20 Most Gruesome Mafia Murders


The mafia, a shadowy and enigmatic underworld, has long been synonymous with violence and ruthlessness. In the clandestine world of organized crime, power struggles, territorial disputes, and treacherous alliances were often settled in a blood-soaked fashion.

The mafia’s history is marred by countless brutal murders that are a testimony to the ferocious nature of these criminal organizations.

From the streets of New York to the alleys of Sicily, mafia mobsters have etched their names into history as some of the most ruthless and cunning criminals to ever walk the earth.

This article delves into this dark section of the world and unearths 20 of the most gruesome mafia murders.

These include acts of savagery that not only claimed the lives of rival gang members and their families but sometimes extended their bloody reach to law enforcement officers and even innocent civilians

1. Saint Valentine’s Day Massacre

Arnie Papp, CC BY 2.0, via Wikimedia Commons

The St. Valentine’s Day Massacre was a gruesome mafia murder that took place on February 14, 1929, in Chicago, Illinois. Seven men were killed in the massacre, which was ordered by Al Capone, the boss of the Chicago Outfit.

The victims of the massacre, most of whom were members of the North Side Gang were:

  1. Frank Gusenberg
  2. John May
  3. Joe Adonis
  4. Albert Weinshank
  5. George Moran
  6. Pete Gusenberg
  7. Frank Rio

The victims were lined up against a wall and shot to death by machine gun fire. The massacre was believed to be a retaliation for the attempted murder of Capone’s top enforcer, Jack “Machine Gun” McGurn.

Another reason may be the supposed hijacking of some expensive whisky being illegally smuggled by Capone’s gang from Canada via the Detroit River.

The St. Valentine’s Day Massacre was one of the most notorious crimes in American history. It was a sign of Capone’s power and ruthlessness, and it helped to solidify his position as the most powerful mobster in the United States during that era.

2. Paul Castellano

Castellano’s Mug Shot, Wikimedia Commons

Paul Castellano, the then-boss of the Gambino crime family, was murdered on December 16, 1985, outside of Sparks Steakhouse in Manhattan. The murder was ordered by John Gotti, who was unhappy with Castellano’s leadership and wanted to take over as boss of the Gambino crime family.

Castellano was shot and killed by three gunmen as he was getting out of his car. He was gunned down alongside his underboss Thomas Bilotti outside the steakhouse.

The gunmen were identified as Gotti’s underboss, Salvatore “Sammy the Bull” Gravano, and two other Gambino mobsters, Frank DeCicco and Angelo Ruggiero. The murder also led to a major power struggle within the Gambino crime family, which resulted in the deaths of several other mobsters.

At the time, Gotti was seen as a young and up-and-coming mobster who was more in touch with the modern world. The murder marked the end of the old guard and the beginning of a new era.

3. Anthony John Spilotro “Tony the Ant”

AnthonySpilotro’s FBI Mug Shot, Wikipedia

While Tony’s death was depicted in the 1995 film Casino, his death was far more brutal than what the film claims. The reality was revealed in court following testimony by Mafia enforcer Nick Calabrese.

Spilotro and his brother were murdered on June 14, 1986, following orders by boss Joey Aiuppa after he was sent to prison. Tony and his brother Micheal were lured to a home in suburban Chicago for an event.

What was the event? Micheal was supposed to be made on that day, while Tony was to be promoted. However, on arrival, the brothers would meet their demise.

On arrival, they were led to the basement where a dozen men were waiting for them. Michael was tackled, a rope was placed around his neck, and he was strangled, kicked, and beaten.

Anthony was also beaten and killed before he could say a prayer. The brothers were then buried in an Indiana cornfield where they were found. As per the coroner’s report, they asphyxiated on their own blood, and their bodies were covered from head to toe with bruises and horrific injuries.

4. Giuseppe Di Matteo

Guissepe Di Matte was the 11-year-old son of Santino Di Matteo, a former member of the Sicilian Mafia who later turned informant. As a result of his father becoming an informant, Guissepe was kidnapped by mobsters who pretended to be police officers taking him to his father.

The boy was kept captive for 779 days being mistreated and tortured by the likes of Giovanni Brusca and Gaspare Spatuzza who would narrate the ordeal to the authorities on his arrest.

