If things get so desperate for you that you contemplate killing someone to collect on insurance, be sure you find a cooperative victim. That lesson was learned the hard way by the men who tried to kill Michael Malloy.

Tony Marino, Joseph “Red” Murphy, Francis Pasqua, Hershey Green, and Daniel Kriesberg came up with a get-rich-quick scheme in January 1933. They took out three insurance policies on Michael Malloy, a New York City homeless man. The policies were worth $3,500 ($64,504.73 in 2017 value). They assumed no one would look too closely at the death of a homeless man, particularly if he died under the right circumstances.

The first attempt at killing Malloy involved letting him drink himself to death. Marino owned a speakeasy and offered Malloy unlimited credit, thinking the man would soon succumb to alcohol poisoning. Malloy appeared to be cooperating, drinking non-stop for most of the day, but by the next day, he was back, ready for more.

At this point, the conspirators decided to speed things along a bit. They replaced the alcohol with antifreeze. Malloy passed out, and the men thought they had succeeded. They were wrong. Malloy woke up and asked for more of the same. This time they gave him turpentine — and then horse liniment — and then rat poison. Malloy just kept swallowing the stuff and asking for more.

Deciding the drink wasn’t going to do the trick, they offered Malloy raw oysters, soaked in wood alcohol. When that didn’t work, they tried something with a bit more of a bite: rotten sardines mixed with carpet tacks. Guess what? Malloy was unfazed.

Deciding that Malloy’s stomach must be impervious to attack, the conspirators regrouped and tried a different tactic. On a night when the temperature reached −14° F (−26° C), they gave Malloy drink after drink (unpoisoned) until he passed out. They drove him to a park, stripped off his shirt, dumped him in a snow bank, and poured five gallons (19 liters) of water on his chest. They returned home, thinking this would surely be the end of Malloy. The next day they were astonished to find Malloy back at the speakeasy, ready for another round of drinks. He complained of a “wee chill.”

Now getting really desperate, the gang went for a sure-fire approach. They waited until Malloy stumbled out of the speakeasy one night and ran over him with Green’s taxi. The car hit Malloy at 45 mph (72 kph). This did not succeed in sending Malloy to the morgue, but it did send him to the hospital for three weeks. The would-be assassins were sure they had killed Malloy. When he was discharged from the hospital, the first place he visited was the speakeasy. His greeting: “I sure am dying for a drink!”

That set them off. After more than a month of trying to kill Malloy and make it look like an accident, the time for subtlety had passed. On February 22, 1933, the conspirators again got Malloy so drunk that he passed out. They carried the unconscious man to Murphy’s residence, where they connected rubber tube from a gas light fixture to Malloy’s mouth. They wrapped a towel was wrapped tightly around his face and turned on the gas. This, finally, accomplished the task. Malloy was dead an hour later.

A check for $800 from the Metropolitan Life Insurance Company, the only money the gang of murderers collected.

With the help of Pasqua’s friend, Dr. Frank Manzella, the death certificate showed the cause of death to be “lobar pneumonia.” This allowed them to cash in the Metropolitan Life Insurance policy for $800. As it turned out, that was the only money the murders would get.

When they attempted to cash in on the next policy, it triggered an investigation. Police exhumed Malloy’s body, and it wasn’t long before the five conspirators were charged with first-degree murder. Newspapers dubbed the gang “The Murder Trust,” and the trials became the talk of the town.

All five were convicted of first-degree murder. Hershey Green was sentenced to life imprisonment. The other four men were ordered to die by electric chair. The sentences were carried out at Sing Sing Prison. Kriesberg, Marino and Pasqua were executed on June 7, 1934, and Murphy was put to death on July 5, 1934.

Incidentally, all four men were killed on the first attempt.

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