Pole Eagle – The Man That Al Capone Feared

Encyclopedia Britannica – Jim Colosimo

Biography – Sam Giancana

Crime Magazine, October 14th, 2009 – The Guileless Gangster

Encyclopedia Britannica – Salvatore Maranzano

Gangster Report – The Last Purple: Harry Millman

J Grit – Abe “Kid Twist” Reles, Gangster, Murder Inc.

Mafia History – What Do We Know About Frankie Yale?

Mafia Wiki – Johnny Torrio

Mob Museum – Albert Anastasia

Mob Museum – Who Killed Benjamin “Bugsy” Siegel?

National Crime Syndicate – How Did Joe Masseria Get Killed?

New York History Blog – The Corpse in the Grey Suit

NY Daily News, December 15th, 2015 – Paul Castellano Hit, 30 Years Later

Ozy, October 15th, 2017 – The Heroin Don’s Last Meal

Ranker – Most Violent Mob Hits

Wikipedia – March 14, 1891 New Orleans Lynchings

Wikipedia – Saint Valentine’s Day Massacre