5 deadliest mafia hitmen in history

Mafia – the word conjures up images of men in suits, wearing hats and sunglasses with weapons in their hands and walking smartly with a swagger not found in ordinary men. Elevated almost to a heroic level in popular culture, especially movies, these ‘dons’ mostly of Italian-American descent have captured the imagination of people all over the world since the 19th century when they became quite well known especially due to the force over their writ in New York city.

The mafia’s main task is the mediation of feuds between criminals and the organization and enforcement of illicit agreements through violent means. Mafias are involved in secondary activities like gambling, loan sharking, trafficking of drugs, prostitution, murder, and cheating.

Mafia murders are some of the grisliest to take place because they are meant to give a message. But only one requirement satiates an actual mafia hitman and that is the payment of his dues. The 5 mafia hitmen which have been enumerated below made their fortunes in their trade and also spent many years mutilating and dismembering their victims. The Murder, Inc. was a subcontractor for the so-called ‘Five Families’ of New York from the 1920s to the 1940s. Mafias and especially their bosses have held a disproportionate amount of power in their ‘families’ or groups as they are known. 

Some of these hitmen enjoyed killing so much that they didn’t stop their murders even after they switched sides and became FBI informants. They came up with novel ways of killing their victims. Some of the most chilling stories of the Mafia’s deadliest contract killers are given below:

 

 

1. Roy DeMeo

 

Mafia Hitman Roy DeMeo. Photo: The Famous People / Public Domain


Roy DeMeo was born in a working-class Italian family on September 7, 1940. Barely out of high school, DeMeo became a ‘loan shark’, a person who would offer loans to others at high rates of interest but on illegal conditions. DeMeo had worked as an aide to a butcher earlier on. This was later used by the Mafia to its advantage and became DeMeo’s calling card. He developed a method of the dismemberment of his victims that the Mafia needed. 

 

DeMeo initially worked as a loan shark for the Lucchese crime family, one of the 5 crime families of New York. But he was poached by another prominent crime family, the Gambino. Anthony Gaggi, a member of the Gambino family in 1966 promised DeMeo more money if he worked for Gaggi and his boss, Paul Castellano. DeMeo agreed to this and formed his gang and extended his area of operations into the theft of cars and drug trafficking.

 

DeMeo’s first murder occurred in 1973. DeMeo and Gaggi were in the process of extorting pornography magnate Paul Rothenberg. It was Gaggi who ordered DeMeo to kill Rothenberg. Rothenberg had recently been interrogated by the authorities about some suspicious payments which he had made. DeMeo killed Rothenberg after leading him down an alley in the suburb of  Long Island and shooting him in the head.

 

DeMeo used his experience as a butcher to hide traces of those he killed. He named his method after the Gemini Lounge, which was a bar that he owned. The method was very precise and included the victims being taken to the back room of the club and shot in the head with a gun attached with a silencer. Next, the ‘Gemini Method’ called for one member of DeMeo’s gang to quickly coil a towel around the wound and another member stabbed the victim in the heart to stop the flow of blood. The body was then dragged to a bathtub where DeMeo carved, sawed, and cut it up before packing it into boxes and dropping the boxes at a local garbage dump.   

 

DeMeo was allegedly involved in at least 200 murders with his ‘Gemini Method’ during the 1970s. His career came to a bloody end in 1983 when the noose had tightened around the Gambino family. Castellano now considered DeMeo as a liability and ordered Gaggi to get rid of him. DeMeo was found dead and stuffed into the boot of his own car on January 10, 1983. He had been shot many times.

 

 

2. Richard Kuklinski

 

Richard Kuklinski’s mugshot, 1982. Photo: Wikimedia Commons/ Public Domain


Richard Kuklinski, a towering figure six feet five inches tall and weighing 100 pounds, worked for three crime families in New York, the Genovese, DeCavalcante, and Gambino. His cold-blooded methods of murdering his victims and freezing their bodies to deny investigators clues to their deaths resulted in him being given the moniker of ‘The Iceman’.

