Mafia boss Paul “Big Paulie” Castellano (1915 – 1985) was head of NYC’s Gambino crime family from 1976 until his passing. The son of a mobster in the Mangano family – forerunner of the Gambinos – who ran a numbers game, Castellano dropped out of school in eighth grade to become a hoodlum. By the 1950s, he had risen to become a capo. Although up to his neck in mob rackets, Castellano acted as if he was a legitimate businessman – an affectation that annoyed many of his hoodlum underlings, who had no delusions about their careers.
The disgruntled underlings of the Gambino boss included an ambitious capo named John Gotti. When Castellano failed to attend a prominent subordinate’s funeral in 1985, it offended many Gambinos, and disgruntlement soon grew into rebellion. On December 16th, Gotti organized a hit squad that waited for Castellano’s outside one of his favorite restaurants, Sparks Steak House, in midtown Manhattan. As Castellano exited his car, Gotti watched from across the street as the hitmen rushed the mob boss, and gunned him down.