On 11 January 1996, the boy was finally strangled; his body was subsequently dissolved in a barrel of acid. The act of dissolving a body in acid is known colloquially as the lupara bianca.

The murder of Giuseppe Di Matteo was a message from the Mafia to all informants and traitors. It was a reminder that the Mafia would stop at nothing to protect its secrets and its members.

5. Albert Anselmi, John Scalise and Joseph Giunta

Alberto Anselmi and Giovanni Scalise were some of Al Capone’s best soldiers. The two were rumored to at least have been among the infamous Capone killers on the St. Valentine’s Day Massacre.

However, Capone soon caught wind that the two were plotting against him and he responded with typical savagery. Since Capone was not sure, he set out a trap for them.

Capone fake-slapped one of his men, gangster Frank Rio, and the two attempted to recruit him. In their efforts, it was discovered that Giuseppe “Hop Toad” Giunta was also a conspirator in their plot.

On May 7th, 1929, Capone invited the three to an event at the mob casino in Hammond, Indiana. After toasting and feasting with them, Capone began to rant and rage, claiming he was aware of their plan.

Soon, the three, Scalise, Anselmi, and Giunta were tied into their seats and Capone began beating each of them with a baseball bat. Starting with Anselmi, then Scalise, then Giunta.

After, he had McGurn put three .45 slugs into each man’s head.

6. “Machine Gun” Jack McGurn

Jack McGurn was a notorious gangster and member of Al Capone’s Chicago outfit. He is said to have been involved in some of the most high-profile crimes in the city’s history, including the St. Valentine’s Day Massacre.

McGurn was arrested and charged with murder in the St. Valentine’s Day Massacre, but he was acquitted due to lack of evidence. He continued to work for Capone until the early 1930s when he fell out of favor with the boss.

In 1934, Capone was convicted of income tax evasion and sentenced to 11 years in prison. With Capone gone, he was out of favor in the new regime, even getting shunned by the outfit.

He attempted a career as a golfer, but this did not pan out. On February 15, 1936, “Machine Gun” Jack McGurn was found murdered in a bowling alley on Chicago’s North Side.

This was on the 7th anniversary of the 1929 Valentine’s Day massacre. McGurn was shot severely by three men who stormed the alley and left a note on his body.

The note 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!”

7. Arnold Schuster

Colton Cotton, CC BY-SA 3.0, via Wikimedia Commons

Unlike most names on this list, Arnold was an ordinary civilian. He was a clothing salesman whose attention to detail ultimately got him in trouble.

On a random day in February 1952, Arnols was riding the New York subway from work when he noticed and recognized someone. An amateur detective, he decided to follow the man and subsequently called the police upon realizing the man was a wanted fugitive.

As it turns out, the man was notorious bank robber and prison escapee Willie “The Actor” Sutton who was arrested shortly after the police acted on Arnold’s tip. Soon, Arnold became a local celebrity as his story gained traction in the news.

Sadly, Mafia crime boss Albert “The Mad Hatter” Anastasia happened upon the story and was infuriated. It is worth noting that Albert had no relation whatsoever to Willie Sutton.

He just did not appreciate the attention Albert got for “ratting”. On seeing the news report on Albert, Albert allegedly said, “I can’t stand squealers! Hit that guy!”

In March 1952, “The Mad Hatter” put out a hit on the unsuspecting salesman. On the evening of March 8, 1952, Schuster was returning home from work when he was confronted by a gunman who shot him twice in the groin and once in each eye.

He died on the spot!

8. Angelo Bruno and Antonio Caponigro

The murders of Angelo Bruno also called “Gentle Don” and Antonio Caponigro are a classic case of what goes around come around. The two were members of the Philadelphia crime family in the 70s and early 80s.

Angelo Bruno was the head and Caponigro was his underboss. The “Gentle Don” was just that, Gentle. He had a strong aversion to violence and generally preferred bribery as a negotiating tactic.

It is even said he had previously banished a member of his crew, Nicodemo “Little Nicky” Scarfo, to Atlantic City for being too violent.

