20 Most Infamous Real-Life Mafia Hits and Assassinations

20 Infamous Mafia Hits and Assassinations

Welcome to WatchMojo, and today we’re looking at twenty of the most famous hits orchestrated by the Mafia.

The Saint Valentine’s Day Massacre

We begin with the most famous gangland shooting of all time. On Valentine’s Day 1929, seven men associated with Chicago’s North Side Mob were lined up and shot with tommy guns by four unknown assailants. At the time, the North Side Mob were in a war with Al Capone’s Chicago Outfit, as both vied for control of the city and its bootlegging operations. The shooting became international news and is now synonymous with mob violence. While the murders are officially unsolved, most people assume that the men were killed on Capone’s orders, as he wished to eliminate North Side leader Bugs Moran and his lieutenants. However, Moran was not in attendance at the shooting and lived until 1957.

Joe Masseria

The story of Joe Masseria is full of twists and turns. Masseria led the New York crime family of the same name, with his reign lasting from 1922 to 1931. Seeking absolute control of New York, Masseria battled fellow gangster Salvatore Maranzano in what is known as the Castellammarese War. But in 1931, Masseria’s own lieutenant Lucky Luciano betrayed his boss and brokered a deal with Maranzano, positioning himself as second-in-command. Luciano orchestrated Masseria’s hit, and he was shot to death inside a Coney Island restaurant called Nuova Villa Tammaro. While Maranzano was made “boss of all bosses” following the hit, his time at the top would be short lived.

Salvatore Maranzano

This was basically a corporate restructuring that birthed the modern Mafia. In 1931, after winning the bloody Castellammarese War, Salvatore Maranzano declared himself The Boss of Bosses. But the younger generation, led by the visionary Lucky Luciano, had no interest in serving an old world dictator. On September 10, four hitmen disguised as government tax agents entered Maranzano’s Park Avenue office, disarmed the guards, and assassinated him with knives and guns. His death marked the immediate end of the Mustache Pete era. Luciano subsequently abolished the Boss of Bosses title and established The Commission, a governing body that ensured the Mob would be run like a sustainable business rather than a chaotic feudal kingdom.

Dutch Schultz

Sometimes you are simply too dangerous for your own good. The Dutchman was an unpredictable bootlegger who planned to assassinate U.S. Prosecutor Thomas Dewey. The Commission, fearing the unparalleled federal heat such a high profile murder would bring, decided Schultz was a liability. On October 23, 1935, hitmen from Murder, Inc. burst into the Palace Chophouse in Newark and shot Schultz in the restroom. But he didn’t die right away. Instead, he lingered for hours gripped by a high fever and babbling strange, poetic nonsense. Police stenographers transcribed his delirium, preserving surreal lines like “A boy has never wept… nor dashed a thousand kim.” These haunting final words cemented his demise as one of the most bizarre exits in gangland history.

Bugsy Siegel

One of the most notorious gangsters in American history, Bugsy Siegel was paramount in the development of Las Vegas and its culture of gambling. A prolific bootlegger in New York, Siegel moved out west when Prohibition was abolished in 1933, and he became a genuine celebrity as his cultural reputation increased. However, his Flamingo hotel had a disastrous opening and he quickly fell into debt with the mob. Some even suspected that Siegel was stealing construction money for his own personal profit. A contract was placed on his life, and on June 20, 1947, Siegel was shot by a sniper while reading in his girlfriend’s home. The shooter has never been identified.

Albert Anastasia

A co-founder of the American Mafia, Albert Anastasia ran the organized group Murder, Inc. and what is now the Gambino crime family. He quickly developed a reputation for being ruthless, earning scary nicknames like Lord High Executioner and The One-Man Army. However, his reputation for violence gave Anastasia a number of equally-dangerous enemies, and it all came to a head on October 25, 1957. While getting his hair cut at the Park Sheraton Hotel, two gunmen burst into the shop and shot Anastasia to death. The orders allegedly came from rival crime boss Vito Genovese and Carlo Gambino, who betrayed Anastasia with the latter becoming head of the family.

