In 1988 in Brooklyn, New York, Bobby Green (Joaquin Phoenix) is the manager of the successful El Caribe nightclub in Brighton Beach that is frequented by Russian black market gangster and drug lord Vadim Nezhinski (Alex Veadov), and owned by Marat Buzhayev, Vadim's uncle and Bobby's boss.
Bobby has distanced himself from his father, NYPD Deputy Chief Burt Grusinsky (Robert Duvall), and his brother, Captain Joseph Grusinsky (Mark Wahlberg). He uses the maiden name of his mother, Carol Green, as his last name, preferring to remain on the sidelines and enjoy a hedonistic life with his girlfriend Amada Juarez (Eva Mendes) and best friend Louis "Jumbo" Falsetti (Danny Hoch).
When Joseph leads a police raid on El Caribe in the hopes of arresting Vadim, Bobby refuses to cooperate. The incident strains Bobby's relationship with his father and brother even more, to the point that Bobby and Joseph come to blows.