After killing Pretty Boy Floyd (Channing Tatum), Federal Bureau of Investigation agent Melvin H. Purvis (Christian Bale) is promoted by J. Edgar Hoover (Billy Crudup) to lead the hunt for John Dillinger, declaring the first national "War on Crime". Purvis shares Hoover's belief in using scientific methods to battle crime, ranging from cataloging fingerprints to tapping telephone lines.
In between a series of bank robberies, Dillinger meets Billie Frechette (Marion Cotillard) at a restaurant and woos her by buying her a fur coat. Frechette falls for Dillinger even after he reveals his identity, and the two become inseparable.
Purvis leads a failed ambush at a hotel where he believes Dillinger is staying; an agent is killed by Baby Face Nelson (Stephen Graham), who escapes with Tommy Carroll (Spencer Garrett). Purvis requests that Hoover bring in professional lawmen who know how to catch criminals dead or alive, including Texas "cowboy" Charles Winstead (Stephen Lang).
Police find Dillinger and arrest him and his gang in Tucson, Arizona, after a fire breaks out at the Hotel Congress. Purvis arrives that evening and talks with Dillinger, who is extradited to the Lake County Jail in Crown Point, Indiana, where he is locked up by Sheriff Lillian Holley (Lili Taylor) pending trial. Dillinger and other inmates use a fake gun to escape the jail. Dillinger is unable to see Frechette, who is under tight surveillance. Dillinger learns that Frank Nitti's (Bill Camp) Chicago Outfit associates are unwilling to help him because Dillinger's crimes are motivating the federal government to prosecute interstate crime, which imperils Nitti's bookmaking racket.
Carroll goads Dillinger into a bank robbery in Sioux Falls with Baby Face Nelson. Despite thinking Nelson hasn't the discipline for his style of robbery, Dillinger participates. As feared, Nelson fires on those in the bank; during their escape, both Dillinger and Carroll are shot, the latter fatally, and they have to leave him behind. The group retreat to the Little Bohemia Lodge in Manitowish Waters, Wisconsin, and realize their haul is significantly less than Nelson said it would be. Dillinger hopes he can free the rest of his gang from prison, including Pierpont and Makley, but Red convinces him this is unlikely.
Purvis and his men apprehend Carroll and torture him to learn the gang's location. Purvis organizes an ambush at Little Bohemia. Dillinger and Hamilton escape separately from Nelson and the rest of the gang. Agents Winstead and Hurt (Don Frye) pursue Dillinger and Hamilton through the woods, engaging them in a gunfight in which Hamilton is fatally wounded. Trying to escape along the road, Nelson, Shouse and Van Meter hijack a Bureau car, killing Purvis's partner Carter Baum (Rory Cochrane) in the process. After a car chase, Purvis and his men kill Nelson and the rest of the gang. Hamilton dies that night and Dillinger buries his body.
Dillinger meets Frechette, telling her he plans to commit one more robbery that will pay enough for them to escape together. When Dillinger drops her off at a tavern he thinks is safe, she is captured by law enforcement. Frechette is beaten during an interrogation to learn Dillinger's whereabouts, which she does not reveal; Purvis and Winstead stop the interrogation. Dillinger meets with Alvin Karpis (Giovanni Ribisi), who tries to recruit Dillinger in a train robbery with the Barker Gang. Dillinger agrees to participate and intends to flee the country the next day. Dillinger receives a note from Billie through her lawyer, Louis Piquett (Peter Gerety), telling him not to try to break her out of jail, but to wait until she is released to start a new life together.
Through Zarkovich, Purvis enlists the help of madam and Dillinger acquaintance Anna Sage (Branka Katić), threatening her with deportation if she does not cooperate and uses her as his spy. She agrees to set up Dillinger, who she believes will come to hide out with her. Dillinger and Sage see Manhattan Melodrama at the Biograph Theater. After the film, Purvis signals other agents upon seeing them leave. Dillinger spots the police but is shot multiple times before he can draw his gun. Winstead, who shot Dillinger through the head, listens to Dillinger's last words. Purvis departs to inform Hoover of Dillinger's death.
Winstead tells Frechette, still incarcerated, that he thinks Dillinger's dying words were, "Tell Billie for me, 'Bye bye Blackbird.'" The closing text reveals that Melvin Purvis quit the Federal Bureau of Investigation in 1935 and died by his own hand in 1960, and that Billie lived out of the rest of her life in Wisconsin following her release in 1936.
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