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Frank "The Irishman" Sheeran is a man with a lot on his mind. The former labor union high official and hitman, learned to kill serving in Italy during the Second World War. He now looks back on his life and the hits that defined his mob career, maintaining connections with the Bufalino crime family. In particular, the part he claims to have played in the disappearance of his life-long friend, Jimmy Hoffa, the former president of the International Brotherhood of Teamsters, who mysteriously vanished in late July 1975 at the age of 62.

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.

Henry Hill might be a small time gangster, who may have taken part in a robbery with Jimmy Conway and Tommy De Vito, two other gangsters who might have set their sights a bit higher. His two partners could kill off everyone else involved in the robbery, and slowly start to think about climbing up through the hierarchy of the Mob. Henry, however, might be badly affected by his partners' success, but will he consider stooping low enough to bring about the downfall of Jimmy and Tommy?