 

Kuklinski was born on April 11, 1935, in Jersey City, New Jersey to parents of Polish and Irish descent. His father was afflicted with alcoholism and showed violent behavior. He beat Kuklinski and his brother so badly that Kuklinski’s brother ultimately died. Kuklinski shortly after this committed his first murder. He beat to death a local bully before removing identifications from his body. He had a fierce temper which had probably resulted from the abuse which he had suffered at the hands of both his parents. Although his mother was a staunch Catholic, Kuklinski ultimately rejected Catholicism.

 

The Mafia came to know of his killing abilities and Roy DeMeo of the Gambino crime family hired Kuklinski for harassing debtors. He was the main hitman of the Genovese family and a hitman who targeted victims selectively for the DeCavalcante.

 

Kuklinski’s method of killings involved the removal of the teeth and fingers of his victims to stop the authorities from identifying the bodies. His nickname came about because he would many times freeze the bodies to prevent the authorities from knowing the time of death of the victims. As for many others, they were simply thrown into water bodies or in mines.

 

Kuklinski used a variety of weapons including guns, ice picks, grenades, crossbows, and chainsaws to kill his victims. His favorite mode was a nasal spray bottle which was filled with cyanide. By his own admission, Kuklinski murdered between 100 and 200 people. These included another prominent mobster named Jimmy Hoffa.

 

Amazingly, Kuklinski never allowed his children to know about his dark side. All of his three children were educated in good schools and used to vacation in  Disneyland. Kuklinski also served regularly as an usher in his local church and organized barbecue parties in his neighborhood. He also never killed women and children. His family didn’t know of the other side of his personality or his profession before he was caught. However, he was finally trapped by the authorities in 1986.

Kuklinski was convicted of six first-degree murders and sentenced to consecutive life sentences. He died while in prison in 2006 because of Kawasaki disease after suffering inflammation of the blood vessels which couldn’t be cured.

 

 

 

3. Abe Reles

 

NYPD mugshots of Abe Reles. Photo: Burton Turkus Papers, Special Collections, Lloyd Sealy Library, John Jay College of Criminal Justice/CUNY / New York Daily News / Public Domain

 

Abe Reles was one of the foremost and among the first hitmen of Murder, Inc., the organized crime group which was active in the Manhattan suburb of New York City between 1929 and 1941. It had been formed by Bugsy Siegel and Meyer Lansky and hired out hitmen to customers with a guarantee that the contract killings of their victims would be untraceable.

 

Abe Reles was born in the Brooklyn suburb of New York in a Jewish family on May 10, 1906. He was a school dropout and began stealing from local billiard halls and stores selling candy. He was first arrested when he was fifteen years old for thieving gum. Reles was sentenced to four months in prison, following which he ventured into crime full time. He began working for the Shapiro brothers, who ran a gang in Brooklyn. When he was arrested and not helped by the brothers while in custody, he became inimical to them. The brothers also beat and raped his girlfriend, angering him further and he vowed revenge. Around this time, he was hired by Meyer Lansky at Murder, Inc.

 

Reles’ weapon of choice was an icepick which he stabbed into the brains of his victims through their right ear. He once killed a parking lot attendant wantonly for returning his vehicle to him too slowly. With help from Lansky, he took revenge on the Shapiros. He dragged Irving Shapiro out of his house, beat him up, and shot him dead in the street. Irving’s brother Meyer was shot dead in his face at point-blank range. Some years later, the third brother, William was buried alive. Reles was nabbed for the murders in 1940 and soon found involved in many other murders.

 

To avoid getting the death penalty, he turned against Murder, Inc. and gave extensive testimony which ran into thousands of pages. His information resulted in many bodies being dug up and the implication of Harry Strauss, Martin Goldstein, Frank Abbandando, and the co-founders of Murder, Inc. Louis Buchalter and Albert Anastasia. Reles was guarded by 18 New York Police Department (NYPD) officers who stood outside his hotel Half-Moon on Coney Island in 24-hour shifts. 

 

However, on November 12, 1941, Reles’ dead body was discovered on the sidewalk near his hotel, six floors below his room. Ropes in Reles’ hotel room indicated that he had died while trying to escape having fallen from his window. However, many believed that he was killed by the mob or that his killing had been contracted by them to the police because of having turned against Murder, Inc.

