When the FBI (Kevin Bacon headed this branch), wanted to bust the Italian mafia that was taking over the Boston streets, FBI agent John Connolly turned to his old boyhood friend Jimmy “Whitey” Bulger and asked him to be the FBI informant. As a “business deal” it made sense … after all, the Italian mafia was infringing on Whitey’s territory, and so he agreed.
Johnny Depp (in heavy makeup) portrayed James “Whitey” Bulger with perfectly measured depravity and very little redeeming virtue. Aside from a brief show of possessive love for his young son (who died tragically from a rare disease – the mother of his child played by Dakota Johnson), Whitey’s playfully-kind treatment of his mother (who overlooked that he had spent more than 9 years in prison), and his respect for his brother (a powerful State Senator), there was no character development to explain why Whitey was a psychopath. The only explanation, narratively given, was that on the streets of South Boston, the children played cops and robbers. As adults, some grew up to be cops and others robbers/bad guys.
The movie focused on one gruesome execution after another, gun shots to the head, vicious beatings and strangulations, of anyone Whitey feared might betray him. The FBI, specifically agent John Connolly, looked the other way. Then Whitey disappeared from the scene.
Because this story is true, if you are familiar with the case or read the book, the ending … James “Whitey” Bulger found 12 years later living in Santa Monica, CA, was anticlimactic. However it was a real-life extraordinary example of twisted loyalties (and moral values) when those who had been involved with him (and survived) turned State’s evidence for their own lighter sentence.
Johnny Depp’s portrayal was genuinely believable (and his makeup incredible), as was all the other actors who played “despicable”. Based on the book by Dick Lehr and Gerard O’Neill, this is a fascinating story about people you’d rather not know.