Compared to the various other methods of murder, contract killing is strictly business. When an organization requires the disposal of an undesirable person for one reason or another, they often hire professionals who can kill quickly, discreetly, and leave little trace. There are, however, some hitmen who excelled in their chosen profession, with some being remembered as the most successful hitmen in history.
Make no mistake, however, as not all contract killers and hitmen work for criminal organizations. While many of the killers on this list plied their trade for organized crime syndicates like the Cosa Nostra and the Russian mob, there’s one killer who worked with a license to kill from his country’s government. No matter how you slice it, contract killing is a dirty business made for a particular type of person. In this article, we will explore 10 of the most successful hitmen in history. Some of them are prolific, some are notorious, but all of them are cold-blooded killers.
To compile a list of the most successful hitmen in history, 24/7 Tempo consulted a range of crime and lifestyle publications including All That’s Interesting and The New York Times. Next, we selected hitmen from a range of eras and organizations who, through prolificity or fame, made a noticeable cultural impact. After that, we confirmed biographical information using sites like Britannica. (For specifically female criminals, discover 30 of the most brutal female criminals in world history.)
Richard Kuklinski
One of the most successful hitmen in history is Richard Kuklinski. Born into an extremely abusive family, Kuklinski took to crime at an early age. From there, he became involved in various criminal activities for most of his life. His entry into contract killing, however, came while he worked at a Manhattan film lab, bootlegging various movies and distributing pornography. There, he killed his first victim, George Malliband who sought to buy some of Kuklinski’s bootleg movies.
From there, Kuklinski became a feared, if not shadowy, contract killer in New Jersey. Though never a member of the mafia, he nevertheless appeared to do various contract killings for different families in the decades that followed. After police linked his burglary gang with numerous unsolved murders, Kuklinski was charged with five murders along with various other charges.
While in prison, Kuklinski famously granted interviews to various law enforcement specialists like criminal profilers and behavioral psychologists. During these interviews, Kuklinski claimed to have killed over 100 people throughout his career. While these numbers have since been disputed, Kuklinski no doubt, was successful in crafting an image of the cold, collected hitman for the public.
Julio Santana
Another one of the most successful hitmen in history is Julio Santana. Raised in the jungles of Brazil as a devout Christian, he expected to become a farmer or fisherman upon maturity. That all changed, however, when his professional hitman uncle asked him to kill a local fisherman and alleged rapist.
Though he vowed never to kill anyone after his first contract killing, Santana nevertheless continued in his burgeoning career with great success. His work attracted the notice of the Brazilian government, which hired Santana between the years of 1967 and 1974 to assist in fighting communist insurgents in the Araguaia River basin. During this time, he also killed various politicians, guerilla leaders, and even schoolteachers.
He gave up the hitman life after his wife gave him an ultimatum in 2006. Nevertheless, Santana has arguably the highest body count of any hitman in history. As per his meticulously documented notebook, he’s believed to have killed nearly 500 people during his career as a contract killer.
Alexander Solonik
Another one of the most successful hitmen in history is Alexander Solonik. Born in the Kurgan region of the Soviet Union, he was childhood friends with neighbor Andrei Kolegov, who would later lead the Kurgan Criminal Organization. Upon finishing school, Solonik was drafted into the military. After his service, he became a police patrolman. During this time, however, he was convicted of rape charges and sent to prison.
Upon release, Solonik found himself in his childhood home of Kurgan. He quickly joined the local criminal gang and became a hitman. In the years that followed, Solonik gained a reputation for his contract killing, claiming credit for the executions of various Russian mob figures and leaders. Naturally, this attracted the attention of law enforcement, who cornered him in a Moscow Marketplace. Though he killed two officers in the ensuing struggle, Solonik was rearrested and sent back to prison.
Thanks to an alleged mob sleeper agent, however, Solonik escaped confinement in 1995 and disappeared from Russia. He surfaced again in Greece, having set up a new criminal organization that specialized in drug dealing and contract killings. Soloniks luck would run out, however, as his body was found near Athens only two years later.
