Chilling Photos Of History’s Most Infamous Mob Hits

Published August 17, 2017
Updated March 14, 2019

Photos from the crime scenes of some of the 20th centuries most brutal murders paints a picture of how organized crime has persisted and flourished throughout history.

Joe Masseria, 1931

Joe Masseria Mob Hits
In 1930, a Sicilian faction led by Salvatore Maranzano waged war against a Sicilian-American group led by Joe Masseria for control of Mafia activity in the United States. Ultimately, in 1931, Masseria allies led by Charles "Lucky" Luciano cooperated with Maranzano and betrayed Masseria in order to end the war. Masseria was shot to death in a Coney Island restaurant, the war ended, and Luciano forged the basic structure of the American Mafia as we know it today.Bettmann/Getty Images

Albert Anastasia, 1957

Albert Anastasia
Detectives take notes and examine the barbershop of New York's Park Sheraton Hotel, where the body of Murder Inc.'s Albert Anastasia lies, partially covered, on the floor after his murder by unknown gunmen. George Silk/The LIFE Picture Collection/Getty Images

The Saint Valentine's Day Massacre, 1929

Valentines Day Mob Hit
On February 14, 1929, seven members of the North Side Gang were trapped in a garage, lined up against the wall, and shot to death by members of Al Capone's rival gang, which was at war with the Irish North Siders for control of Chicago. Bettmann/Getty Images

Carmine Galante, 1979

Carmine Galante Table
The body of Carmine "Lilo" Galante (top right), boss of the Bonanno crime family, lies outside of Joe & Mary's Italian-American Restaurant in Brooklyn. Galante was murdered by some of his own men, acting on orders from a collection of rival mob families upset over Galante's power grabs.Frank Castoral/NY Daily News Archive/Getty Images

Hymie Weiss, 1926

Mob Hits Hymie Weiss
Earl "Hymie" Weiss was the leader of the Chicago North Side Gang and known as the "only person Al Capone feared." Nevertheless, Weiss was killed when Capone's men opened fire with a submachine gun on him and his associates while they were visiting a courthouse where an ally of his was on trial. Chicago History Museum/Getty Images

Dutch Schultz, 1935

Dutch Schultz Mob Hits
Arthur "Dutch Schultz" Flegenheimer, a powerful New York mob boss in the 1920s and '30s, was ultimately killed in Newark, New Jersey by an assassin hired by the Mafia Commission, which opposed his attempts to kill a special prosecutor who was coming after Shultz on racketeering charges.Bettmann/Getty Images

Paul Castellano, 1985

Paul Castellano
The body of Paul Castellano lies covered with a sheet after he was gunned down on a New York City sidewalk. Castellano, the boss of the Gambino crime family in the late 1970s, was killed by a faction within his own family led by John Gotti, who felt Castellano had disrespected the Mafia by focusing on white-collar crime and by not attending the wake of a senior Gambino figure weeks earlier.Ruby Washington/New York Times Co./Getty Images

Thomas Bilotti, 1985

Thomas Bilotti
The body of Thomas Bilotti, underboss to Paul Castellano, lies on the street after he was gunned down alongside Castellano outside Sparks Steakhouse in Manhattan.Bettmann/Getty Images

Frank Decicco, 1986

Frank Decicco's Blown Up Car
Frank DeCicco was a Gambino family underboss in the 1970s and '80s. He was killed by a car bomb in the Bensonhurst section of Brooklyn in 1986. His assassination was revenge for DeCicco's murder of mobsters Thomas Bilotti and Paul Castellano.Anthony Pescatore/NY Daily News Archive/Getty Images

John Dillinger, 1934

John Dillinger
The body of bank robber John Dillinger is put on display in a Chicago morgue after he was shot to death by the FBI and police. Dillinger, one of the most infamous gangsters of the 1920s and '30s, robbed banks across the Midwest with a group that included the likes of "Baby Face" Nelson and Homer Van Meter.Bettmann/Getty Images

Homer Van Meter, 1934

Homer Van Meter
John Dillinger associate and notorious bank robber Homer Van Meter, was killed after fleeing police in St. Paul, Minnesota.Bettmann/Getty Images

"Baby Face" Nelson, 1934

Baby Face Nelson
George "Baby Face" Nelson, known for his daring bank robberies and murders, is said to have killed more FBI agents in the line of duty than any other person. Ultimately, he was killed in 1934 in a gunfight with the FBI.Bettmann/Getty Images

Charles Gioe, 1954

Charles Gioe Car
Charles "Cherry Nose" Gioe, was an associate of Al Capone's notorious for his extortion of movie stars. In the end, Gioe was shot through the head by mafia hitmen hired by a Chicago mob boss whose plans Gioe had unknowingly interfered with. Bettmann/Getty Images

