Michael Malloy was a fifty-year-old erstwhile fireman and a full time drunk. Like many in his situation, he spent more time drinking than employed, but because he lived in the early 1930s in New York, his hobby happened to be illegal. A regular at the local speakeasy, Malloy also became the central figure in another crime: insurance fraud. The scam: kill someone and collect on his life insurance policies. His role: be the guy who dies.

Michael Malloy was not very good at this.

At the end of 1933, Prohibition, too, would come to a close. But that January, five men at the speakeasy Malloy frequented came up with a get-rich-quick scheme. The plan was simple: Malloy, a homeless alcoholic who appeared on the verge of death anyway, would be tricked into taking out three life insurance policies naming the five schemers as beneficiaries. One of the five, a man named Tony Marino, would provide Malloy with all the liquor he could drink, and then some. Malloy, as the plan went, would drown himself in booze, finally dying.

As recounted by the New York Daily News, the first part of the conspirators’ plan went off without a hitch. Malloy was promised free drinks in exchange for signing a series of petitions which, purportedly, aimed to place a candidate friendly to the speakeasies on the ballot for an upcoming election. In truth, he was signing the forms needed (assisted, we speculate, by a crooked insurance rep) to open up life insurance policies worth over $60,000 in today’s dollars if Malloy were to die accidentally. But from that point on, everything went wrong.

Drinking — hour after hour for days on end — did not kill Malloy. So they upped the ante, replacing his drink with antifreeze. Malloy passed out but survived — and returned to the speakeasy for more free drinks. So the quintet tried turpentine instead of antifreeze. Malloy again survived and returned for more. Turpentine yielded to horse liniment. Same result. And Malloy, finally…

No, he still survived.

In fact, he’d survive a few other attempts at poisoning: rat poison in his “drinks,” oysters soaked in methanol, and sardines mixed with poison and carpet tacks. But none were able to fell Malloy. The would-be murderers turned to a different tactic: wait for a very cold night, get him so drunk that he’d pass out (which he regularly did anyway), and dump him into the snow in sub-zero temperatures. The next day? Malloy returned to the bar for a drink.

With subtle methods failing, the group went with a more direct approach. One of them, Hershey Green, operated a taxi. They got Malloy drunk (again, this was the easy part) and then ran him over while driving at 45 miles per hour. And finally, Malloy went to the hospital. And three weeks later, he returned the bar, battered and injured but very much alive.

In the end — and yes, Malloy’s life finally came to an end — the five guys afterward dubbed the Murder Trust stuck a gas pipe down a passed out Malloy’s throat. On February 22, four to six weeks into the campaign to kill him, Malloy died, officially of pneumonia, and was buried. But the conspirators could not keep their plan from leaking out, as Malloy’s ability to avoid death became the stuff of local legend. Ultimately, officials exhumed Malloy’s body and via an autopsy, detected foul play. The five conspirators were tried for murder and convicted; all except Green were executed for their crime.

Bonus fact : In 2007, New York City began a program which aimed to get homeless people off the street while relieving pressure on the shelters they would have otherwise gone to. The solution: one-way tickets to other cities where the homeless person in question has family members who will take them in.

From the Archives: Liquor, Sicker: Prohibition, poison, and murder — but not from insurance fraudsters.

Related: “On the House: The Bizarre Killing of Michael Malloy” by Simon Read. Four and a half stars on 12 reviews.