9 Real-Life Hitmen And Their Assassinations

There’s something endlessly fascinating about hitmen in fiction. Assassins are likely the coolest and most exciting parts of James Bond movies, gangster stories and conspiracy thrillers. The idea that someone is so efficient at killing high-profile targets that they can make a living from it is a compelling idea, and not one we expect to be based in any fact.

Just as the lives of spies tend to involve a lot more paperwork and uneventful meetings than Hollywood would like us to believe, a lot of conspiracies and assassination attempts tend to be revealed as one-off attacks, motivated by political beliefs or simply the actions of an unstable loner. Yet this isn’t necessarily the case. In fact, there have been many genuine contract killers in the world, some with dozens of deaths to their name.

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.

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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.

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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.

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