Joe Gallo

Few hits were as brazen as the slaying of Crazy Joe. A renegade member of the Colombo family, Gallo was a celebrity gangster who hobnobbed with actors and even inspired a Bob Dylan song. However, his open rebellion against the bosses carried a steep price. On April 7, 1972, while celebrating his 43rd birthday at Umberto’s Clam House, gunmen burst in and opened fire. Gallo famously flipped a butcher block table to protect his family before stumbling out into the street to die. The hit remains iconic for its cinematic location, proving that celebrity status couldn’t save you from Mob justice. It was a chaotic, bloody spectacle that forever marked Little Italy’s history and ended the life of the counterculture wiseguy.

Sam Giancana

A powerful mob boss is shot in the back of the head while frying sausage and peppers in his own basement. It’s a scene straight out of a noir thriller. Sam Giancana was the flamboyantly public boss of the Chicago Outfit, possessing ties to Frank Sinatra and the Kennedy administration. But in June 1975, just days before he was scheduled to testify to the Senate regarding CIA and Mafia collaboration, he was silenced permanently with a .22 caliber pistol. The convenient timing of the hit fueled decades of conspiracy theories linking the Mob to the JFK assassination and plots against Fidel Castro. Whether it was the Outfit or the CIA, someone ensured Giancana’s secrets died with him, leaving historians to wonder just how much history was buried that night.

Jimmy Hoffa

Okay, technically this is a “disappearance,” but pretty much everyone knows it: Jimmy Hoffa was murdered. The powerful Teamsters president vanished on July 30, 1975, from the parking lot of the Machus Red Fox restaurant in Michigan. Hoffa was deeply entrenched with the Mob, and his plan to regain control of the Teamsters Union threatened their financial interests. Though his body was never found, sparking widespread rumors of Giants Stadium and Florida swamps, most people now accept that he was killed and cremated. In the eyes of the law, it remains a cold case. But in the eyes of history, it is widely accepted as one of the most successful and disciplined hits in Mafia history.

Danny Greene

Turning Cleveland into “Bomb City, U.S.A.”, Danny Greene was the fearless leader of the Celtic Club who simply refused to die. A charismatic Irish mobster, Greene openly taunted the Italian Mafia, surviving countless assassination attempts ranging from drive-by shootings to building collapses. But his luck finally ran out on October 6, 1977. While leaving a dentist appointment, Greene was killed by a massive car bomb triggered remotely from a nearby parking lot. The explosion was so powerful it rocked the entire neighborhood and ended the life of the “Teflon Irishman.” The subsequent investigation helped topple mob bosses across the country, proving Greene was just as dangerous dead as he was alive.

The Blackfriars Massacre

In the early morning of June 28, 1978, a number of men burst into Boston’s Blackfriars Pub and attacked the occupants, who had been playing a game of backgammon. Five people were killed in the attack, including owner Vincent Solmonte and night manager John Kelly. Their bodies were later discovered by the pub’s janitor. The perpetrators have never been identified, but investigators believe it was a gangland shooting orchestrated by the Irish Mob. They had found trace amounts of illicit substances at the scene, and both Solmonte and Kelly were alleged to have personal connections to the Mob. Some believe that the shooting was orchestrated by Whitey Bulger, the famous gangster popularized in the 2015 film “Black Mass.”

Carmine Galante

Known as The Cigar, Carmine Galante was famous for his smoking habit and served as acting boss of the Bonanno crime family in the late ‘70s. During his tenure, the Bonanno family entered a war with the Gambino family, as each vied for control of New York’s illicit substances market. However, Galante proved too ambitious for his own good, and other crime bosses grew concerned about his brazen violence and unchecked aggression. A contract was placed on Galante by The Commission, and on July 12, 1979, three masked men entered a Brooklyn restaurant and shot Galante. He was killed instantly, with the cigar he was smoking still dangling from his mouth.

Dominick Napolitano

Life isn’t always like the movies, but this hit was the tragic sequel to a Hollywood favorite. “Sonny Black” Napolitano was a powerful Capo in the Bonanno family, best known for unwittingly mentoring FBI agent Donnie Brasco. When Donnie’s true identity was revealed, the Mafia code demanded blood for the security breach. In August 1981, knowing his fate was sealed, Napolitano gave his jewelry to a bartender before heading to a final meeting. Upon arrival, he was shoved down a basement staircase and shot to death. When his body was recovered a year later, his hands had been severed - a symbolic warning to others that he had allowed a rat to shake hands with the brotherhood.

