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In late-1970s Boston, the FBI are looking to break the Mafia's hold on the north of the city. Agent John Connolly (Joel Edgerton) is on the case and willing to go to any lengths to achieve his aims. A South Boston native, he decides to "ally" the FBI with South Boston crime kingpin James "Whitey" Bulger (Johnny Depp), as his main enemies are the Mafia. Approaching Bulger via his brother Billy Bulger (Benedict Cumberbatch), a Massachusetts State Senator, Connolly is successful in gaining Bulger as an informant and ally against the Mafia. However, this alliance only emboldens Bulger in his quest for power and wealth, as he is able to operate with impunity and utter ruthlessness. Not realizing he is being duped, Connolly finds himself backing Bulger rather than law, order, and justice.

This Martin Scorsese film depicts the Janus-like quality of Las Vegas--it has a glittering, glamorous face, as well as a brutal, cruel one. Ace Rothstein and Nicky Santoro, mobsters who move to Las Vegas to make their mark, live and work in this paradoxical world. Seen through their eyes, each as a foil to the other, the details of mob involvement in the casinos of the 1970s and '80s are revealed. Ace is the smooth operator of the Tangiers casino, while Nicky is his boyhood friend and tough strongman, robbing and shaking down the locals. However, they each have a tragic flaw--Ace falls in love with a hustler, Ginger, and Nicky falls into an ever-deepening spiral of drugs and violence.