10 Deadliest Mob Hitmen of All Time

In the world of organised crime, the hitman was the final word. No appeal. No second chance. The men on this list were the most lethal contract killers in American Mafia history — professionals in the truest and most chilling sense of the word.

1. Harry “Pittsburgh Phil” Strauss — 100+ Murders

Harry Strauss — known as Pittsburgh Phil or simply Pep — was the most prolific contract killer in the history of American organised crime. A member of Murder Incorporated, Brooklyn’s contract killing arm, Strauss is believed to have personally carried out over 100 murders during the 1930s — travelling across the country to carry out assignments in multiple states, which made him extraordinarily difficult to prosecute.

His weapon of choice was the ice pick. He was reportedly capable of driving one through a victim’s ear canal so precisely that the resulting wound was indistinguishable from a natural brain haemorrhage. He approached killing with something closer to enthusiasm than professional neutrality — joking about hits over dinner, treating each assignment as a sport.

When fellow Murder Inc member Abe Reles turned government witness in 1940, Strauss was convicted of murder. He attempted to turn witness himself — that failed. He then feigned insanity — the court didn’t believe him. He was executed in the electric chair at Sing Sing Prison on 12 June 1941, aged 33.

2. Richard “The Iceman” Kuklinski — 200+ Claimed

Richard Kuklinski was a contract killer from New Jersey who worked for the DeCavalcante and Gambino crime families. In a series of extraordinary prison interviews broadcast on HBO in the 1980s and 1990s, Kuklinski claimed to have killed over 200 people across three decades using an astonishing variety of methods — firearms, knives, crossbows, cyanide and on at least one occasion, a bomb.

He earned the nickname the Iceman because he stored some victims’ bodies in a chest freezer for months before disposing of them — a calculated method to disguise the time of death and confuse investigators trying to establish alibis.

Kuklinski was remarkably compartmentalised. For most of his killing career, his wife and children had no idea what he did for a living. He was convicted in 1988 after an undercover ATF operation and sentenced to life. He died in prison in 2006, aged 70. Whether all his claimed kills were genuine remains disputed — but law enforcement confirmed enough of them to make him one of the most dangerous men ever to work for the mob.

3. Harry “The Hook” Aleman — 13+ Confirmed

Harry Aleman was the Chicago Outfit’s most reliable and feared hitman during the 1970s. He earned the nickname The Hook from his boxing background as a teenager — a left hook that served him well in his later profession. He was credited with at least 13 confirmed murders, was comfortable shooting in public, and frequently used silenced weapons.

What made Aleman remarkable was his near-immunity from prosecution. In 1977 he was tried for the murder of William Logan — and acquitted. Decades later it emerged that the trial judge, Frank Wilson, had been bribed $10,000 to deliver the acquittal. This extraordinary revelation allowed prosecutors to retry Aleman on double jeopardy grounds — ruling that since the original trial was corrupt, it had never been a valid proceeding. He was convicted in 1997 and died of cancer in prison in 2011.

4. Joseph Meldish — ~40 Murders

Joseph Meldish began his criminal career at 18 in the Bronx, quickly becoming a contract killer for the Genovese and Lucchese crime families. He operated for nearly two decades with minimal law enforcement interference — a testament to both his professionalism and the difficulty prosecutors faced in connecting him to specific crimes.

He is believed to have been involved in approximately 40 murders. He was finally convicted in 2011. His brother Michael, also a mob associate, was shot in 2013 — a reminder that in the mob world, the violence rarely stays contained to those who choose it.

5. Jorge Ayala — 35+ Murders

Jorge Ayala was the primary enforcer for Griselda Blanco — the Godmother of Cocaine — during Miami’s brutal cocaine wars of the late 1970s and early 1980s. He was responsible for at least 35 drug-related murders, carrying out hits with ruthless efficiency as Blanco consolidated control over Miami’s cocaine trade.

Ayala eventually pled guilty to three murders and became a government witness. His testimony was later compromised in extraordinary fashion — it emerged that he had been conducting phone sex conversations with secretaries from the state attorney’s office while in custody. The scandal damaged his credibility as a witness significantly, adding a darkly comic footnote to one of Miami’s most violent criminal careers.

6. Harry “Happy” Maione — 12+ Murders

Harry Maione served as the Italian liaison within the largely Italian-Jewish Murder Incorporated operation — a crucial role in keeping the organisation’s two ethnic factions working in alignment. He personally carried out at least 12 murders between 1931 and his arrest, operating from the Brownsville neighbourhood of Brooklyn where Murder Inc was headquartered.

Maione was convicted on the testimony of Abe Reles and executed in the electric chair at Sing Sing Prison on 12 June 1941 — the same day as his Murder Inc colleague Frank “Dasher” Abbandando and Pittsburgh Phil Strauss. Three of the organisation’s most lethal members were executed on the same day.

7. Wayne “Silk” Perry

By the late 1980s, crack cocaine had devastated Washington DC, and Alberto “Alpo” Martinez had built one of the city’s most profitable drug operations on its back. To protect it, he hired Wayne Perry — a man with no hesitation whatsoever about killing. Perry and his crew carried out executions for the Martinez organisation for years, making him one of the most feared figures in DC’s criminal underworld.

In 1992, police investigations combined with Alpo’s own cooperation charged Perry with at least five murders. He was sentenced to life in prison. His story became part of the fabric of DC street lore — a reputation for violence so complete that even other criminals gave him a wide berth.

8. Chester Wheeler Campbell

Chester Wheeler Campbell worked across Detroit’s criminal landscape throughout the 1970s and 1980s — serving both the Italian Mafia and the city’s urban drug lords with equal facility. What distinguished Campbell from most hitmen was his extraordinary intelligence operation. He had more surveillance equipment than most police departments of the time, and his personal notebooks documented approximately ten unexplained murders alongside the detailed movements of virtually every significant criminal, cop, prosecutor and judge in Detroit.

A master of delegation, Campbell made others do most of the physical work while he orchestrated from a distance. Even after imprisonment he continued tormenting law enforcement with years of legal motions and lawsuits — a final demonstration of the control he maintained over his environment.

9. Irving “Big Gangi” Cohen

Irving Cohen’s most notorious assignment came in 1937 when Murder Inc bosses needed to eliminate Walter Sage — and chose Cohen to do it precisely because Sage trusted him. Cohen fulfilled the contract by driving an ice pick into Sage’s skull, then fled the scene and went into hiding in Los Angeles.

His concealment proved short-lived. Los Angeles police apprehended him after he turned up on a film set — apparently convinced that a new career in the movie industry would provide adequate cover. He was extradited back to New York to face justice. The incident captures something essential about Murder Inc’s world — even the killers couldn’t always outrun what they’d done.

10. Bugsy Siegel — Founding Member of Murder Inc

History remembers Bugsy Siegel as the visionary who built the Flamingo Hotel and transformed Las Vegas. What is less widely remembered is that before the suits and the casinos, Siegel was a prolific killer — one of the most active gunmen in the early American Mafia and a founding member of Murder Incorporated alongside his childhood friend Meyer Lansky.

Siegel personally participated in the murders of Joe Masseria and Salvatore Maranzano in 1931 — the two hits that ended the Castellammarese War and allowed Lucky Luciano to reorganise American organised crime entirely. He was capable of extraordinary violence and had a hair-trigger temper that earned him his nickname — a period slang term for someone erratic or crazy, which he deeply resented.

Siegel was himself killed in Beverly Hills on 20 June 1947, shot through the living room window of Virginia Hill’s home. The murder was never officially solved — a fitting end for a man who had spent his life in the shadows of organised crime. See the Bugsy Siegel death photos →

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