Giuseppe Greco
Another one of the most successful hitmen in history is Giuseppe Greco. Born in the city of Ciaculli in Sicily, Greco started in the mafia as a driver for a higher-ranking mafioso. By 1979, however, Greco consolidated his power and influence to such a degree that he was granted a seat on the Sicilian Mafia Commission.
During the Second Mafia War between 1981 and 1984, Greco’s skill for killing truly flourished. Preferring collaboration, Greco led a team of contract killers that carried out countless murders in Sicily. With Greco at the helm, the group killed rivals, witnesses, policemen, and mafia leaders. Greco also reportedly worked at the “Rooms of Death,” a small apartment near Piazza Sant Erasmo where scores of people were tortured and killed.
Though he was the underboss of the Ciaculli family by this time, Greco preferred to take care of contract killings himself. By the mid-1980s, Greco became too powerful. This led his longtime collaborator Salvatore Riina to order his execution. Greco was killed in his home by his friends in September 1985. Later, an Italian court convicted Greco in absentia of 58 murders, making him one of the most prolific hitmen in history.
Thomas Pitera
Another one of the most successful hitmen in history is Thomas Pitera. Growing up in Brooklyn, New York, Pitera was bullied by classmates for his high-pitched voice. Later, Pitera became fascinated with martial arts, joining a dojo in Brooklyn and rising to the top of his class. After winning a Kumite karate competition, Pitera moved to Japan where he spent 27 months studying under martial arts master Hiroshi Masumi. After his scholarship ended, Pitera worked at a chopstick factory to fund his continued stay in Japan.
This would not take, however, as Pitera returned to Brooklyn, joined the Bonanno Crime Family, and soon became one of their most feared soldiers. His time studying martial arts led to his mafia nickname of “Tommy Karate”. As he steadily rose through the ranks and became a made man, Pitera carried out numerous contract killings. Taking an almost artistic approach to his killings, Pitera studied books on dissection and carried around a special kit for cutting up bodies. According to him, he preferred to dispose of his victims in the Staten Island Graveyard. There, he believed the damp soil and wildlife would accelerate the decomposition of bodies.
Nevertheless, in 1990 Pitera and his crew were indicted for drug dealing and murder. After crewmember Frank Gangi testified to his ruthless series of murders, the court convicted Pitera of six murders. Though he ultimately avoided the death penalty, investigators believe Pitera committed up to 60 murders during his time in the mafia. (For other shockingly brutal killers, discover 20 of the all-time most heinous criminals.)
Charles Harrelson
Another one of the most successful hitmen in history is Charles Harrelson. Born in Lovelady, Texas, Harrelson worked as an encyclopedia salesman and professional gambler before serving prison time for armed robbery. It was during this time that Harrelson began committing contract killings for various underworld figures.
In 1968 he was tried but ultimately acquitted for the murder of Alan Harry Berg. Soon after, he was tried for the contract murder of grain salesman Sam Degelia Jr. Though the trial ended in a deadlocked jury, a few years later Harrelson was retried and convicted for the murder. After serving five years, he was released for good behavior. Less than a year later, however, Harrelson was implicated in the killing of U.S. District Judge John H. Wood Jr.
Finally, the charges stuck, and Harrelson was sentenced to two life terms for the judge’s murder. Though rumors abound regarding his possible involvement in the assassination of President John F. Kennedy, it remains inconclusive. Harrelson, surprisingly, is also the father of famed actor Woody Harrelson.
Roy DeMeo
Another one of the most successful hitmen in history, and one of the most brutal, is Roy DeMeo. Born and Raised in Flatlands, Brooklyn, DeMeo first entered the criminal world as a loanshark during high school. After his father died and his mother and brother moved back to Italy, DeMeo found a surrogate family in the Lucchese Crime Family.
A successful criminal, DeMeo rose through the ranks thanks to his various loansharking, chop-shop, and bank fraud schemes. This, no doubt, also attracted enemies to be disposed of, and DeMeo slowly put together a crew to help him accomplish this. They named their assembly line style execution method the Gemini Method after the lounge where they conducted their business.
