10 Infamous Mafia Hits and Assassinations

10 Infamous Mafia Assassinations

Welcome to WatchMojo, and today we’re examining well-known assassinations attributed to the Mafia and other organized crime gangs.

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. Maranzano was made “boss of all bosses” following Masseria’s death, but he too was killed by Luciano, who went on to establish The Commission.

Giuseppe Di Matteo

Santino Di Matteo was a member of the Sicilian Mafia, and this won’t be the last time that he appears on this list. Di Matteo eventually turned informant and ratted out his colleagues, drawing the ire of other powerful Mafioso. They didn’t get to Santino, as he was under intense police protection, but they managed to grab his young son, Giuseppe. Gangsters dressed as police officers kidnapped Giuseppe and kept him prisoner for over two years, subjecting him to brutal conditions. 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 killed.

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.

Giovanni Falcone

Remember how we said we’d return to Santino Di Matteo? Well here we are. His story traces back to 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. Di Matteo took part in this hit and later turned informant, revealing all the details of the assassination.

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.”

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.

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.

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.

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.

The Saint Valentine’s Day Massacre

Speaking of Prohibition, we’ve come to 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.

Do you know of any other infamous gangland stories? Let us know in the comments.