However, Caponigro was not so fond of this approach as he felt it limited the gang’s involvement in drug trafficking which reduced their potential profits. Caponigro therefore ordered a hit against his boss Bruno and he was shot in the back of his head in March 1980.

Since the move wasn’t sanctioned by the higher-ups, it was decided Caponigro had to be punished for his greed and disrespecting the hierarchy and procedures of the gang. As it turns out Caponigro was betrayed by his co-conspirator Frank Tieri who he claimed had said the hit on Bruno had been commissioned.

Caponigro was shot on April 18th, 1980 by Joe “Mad Dog” Sullivan while parked outside his Philadelphia home. His body was later found in the trunk of a car in the South Bronx with 14 bullet and knife wounds and roughly $300 stuffed into his mouth and anus to symbolize his greed.

9. Albert Anastasia

ニューヨーク市警察 New York Police Department, Public domain, via Wikimedia Commons

Albert “The Mad Hatter” Anastasia was a ruthless and feared mafia boss who led the Murder, Inc. gang in the 1930s, 1940s, and 1950s. He was known for his unpredictable temper and his willingness to use violence to achieve his goals.

On October 25, 1957, Anastasia was gunned down in a barbershop in Manhattan. It is unclear who ordered the hit but it is claimed to have been ordered by Carlo Gambino, who wanted to take over Anastasia’s territory and become the boss of the Gambino crime family.

Anastasia was shot severely by two men covering their faces with scarves while he relaxed into his barber’s chair. A shocked Anastasia is said to have lunged at the mirror in front of him perhaps looking to escape his attackers.

10. Carmine Galante

New York Police Department, Public domain, via Wikimedia Commons

On July 22, 1979, Carmine Galante, the boss of the Bonanno crime family, was gunned down in a hail of bullets while eating lunch at Joe’s Pizza in Brooklyn. The murder was one of the most gruesome and high-profile mafia killings of all time.

Galante, known as “The Cigar”, due to his smoking habits was a feared and respected figure in the underworld. He had been involved in organized crime since his teenage years, and he had a long and bloody rap sheet.

Galante had been convicted of numerous crimes, including murder, extortion, and racketeering.

In the early 1970s, Galante was released from prison after serving a 10-year sentence for murder. He quickly rose through the ranks of the Bonanno crime family, and he became the boss in 1974.

Galante’s reign as boss of the Bonanno crime family was short and bloody. He was ruthless and ambitious, and he quickly made enemies within the family.

In 1979, a group of Bonanno family members, led by Philip Rastelli, plotted to overthrow Galante. On July 22, 1979, Galante and two of his associates were eating lunch at Joe’s Pizza in Brooklyn when they were attacked by three gunmen.

The gunmen opened fire, killing Galante and his associates instantly before fleeing the scene. A final picture of Galante shows a cigar dangling from his mouth when he died.

11. Bugsy Siegel

Bugsy Siegel, one of the most notorious mafia figures in American history, was murdered in his Beverly Hills mansion on June 20, 1947. He was shot in the head by an unknown assailant.

On finding his body, his left eye had blown out of its socket perhaps due to the pressure caused by the bullets.

Siegel was a member of the Jewish-American mafia and was one of the founders of the Las Vegas Strip. He was known for his flamboyant lifestyle and his ruthless business tactics.

Siegel had made many enemies over the years, and his murder is still unsolved to this day. There are many theories about who killed Siegel and why.

Some believe that he was killed by his own associates, who were unhappy with his management of the Flamingo Hotel and Casino. Others believe that he was killed by rival mobsters, such as Meyer Lansky or Lucky Luciano.

12. Salvatore Testa

Federal Bureau of Investigation, Public domain, via Wikimedia Commons

The tale of Salvatore Testa, son of the notorious Philadelphia crime boss Philip “The Chicken Man” Testa, is a particularly interesting one. Salvatore, often referred to as “Salvie,” was a rising star within the Philadelphia crime family.

He was known for his ambition and ruthlessness, qualities that both impressed and unsettled his fellow mobsters. One of these unsettled mobsters was his boss Nicodemo Scarfo.

Worried about his position, Scarfo ordered a hit on Testa. On September 14, 1984, Salvatore Testa met a gruesome end that would be etched in Mafia history forever.