There, DeMeo and various members of his crew would lure in victims, and shoot them with a silenced pistol while immediately covering the wound with a towel. Then, a crew member would stab the victim in the heart to stop all blood flow. Next, the body would be dragged into the bathroom, hung up, and drained of blood. From there, the body would be placed on plastic sheets, dismembered, and disposed of at the Fountain Avenue Dump in Brooklyn.
This method proved so effective, that DeMeo remained in the criminal business for another decade. During this time, he expanded his auto theft business into the largest in New York State. By 1982, however, not only did the FBI link scores of murders to DeMeo, his criminal collaborators had grown tired of his dealings. Less than a year later, his body was found in the trunk of his car. During his extensive criminal career, DeMeo and his crew are believed to have killed up to 200 people using their Gemini Method.
Joseph Barboza
Another one of the most successful hitmen in history is Joseph Barboza. Born into a Portuguese emigrant family in New Bedford, Massachusetts, Barboza would have a successful first career as a boxer. Known for his powerful swing, Barboza won eight out of the eleven professional matches in which he boxed. Though he later worked as a longshoreman, he soon gained employment in the powerful Patriarca Crime Family.
His true entry into the underworld would begin after he was imprisoned at the Concord Prison in Massachusetts. There, he led the largest prison break in the facility’s history. Though he was later rearrested, Barboza was introduced to various organized crime figures. Upon release, he established a criminal crew under the eye of crime boss Stephen Flemmi. While he was never officially inducted into the family, he quickly gained a reputation for being one of New England’s deadliest contract killers.
His time near the mob was too turbulent for his liking, however. In 1967, while imprisoned for a murder, Barboza turned FBI informant. This led to his role as a witness in trials against various mob figures over the next few years. Upon release, the government gave him a fake name and an apartment across the country in San Francisco. His collaborators turned rivals, however, quickly found out where he was staying and killed him on February 11, 1976. He is alleged to have committed at least 26 contract killings during his career.
Giovanni Brusca
In many ways, famed hitman Giovanni Brusca was destined for his life of crime. Born into a mafia family, he was connected from birth. This helped him be named head of the San Giuseppe Jato district of Palermo, Sicily in 1985. After that, Brusca embarked on an extremely violent career, even by Sicilian mafia standards.
During his time as mafia leader, Brusca ordered countless executions and personally took part in just as many. Some of his notable killings include that of anti-mafia prosecutor Giovanni Falcone, businessman Ignazio Salvo, and the 11-year-old son of a collaborator turned government informant. In the early 1990s, Brusca again made the news for his involvement in various bombings on the Italian mainland which left 10 people dead and dozens more injured.
His crimes finally caught up with him, however, and Brusca was arrested and convicted for various deeds in 1997. While incarcerated, Brusca also turned government informant. Due to good behavior and the information he provided, Brusca was miraculously freed in May 2021. Brusca is believed to have committed a stunning 100 to 200 murders during his time in the mafia.
Abe Reles
The son of Jewish immigrants, hitman Abe Reles was born and raised in the Brownsville section of Brooklyn, New York. After dropping out of school in eighth grade, he earned a different kind of education hanging around local pool halls and candy stores. After stealing some candy, Reles was sent to a juvenile detention center for four months.
From there, Reles would be in and out of jail, eventually entering the slot machine business with childhood friends and future mafiosos Martin “Buggsy” Goldstein and Harry “Pittsburgh Phil” Strauss. Eventually, this group of friends would become Murder, Inc. one of the most feared and violent criminal organizations in American history. Reles, in particular, gained a reputation for being a crazed and unscrupulous killer. Besides the countless contract killings Reles committed, he was known for his indiscriminate killings of non-affiliated people in broad daylight.
After he soured on his criminal associates and was implicated in multiple murders, Reles became a government witness. With his information, numerous Murder Inc. associates were tried and convicted. When he was set to give information about high-ranking Cosa Nostra member Albert Anastasia, however, he met death. Though he was under the watch of numerous police officers, Reles somehow fell out of a fifth-floor window to his death. While it was initially deemed an accident, numerous pieces of evidence point to the Mafia’s involvement in the incident. (For other infamous ne’er-do-wells, discover the most notorious criminal in every state.)