The killers wore trench coats and Russian fur hats, and John Gotti, who had planned the hit, along with Sammy "The Bull" Gravano, watched from a nearby car to confirm Castellano's death.
Howard Blum described the event as daring due to its timing and location.
Castellano, aged 70, was the reputed boss of the Gambino crime family in New York City. Gotti, 45, was a member of the family who disagreed with Castellano's order to stop drug trading.
Despite Castellano's concerns about federal attention, Gotti continued to deal drugs, leading to the exposure of wiretaps revealing their activities.
"They figured their days were numbered," Blum says. "So rather than wait around for Castellano to get to them, they planned a very daring hit on the mob boss."
After killing Castellano, Gotti succeeded him as the leader of the Gambino family, and went on to become one of the notorious mob bosses in history.
The federal government took Gotti to trial three times in the late '80s, failing each time to get a conviction.
Gotti's seeming inability to be charged earned him the nickname "Teflon Don."
In 1992, the government finally convicted Gotti on numerous charges, including Castellano's murder.
The New York Times reported at the time that "Gotti maintained a fixed smile as he stared at his former friend and trusted aide" during Gravano's testimony.
That testimony helped Gotti earn a life sentence in prison, where he died in 2002.
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