Walter Sage, 1937

Walter Sage
Walter Sage, a hitman and racketeer in the Murder Inc. crime syndicate in the 1930s, was stabbed to death with icepicks by two of his fellow syndicate members, Irving “Big Gangi” Cohen and Jacob “Jack” Drucker while they were driving through New York's Catskill Mountains for skimming money from the organization. They tied his body to a slot machine and threw it into a river.Bettmann/Getty Images

Frankie Yale, 1928

Frankie Yale
Frankie Yale was a Brooklyn mob boss known for being the original employer of Al Capone. He was killed when he was lured away from his club with a cryptic phone call about his wife, then gunned down in his car on the way home. Many people suspect that the hit was ordered by Capone himself.Bettmann/Getty Images

Tony Lombardo, 1928

Tony Lombardo Mob Hits
Antonio "Tony the Scourge" Lombardo, a close associate and consigliere to Al Capone, was gunned down by rival gangsters on the corner of State and Madison Streets in Chicago in retaliation for Capone's supposed involvement in the killing of Frankie Yale.NY Daily News Archive/Getty Images

Jack McGurn, 1936

Jack Mcgurn
Jack "Machine Gun Jack" McGurn was a member of Al Capone's gang, the Chicago Outfit, and was suspected to be one of the people who carried out the St. Valentine's Day Massacre. He was himself murdered in 1936 in a Chicago bowling alley on the anniversary of the attack, likely as revenge for the massacre seven years earlier.Keystone-France/Gamma-Keystone/Getty Images

Harry Millman, 1937

Harry Millman
Powerful Detroit mobster and former "Purple Gang" member, Harry Millman was killed in 1937 at Boesky's, a restaurant-deli in Chicago. He was shot to death by Murder Inc. gunmen hired by the Mafia who he had aggravated with his intense hatred of Italian gangsters.Bettmann/Getty Images

Bugsy Siegel, 1947

Bugsy Siegel Death
Benjamin "Bugsy" Siegel, whose criminal empire essentially created Las Vegas in the 1940s, was a powerful figure in both the Jewish mob and the Italian Mafia. In the end, he was killed by an unknown assailant who shot him through a window with an M1 Carbine while he was staying at an associate's house in Beverly Hills. Bettmann/Getty Images

Joseph Colombo, 1971

Joseph Colombo Lying Dead
Joseph Colombo, boss of the Colombo crime family and the founder of the Italian-American Civil Rights League, was shot in 1971 while on a speakers' platform for an Italian-American Unity Day ceremony in New York. Though the bullet didn't kill him, he was left fully paralyzed and died seven years later in a hospital bed. It remains unclear which rival mob family had ordered the hit.Bettmann/Getty Images

Angelo Bruno, 1980

Angelo Bruno Cops
Philadelphia police carry the body of Angelo "The Gentle Don" Bruno, Philadelphia's organized crime leader in the 1960s and '70s. The 69-year-old mob boss was shot in the back of the head with a shotgun in his car by one of his own associates as part of a power grab.Bettmann/Getty Images

On July 12, 1979, diners were eating at Joe & Mary's Italian-American Restaurant in Bushwick, Brooklyn when three men in ski masks, armed with shotguns and handguns, burst through the front door.

They walked calmly to the sunlit patio, where they opened fire on the patrons who were still in the middle of their meal. Two men were shot in the back of the head and a third received a shotgun blast to the chest that knocked him straight off of his chair and onto the ground. Surprisingly, the blast didn't dislodge his signature cigar from his mouth, and he lay on the ground dead with it still firmly between his teeth.

Two other men sat at the same table, but were left unharmed. The masked men then sprinted off out the back door.

The man who was shot in the chest was once known as "the boss of all bosses," Carmine Galante, the leader of the Bonanno crime family. He was known to most by his nickname, "Lilo," Italian slang for "cigar," because he was never seen without one in his mouth. One of the most feared Mafiosi in New York, this was a man who once said, "No one will ever kill me, they wouldn't dare."

The two other dead men were Galante's associate, Leonard Coppola, as well as the owner of the restaurant and Galante's cousin, Giuseppe Turano.

The two men at the table that were left untouched were the young soldiers in the Bonanno organization that had set Galante up. The killers were also from the Bonanno family, part of a faction led by capo Al Indelicato that sought to kill their boss.

The other Mafia families had become enraged with Galante's brazen power grabs and blatant disrespect. He had amassed a large, highly profitable heroin operation and refused to share his profits with the other families. Finally, the Mafia Commission, the highest rungs of Mafia leadership, ordered a hit on him, and used his own men to do it.

The Galante hit is just one of many like it, yet one more tale of greed, betrayal, violence, and death.

See more of history's most infamous mob hits in the gallery above.

After this look at mob hits of decades past, learn about the most brutal gangs around the world. Then, have a look at these grisly photos of the mafia in the 1980s.

Gabe Paoletti
Gabe is a New York City-based writer and an Editorial Intern at All That Is Interesting.