Thomas DeSimone

You may know Thomas DeSimone better as the fictionalized Tommy DeVito, the hot-headed and psychotic gangster played by Joe Pesci in “Goodfellas.” DeVito is modeled after DeSimone, who worked in New York’s Lucchese crime family and partook in a number of murders, including those of William Bentvena and Ronald Jerothe. DeSimone went missing in January of 1979, and most historians believe that he was assassinated. Famous informant Henry Hill claims that DeSimone was killed on the orders of John Gotti and the Gambino crime family in retaliation for the murders of Bentvena and Jerothe.

Roy DeMeo

There are hitmen, and then there are monsters. Roy DeMeo headed a crew for the Gambino family suspected of murdering up to 200 people, often utilizing their horrific “Gemini Method.” This involved luring victims into the Gemini Lounge, shooting them, and immediately draining the body of blood in a bathtub to make disposal easier. DeMeo was so efficient he eventually terrified his own bosses. By 1983, with the FBI circling, Paul Castellano decided the executioner had become a liability. On January 10, DeMeo was found in the trunk of his Cadillac, riddled with bullets. In a chilling final tableau, his body was frozen solid in the fetal position, a defensive gunshot wound on his hand.

Paul Castellano

Between 1976 and 1985, Paul Castellano ran the Gambino crime family, having succeeded Carlo Gambino himself after he died of a heart attack. In 1985, underboss Aniello Dellacroce died of cancer and Castellano failed to attend his wake, infuriating other mafioso. To make matters worse, Castellano then promoted an undeserving mobster named Thomas Bilotti to underboss, further irritating an already-furious group of gangsters. John Gotti and a number of conspirators placed a hit on Castellano, and both he and Bilotti were shot to death outside Sparks Steak House. These two deaths allowed Gotti to take the mantle and become head of the Gambino family.

Tony Spilotro

If you have seen Martin Scorsese’s “Casino,” you know exactly how this one ends. Tony Spilotro was the Chicago Outfit’s main enforcer in Las Vegas, ensuring the skim kept flowing. But as he drew too much heat and defied orders, the bosses back home lost patience. In June 1986, Tony and his brother Michael were lured to a meeting, brutally beaten, and buried in an Indiana cornfield. The 2007 “Family Secrets” trial revealed they were actually beaten to death in a basement in Illinois before being transported to the cornfield. Regardless of the location, it was a gruesome act that signaled the final curtain call for the Outfit’s golden era in Las Vegas.

Angelo Bruno

Known as the Gentle Don, Angelo Bruno ruled the Philadelphia crime family for two decades with a preference for bribery over bullets. However, in the Mob, peace is often just a temporary pause between wars. On March 21, 1980, Bruno was sitting in a car outside his South Philly home when his reign ended with a single shotgun blast behind the right ear. The unauthorized assassination was engineered by his own consigliere, Antonio Caponigro, who foolishly believed the Commission would sanction the coup. Instead, Bruno’s death shattered the stability of the Philadelphia underworld, sparking a bloody, decade-long civil war involving Little Nicky Scarfo that transformed a quiet, profitable empire into a chaotic ruin.

Giovanni Falcone

While the American Mafia underwent these shifts, the Sicilian Mafia faced off against Giovanni Falcone, a tough and brave Italian prosecutor who came down hard on the Mafia. He oversaw the famous Maxi Trial throughout the late ‘80s and early ‘90s, which culminated in 338 convictions and nineteen life sentences given to various bosses. But on May 23, 1992, the Mafia retaliated. They planted nearly 900 pounds of explosives under a bridge and blew them when Falcone drove over it, killing him and a number of others. A member named Santino Di Matteo took part in this hit but later turned informant, triggering a horrific act of revenge against his family.

Giuseppe Di Matteo

Following the Falcone assassination, powerful Mafioso targeted Santino Di Matteo's young son, Giuseppe, in a desperate attempt to silence his father’s testimony. Gangsters dressed as police officers kidnapped Giuseppe and kept him prisoner for over two years, subjecting him to brutal conditions across various locations in Sicily. Santino even came out of hiding and traveled to Sicily in the hopes of rescuing his son, but it was too late. On January 11, 1996 - the 779th day of his imprisonment - Giuseppe was strangled and his body dissolved in acid. The hit remains one of the most tragic and widely condemned acts in the history of organized crime, shattering the Mafia’s “men of honor” myth forever.

Do you find these stories fascinating, or terrifying? Let us know in the comments below!