 

 

4. Sammy Gravano

 

NYPD Mugshots of Sammy ‘the Bull’ Gravano. Photo: Handout by NYPD / Toronto Sun / Public Domain


Salvatore ‘Sammy’ Gravano was not only one of the most notorious hitmen but also one of the most prominent deserters in the history of organized crime. Before he became an approver and a witness against Gambino crime family boss John Gotti, he killed at least 19 people and was given the moniker of ‘Sammy the Bull’.

Gravano was born on March 12, 1945, in Brooklyn, New York City. He came to the attention of the Mafia when he was 10 years old. He was acknowledged by local criminals while fighting two bullies who had stolen his bike. They noted that he fought like a ‘little bull’. He dropped out of high school and served in the Vietnam War for one tour. 

Gravano was hired by the Colombo crime family and was initially ordered to carry out thefts. He started murdering in 1970 when he was asked by his bosses to kill a colleague, who had become unfaithful to them. But Gravano’s rapid rise through the ranks began to cause friction in the family and he switched sides to the Gambino family in 1976. This led to very bad results. 

Gambino murdered his own brother-in-law in 1978 when he discovered that he had a major drug problem. The only part of his body which the police discovered was one of his hands. In the meantime, Gravano continued to make millions in the corrupt construction business as a loan shark and opened his own club in Bensonhurst in Brooklyn.

Matters came to a head in 1982 when Garvano’s Boss, Paul Castellano, sold the venue of Gravano’s club to a local drug dealer named Frank Fiala. Gravano was so angry that he had his gang shoot Fiala in the head and urinated into his corpse’s mouth. It led to Gravano becoming inimical to Castellano. Gravano tied up with the rising mob boss John Gotti to kill Castellano. This took place on December 16, 1985, at the Sparks Steak House in the Manhattan suburb. Gravano started working for Gotti following this as his hitman. They were both arrested on charges of racketeering in 1990. 

Gravano came to know that Gotti was planning to pin the blame for the murders on him, Gravano testified against Gotti in court and claimed that 10 of the 19 murders committed by him had been ordered by Gotti. This resulted in Gotti being given a life sentence while Gravan got a lessened sentence of five years. 

On being told that his boss was plotting to pin the blame of all of his murders on Gravano, he (Gravano) agreed to testify against Gotti and revealed that 10 of the 19 murders he had committed were ordered by Gotti. This led Gotti to be imprisoned for life. Meanwhile, Gravano received a reduced sentence of five years.

 

 

5. Harry Strauss

 

Harry “Pittsburgh Phil” Strauss. Photo: Eleventh stack / WordPress / Public Domain


Harry Strauss was an established hitman of Murder, Inc. and like Abe Reles, he led the murderous operations of Murder, Inc. He was born in Brooklyn, New York on July 28, 1909, and had been detained 17 times by the time he was in his mid-20s. He didn’t live up to thirty years of age.

Strauss earned the moniker of ‘Pittsburgh Phil’, Strauss is believed to have killed up to 500 people. He was one of the most reliable hitmen in the criminal world and was sent regularly on contract killings across the country. His weapon of choice was an icepick but he is reported to have used an axe to kill a man in a cinema hall.

The most disturbing fact was the amount of pride that Strauss took in his work. He always dressed up in nice clothes and many times took up jobs only for the pleasure of killing. Wherever he had gone for the killing, he would often stay there for an extra day just to see how the local press covered his exploits. His victims were mainly informers or hitmen who had fallen foul of Murder, Inc.  

Strauss was much in demand when he arrived from outside the town where he would be a mystery to the local police. It was tough for the authorities to pin the blame of killings on him including the 1937 murder of the Purple Gang hitman Harry Millman whom Strauss murdered in an eatery in Detroit with his gun. He also wounded 5 others.

Whereas the New York assistant district attorney Burton Turkus was irritated that Strauss had not even been convicted of a small-time crime, the situation changed when Strauss’s former colleague Abe Reles gave testimony against Murder, Inc. in 1940. With Reles implicating Strauss as a murderer, he was made to stand on trial.

Despite Strauss attempting to falsely show that he was insane during the trial, he was convicted in the murder of Irving Feinstein due to the evidence against him and he was sentenced to death by electric chair. He spent the last months of his life in Sing Sing Prison and didn’t stop faking his insanity until his execution in June 1941.

 

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