1. Dr. Glennon Engleman
Glennon Engleman was a St. Louis dentist who moonlighted as a hitman for nearly 30 years. He has seven confirmed murders between 1954 and 1980, once stating that his talent was to kill without remorse. He killed his victims in various ways, usually for financial reward. First, he killed his ex-wife’s new husband by shooting him with a sniper rifle, and then took out a colleague to whom he owed $14,000 by blowing up her car.
The most bizarre incident came when he killed a business associate by hitting him with a rock, pushing him down a well before blowing him up with dynamite, sharing the insurance payout with the widow. In prison, he confessed to being hired by a woman to kill her parents-in-law and husband so she could inherit the family’s oil business. He shot the father and beat the mother to death, before taking out the son 17 months later.
2. Mr Rent-a-Kill
Christopher Dale Flannery, who had the moniker of “Mr. Rent-A-Kill”, was an Australian contract killer. He was primarily under the employ of crime boss Neddy Smith during the Sydney gang wars of the early 1980s. One of his first jobs was to kill a barrister; running him off the road, abducting him, before shooting him in the head. It’s believed his personal bodycount is at least a dozen people.
In and out of jail without enough evidence to be convicted, Flannery supposedly became increasingly unstable, to the point where even his boss was unable to control him. The police tried to negotiate an end to the violence, to which Flannery replied: “You’re not a protected species, you know – you’re not a f***ing koala!” He disappeared in 1985, and is presumed dead by the hands of his boss, the police, or one of the many enemies he made over the years.
3. Bugsy Siegel
Benjamin “Bugsy” Siegel was a mobster who operated in New York, then later Los Angeles and Las Vegas. He began as a bootlegger during the Prohibition Era, gaining significant influence in the mafia. He was one of the founders and leaders of Murder Inc. – an organisation of various mafia groups in the U.S. at the time, responsible for up to 1,400 killings.
His primary role was to carry out hits himself, as well as arrange for others to do so. No one knows exactly how many people Bugsy himself killed, but his personal body count could very well have been in the hundreds. Bugsy was eventually killed by another hitman in 1947, supposedly over his gambling debts.
4. Alexander Solonik
Also known as “Sasha the Macedonian” and “Superkiller”, this Russian contract killer specialised in killing mob bosses. After leaving the army, he joined the OMON police force, but was expelled during training for being too violent. He became involved with the mob and killed at least 30 people, including an infamous hit where he shot a man in a crowded nightclub, despite the fact he was surrounded by bodyguards. His trademark was dual-wielding pistols, which inspired Agent 47 of the Hitman video game franchise.
He escaped arrest once by jumping from a second story window. During his second arrest, the officer failed to search him properly, and he drew a small automatic weapon from his coat and shot several officers before being apprehended. In prison he was attacked for being ex-police, but reportedly took on as many as 12 inmates at a time. A mob sleeper agent helped him escape, and he fled to Greece, where he set up a kill-for-hire operation. He was found dead in Athens in 1997.
5. Jorge Ayala
Ayala was the favoured hitman for Miami cocaine kingpin Griselda Blanco (also known as “The Godmother”), taking care of all her human disposal needs. Working directly underneath the lead distributor for the Medellin Cartel in Miami in the 70s through to the 80s, he enforced the excessive violence his boss requested. He’s linked to 35 murders during this time, at the height of the Miami Coke Wars, but the real number is expected to be much higher.
6. Pittsburgh Phil
Harry “Pittsburgh Phil” Strauss was the most prolific of hitmen working for Bugsy Siegel’s Murder Inc. He was known for never carrying a weapon in case he was stopped by the police. Instead, he would look for whatever was on hand to use at the scene of the crime. He was known to use guns, bats, ice picks, screwdrivers, bricks and extension chords to get the job done. He’s linked to at least 100 murders during his career, but some historians speculate that he could have killed as many as 500 people.
7. The Iceman
Associated with the mafia in New Jersey and New York City, Richard “The Iceman” Kuklinski was convicted of killing five people, though he likely killed several dozen more. He was given his nickname after his method of freezing his victims to hide the time of death. He would also avoid arrest by always changing the murder weapons, cycling between guns, tire irons, cyanide and knives.
Once arrested, he claims to have murdered between 100 and 250 people in his 30-year criminal career. If we take his word for it, he may be the most prolific contract killer in U.S. history. Three documentaries, two biographies and a film have been made about the killer, based on the interviews with him and the task force that brought him down.
8. Charles Harrelson
The strangest thing about Charles Harrelson, nicknamed “Maximum John”, is that he is the estranged father of actor Woody Harrelson. Apparently, he left his wife to take care of his children alone when Woody was very young. He became a professional gambler, and supplementing his income with the occasional contract kill.
After he left his family, they heard nothing about him until 1981, when Charles was arrested for assassinating U.S. District Court Judge John H. Wood. He was hired by a drug dealer that was on trial with the judge that week, and Wood became the first federal judge to be killed in the 20th century. Harrelson is linked to three killings, though the number may be higher. He has also told several people that he was part of the assassination of John F. Kennedy, though the FBI ruled out his involvement.
9. Giuseppe Greco
Greco was a high-ranking member of the Sicilian mafia, and led death squads to wipe out his clan’s rivals. Even as he rose up through the ranks, he still insisted on taking out targets personally, with his favourite choice of weapon being the AK-47. He was one of the most prolific killers in criminal history, convicted of 58 murders, and suspected of being responsible for 80, while some claim the number is closer to 300.
He worked with the boss of the Corso de Mille neighbourhood in Palermo in the “Room of Death”, a shack where victims were tortured, killed, thrown into vats of acid or dismembered and thrown into the sea. In 1983, he planted and detonated a car bomb that killed a magistrate, and was effectively running the clan while the boss was in hiding. By 1985, his actions were deemed overly-ambitious, and he was killed by his fellow Mafiosi in his home.