Just before 5:30 on a December evening in 1985, mob boss Paul Castellano stepped out of a limo in front of Sparks Steakhouse in midtown Manhattan and was shot to death. The four assassins who gunned him down were conspicuously dressed in trench coats and Russian fur hats. John Gotti, the man who arranged the hit, sat in a car nearby to make sure “Big Paul” was dead.

“It was daring in the sense that it was done in Manhattan, in the Christmas season, early in the evening,” says Howard Blum, author of Gangland: How the FBI Broke the Mob. “They planned it like a military operation.”

The 70-year-old Castellano was the reputed boss of the Gambino crime family, a decades-old Mafia family in New York City. Gotti was a 45-year-old member of the Gambino family who didn’t like boss Castellano’s recent instruction not to trade in drugs. Castellano was worried the federal government was paying too much attention to their drug activities.

Gotti ignored Castellano’s edict and continued to have his people trade heroin. But because the federal government was watching, news of wiretaps showing Gotti and his associates were still dealing drugs became public.

“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.

One of the important witnesses in the 1992 conviction was Salvatore Gravano, a former member of the Gambino family. He testified that he sat in the car with Gotti during Castellano’s assassination and that they used walkie-talkies to notify the gunmen when Castellano’s limo was approaching.

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.

Blum says that after 9/11, the federal government and the media became less focused on the mob, which continued to operate in the shadows. But it stepped back into the spotlight in March 2019, when Frank Cali, another reputed Gambino boss, was executed in a hail of gunfire outside his home in Staten Island. The murder marked the first assassination of a New York City mob boss since Castellano’s.

"We thought those days were over,” New York City mayor Bill de Blasio said at a press conference after Cali's murder. “Very surprising, but I guess old habits die hard."