He was brutally murdered, and his body was found in an abandoned lot in Gloucester Township, New Jersey. An interesting part of the murder is that it had been premeditated days earlier through a kiss of death.

At a Philadelphia funeral attended by dozens of Scarfo-related criminals, a lieutenant of Scarfo greeted Testa by shaking his hand and kissing him for an extended time on the lips, a clear signal that Testa was doomed.

13. Joe Gallo

US-amerikanischen Bundesregierung, Public domain, via Wikimedia Commons

Joey Gallo was a notorious American mobster who was murdered on April 7, 1972, at Umberto’s Clam House in Little Italy, Manhattan, New York City.

Gallo was born in Brooklyn, New York, in 1929. He joined the Profaci crime family (later known as the Colombo crime family) in the early 1940s. He quickly rose through the ranks of the family and became a caporegime (captain) by the late 1940s.

In 1957, Gallo was convicted of extortion and sentenced to 10 years in prison. While in prison, he became a vocal critic of Joseph Colombo Sr., the boss of the Colombo crime family.

Gallo believed that Colombo was too corrupt and that he was not in the best interests of the family. After Gallo was released from prison in 1963, he formed his own crime family, known as the Gallo Gang.

This was after Colombo had offered him a peace offering of $1,000 to end the conflict. However, he asked for $100,000 which Colombo declined.

The Gallo Gang went to war with the Colombo crime family, and the two families engaged in a bloody feud that lasted for several years.

In 1971, Gallo was arrested and charged with murder. He was released on bail, but he was placed under house arrest. On April 7, 1972, Gallo was allowed to leave his home to attend his birthday ceremony at Umberto’s Clam House in Manhattan’s Little Italy.

While sitting with his family, sister, wife, daughter, and his bodyguard, at the restaurant, he was ambushed and shot by four gunmen who were later identified as Joseph Colombo Sr.’s men.

14. Joe Masseria

Joe Masseria was one of the most powerful mafia bosses in New York City in the early 20th century. He was known as “The Boss of Bosses” and controlled a large portion of the city’s organized crime activities.

Masseria was born in Sicily in 1886 and immigrated to the United States in 1902. He quickly rose through the ranks of the New York mafia and became one of the most feared bosses in the city. Masseria was involved in a number of criminal activities, including racketeering, prostitution, and bootlegging.

In the late 1920s, Masseria became involved in a power struggle with another mafia boss, Salvatore Maranzano. Maranzano wanted to unify the New York mafia under his control, and he saw Masseria as a threat.

On April 15, 1931, Masseria was murdered in a restaurant in Coney Island. He was shot four times in the back and once in the head. The murder was ordered by Maranzano, and it is said to have been sanctioned by several other mob bosses including Lucky Luciano.

15. Salvatore Maranzano

See page for author, Public domain, via Wikimedia Commons

After taking out Masseria, Salvatore Maranzano quickly inaugurated himself as the “capo di tutti capi” or “boss of all bosses.” However, Charles “Lucky” Luciano had other plans of his own.

On September 10, 1931, four shooters attacked Maranzano at his place of business on Park Avenue in New York City following Luciano’s orders. Eight scared bystanders saw as the men, armed with firearms, shoot Maranzano to death inside his office.

Although Al Capone and numerous other persons were initially suspected of being involved in the murder, most people now believe that Luciano was the true mastermind.

16. Sam Giancana

ebay.com, front of photo, back of photo, Public domain, via Wikimedia Commons

Sam Giancana was one of the most infamous mobsters of the 1960s and leader of the Chicago outfit. In addition to being known for his mob-related escapades, he has also been linked to conspiracy theories regarding the election of former president John F. Kennedy.

However, Giancana would soon lose control of his troops and would move to Mexico to avoid murder. However, he would return to the USA in 1974 to testify on behalf of the CIA concerning the murder of Fidel Castro which he was alleged to have played a part in.

Giancana was murdered in his Oak Park house on June 19, 1975, after only one year of living there. The FBI noted that he had been shot seven times in the head and that this was consistent with a mob killing.

Giancana’s murder was one of the most high-profile mafia murders in history. It remains unsolved to this day, but there are several theories about who killed him and why.

