Summery:
The true story of Whitey Bulger, the brother of a state senator and the most infamous violent criminal in the history of South Boston, who became an FBI informant to take down a Mafia family invading his turf...............
Director: Scott Cooper
Writers: Mark Mallouk (screenplay), Jez Butterworth (screenplay), 2 more credits
Stars: Johnny Depp, Benedict Cumberbatch, Dakota Johnson
Story-line
John Connolly and James "Whitey" Bulger grew up together on the streets of South Boston. Decades later, in the late 1970s, they would meet again. By then, Connolly was a major figure in the FBI's Boston office and Whitey had become godfather of the Irish Mob. What happened between them - a dirty deal to trade secrets and take down Boston's Italian Mafia in the process - would spiral out of control, leading to murders, drug dealing, racketeering indictments, and, ultimately, to Bulger making the FBI's Ten Most Wanted List.
Plot:
In 1975, James "Whitey" Bulger, a small-time gangster and leader of the Irish-American Winter Hill Gang, controls almost all of organized crime within South Boston, along with his right-hand man Stephen Flemmi, newcomer Kevin Weeks, and cold and calculative hitman, Johnny Martorano. Bulger's hold over South Boston is challenged by the northern Angiulo Brothers, who are the Boston branch of the Patriarca crime family.
An interesting opportunity arises with the return of John Connolly to South Boston; Connolly being a former native of the area and friend of Whitey and his brother, Massachusetts State Senate President William "Billy" Bulger. Connolly's advancement within his position in the Federal Bureau of Investigation (FBI) pressures him into attempting to find a way to go after the Angiulo Brothers, who are continuing to avoid police detection. Connolly tries to persuade Billy into getting Whitey to cooperate with the FBI, but Billy refuses him yet gives notice to Whitey. Whitey detests of the idea of going "rat" for the police, but feels the pressure on himself as he wishes to protect both his wife, Lindsey, and son, Douglas. After the Angiulo Brothers murder a member of the Winter Hill gang, Whitey decides to become an informant, much to Flemmi's dismay.
However, Connolly's control over Whitey is continually questioned by his boss, Charles McGuire, although he is also defended by his close co-worker, John Morris, who blindly follows Connolly's plan.
Tensions increase as Whitey ignores the FBI ban on criminal activity or murders, using Connolly's "protection" as a cover for his crimes. He becomes unhinged however, when his son Douglas suddenly develops Reye syndrome after having a severe allergic reaction to aspirin. After being told that Douglas will spend years in a vegetative state, Lindsey takes him off life support over Whitey's objections. Their relationship breaks off afterward, just as Connolly begins demanding actual information on the Angiulos' racketeering locations. Finally, Whitey is able to get pictures of their work hideouts, allowing the FBI to wiretap the Angiulos head-on.
Before McGuire can terminate the informant operation, the wiretaps pick up the Angiulos discussing their criminal activities. The FBI arrests them--unwittingly eliminating any opposition to Whitey's criminal empire. Connolly, blinded by his old past and loyalty to Whitey, grows closer to him and the gang as their relationship goes beyond a simple agent-informant relationship. His wife, Marianne, is disgusted by their presence at home, but is forced to deal with them and her husband's further change.
Problems rise later on as Whitey is suddenly cut out of an embezzlement scheme from World Jai Alai. He directs Martorano to murder the oncoming owner, Roger Wheeler, and their original embezzlement contact, John Callahan. Whitey suspects that an associate who overhears the murder plan, Brian Halloran, would not keep it a secret, so he pays him off to leave. Halloran later hears about Wheeler's murder. Fearing for his life, Halloran goes to the FBI to report Bulger's involvement in the crime. Connolly and Morris dismiss Halloran's accusations against Bulger due to his cocaine addiction and refusal to take a polygraph. Connolly, fearing Whitey is in too deep, tells Whitey of Halloran's accusation. Whitey then hunts down and murders Halloran and an unnamed friend of his in broad daylight soon after.
Whitey's informant relationship deteriorates due to his increasingly violent behavior - threatening Morris and Marianne, as well as murdering Flemmi's prostitute stepdaughter, Deborah Hussey. Ultimately, the downfall begins with the appointment of "bulldog" prosecutor Fred Wyshak as U. S. Attorney. Connolly attempts to make friends with Wyshak, who coldly refuses and also scolds Connolly for his idiotic relationship with Whitey. He demands that the FBI take down Whitey. When John McIntyre, an informant within the Winter Hill Gang itself, blows the whistle on Whitey's attempt to smuggle weapons for the Provisional Irish Republican Army, he is brutally beaten and garroted by Whitey--most likely due again to Connolly's inside information. Wyshak and McGuire investigate Connolly's control over Whitey's informant activity. They discover that most of what Connolly presented as Whitey's tips were actually repeats of earlier tips from low-level informants. Morris reveals the true nature of Connolly and Whitey's relationship to The Boston Globe.
Whitey is forced to acknowledge the end when The Globe publishes a front-page article about his informant activities, which causes him to lose the gang's trust. In the final scenes, Connolly, Flemmi, Weeks, and Martorano are arrested. Whitey goes on the run, but not before giving Billy a final goodbye from a pay phone. Morris turns state's evidence and testifies against Connolly in return for immunity for his role in their crimes. After Connolly's and the other characters' sentences are shown, a final scene reveals Whitey being finally caught by the FBI in 2011, 16 years after the initial crackdown.
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