Set in Brooklyn circa 1985 against the backdrop of John Gotti’s rise to power, the film revolves around three lifelong friends whose different ambitions threaten to shake their enduring bond. Michael, the narrator, is a lovable charmer with the soul of a con man who successfully scams his way into the pre-law program at Columbia University. In contrast to Michael’s desire to leave the Brooklyn streets behind, his close friend Carmine, a handsome lady-killer enamored of the Mafia lifestyle, wants nothing more than to stay there. And rounding out the trio is Bobby, an endearing cheapskate who longs for a simple life of working at the Post Office and settling down with his fiancée. While at Columbia, Michael falls for a beautiful young student named Ellen, a society girl whom he initially wins over with his preppy schoolboy cover. As their relationship blossoms, leaving the streets behind seems increasingly possible, but when Carmine catches the eye of Caesar, a feared mobster who controls their Brooklyn neighborhood, Michael and Bobby are drawn into that world despite their reluctance to get involved.