There is a theory that Giancana was killed by the CIA. This is because Giancana was allegedly involved in a number of CIA plots in the 1960s, including the assassination of President John F. Kennedy.

The CIA may have killed Giancana to prevent him from revealing classified information.

17. Giovanni Falcone

Cyril S (reworked), CC BY-SA 4.0, via Wikimedia Commons

While most of the names on this list were mobsters, Falcone was the opposite. Falcone was born in Palermo, Sicily, in 1939.

He studied law at the University of Palermo and became a magistrate in 1964. He quickly gained a reputation for being a fearless and incorruptible judge.

In the 1970s and 1980s, Falcone was instrumental in bringing down several high-profile Mafia families. In 1992, Falcone was assassinated along with his wife, Francesca Morvillo, and three police officers by a bomb placed on a highway near Palermo.

The hit was carried out by Giovanni Brusca on orders by the Sicilian Mafia more so Salvatore Rina, which saw Falcone as a major threat. This was because he was responsible for the incarceration of 19 top bosses including Michele Greco, Giuseppe Marchese, Salvatore Riina, Giuseppe Lucchese, and Bernardo Provenzano.

Falcone’s murder was a major blow to the fight against the Mafia, but it also galvanized public support for the anti-mafia movement. His legacy continues to inspire people around the world to stand up against organized crime.

18. The Eppolito Murders

The Eppolito murders were a double homicide that occurred on March 22, 1992, in Queens, New York City. The victims were two high-ranking “made” members of Gaggi’s crew which was part of the Gambino crime family.

They were James Eppolito and James Eppolito Jr. who were the paternal uncle and cousin, respectively, of New York Police Department (NYPD) detective Louis Eppolito.  Both men were shot to death in Jr.’s car by DeMeo and Gaggi after they accused them of drug dealing to Paul Castellano.

Not impressed by their claims, Castellano gave Gaggi the leeway to deal with them as he pleased. After killing them, Gaggi fled the scene but was arrested thanks to a report by a witness shortly after.

DeMeo managed to escape and killed the witness following Gaggi’s conviction. 

19. Wilfred “Willie Boy” Johnson

Wilfred “Willie Boy” Johnson was a famous American mobster affiliated with the Gambino Crime family. He was an enforcer of the infamous John Gotti.

However, after a few years, Willie was arrested and imprisoned for armed robbery. After his release, he was disappointed to find his family had been abandoned by the mob and this is when the FBI approached him to become an informant.

Disappointed and bitter, he agreed although he never got any financial compensation from the FBI. After 18 whole years as an informant, he would be outed in a public hearing accidentally.

The FBI attempted to convince him to enter the Witness protection program to no avail. On August 29th, 1988, Willie Boy was ambushed by Thomas Pitera and Vincent “Kojak” Giattino, both hitmen for the Bonnano family.

The men ambushed him in his car in front of his home and shot him severely. Johnson was hit once in each thigh, twice in the back, and at least six times in the head. They allegedly did this as a favor to Gotti.

20. Frank DeCicco

Frank DeCicco, also known as “Frankie D” and “Frankie Cheech” was a high-ranking member of the Gambino Crime. He was murdered in Dyker Heights, Brooklyn, when his 1985 Buick Park Avenue was bombed, on April 12, 1986.

The murder was one of the most high-profile mafia hits of the decade and was seen as a sign of the changing landscape of organized crime in New York.

DeCicco was a caporegime in the Gambino, one of the most powerful mafia families in the United States. DeCicco was murdered by the order of Vincent Gigante and Lucchese’s boss Anthony Corallo.

The order was carried out by Victor Amuso and Anthony Casso of the Lucchese family. The hit was supposed to take out both DeCicco and Gotti but he was not present when the bomb detonated.

Anthony Casso would later disclose that they used an improvised explosive device (IED).

Each of these chilling tales, shrouded in intrigue and brutality, encapsulates the essence of a world where life is often measured in the pull of a trigger or the swing of a blade.

From the power struggles that tore through rival gangs to the silent assassinations that struck fear into the hearts of witnesses and enemies alike. It is worth that these are only a small sample of the many horrific crimes that have been committed by the mafia over the years.