Michael Malloy - Tougher than your mum.
Marino owned a speakeasy and gave Malloy unlimited credit, thinking Malloy would abuse it and drink himself to death. Although Malloy drank for a majority of his waking day, it did not kill him. To remedy this, antifreeze was substituted for liquor, but still, Malloy would drink until he passed out, wake up, and come back for more. Antifreeze was substituted with turpentine, followed by horse liniment, and finally mixed in rat poison. Still, Malloy lived.
The group then tried raw oysters soaked in wood alcohol. This idea apparently came from Pasqua, who saw a man die after eating oysters with whiskey.Then came a sandwich of spoiled sardines mixed with poison and carpet tacks.
When that failed, they decided that it was unlikely that anything Malloy ingested was going to kill him, so the Murder Trust decided to freeze him to death. On a night when the temperature reached −14 °F (−26 °C), Malloy drank until he passed out, was carried to a park, dumped in the snow, and had five gallons (19 L) of water poured on his bare chest. Nevertheless, Malloy reappeared the following day for his drink. The next attempt on his life came when they hit him with Green's taxi, moving at 45 miles per hour (72 km/h). This put Malloy in the hospital for three weeks with broken bones. The gang presumed he was dead but was unable to collect the policy on him. When he again appeared at the bar, they decided on one last approach.
On February 22, after he passed out for the night, they took him to Murphy's room, put a hose in his mouth that was connected to the gas jet, and turned it on. This finally killed Malloy, death occurring within an hour.
https://en.wikipedia.org/wiki/Michael_Malloy