In 1949 Los Angeles, gangster Mickey Cohen (Sean Penn) wants to control all organized crime, arguing with local mobster Jack Dragna (Jon Polito) that they should not allow the East coast Mafia to run the town.
Los Angeles Police Department (LAPD) Detective Sergeant John "Sarge" O'Mara (Josh Brolin) busts into a Cohen brothel to save a woman, newly arrived to Hollywood, from Cohen's thugs. Chief Bill Parker (Nick Nolte), impressed that O'Mara had knowingly raided a Cohen operation – and aware that O'Mara has special operations background and training at Camp X
during World War II – tasks O'Mara to wage guerrilla warfare against
Cohen, and appoints him to choose a small team that must work in
anonymity, with no badges and no LAPD support.
O'Mara's pregnant wife Connie (Mireille Enos)
suggests choosing unorthodox veterans like himself, as young
high-performers are probably already on Cohen's payroll. With Connie
helping him to review personnel files, O'Mara selects a small squad of
cops: Coleman Harris (Anthony Mackie) is a black cop who wants to cut off the heroin flow to Central Avenue, wiretapper and family man Conwell Keeler (Giovanni Ribisi) wants his son to know that he fought to make a difference, old timer and gunslinger/sharpshooter Max Kennard (Robert Patrick) and his young Hispanic partner Navidad "Christmas" Ramirez (Michael Peña) do not fit in well with the regular force and want in.
O'Mara fails in an attempt to recruit Sgt. Jerry Wooters (Ryan Gosling), a corrupt detective who prefers to do the minimum in his daily job. Wooters keeps in touch with childhood friend Jack Whalen (Sullivan Stapleton), an informant with some connections to Cohen. Grace Faraday (Emma Stone) is Cohen's girlfriend and etiquette coach. Wooters and Grace begin a secret love affair, protected by a reluctant Whalen.
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