Black Mass is the Real Life story of infamous Boston crime kingpin Whitey Bulger. The story starts in 1975 with James "Whitey" Bulger (Depp) already the chief of the Irish mob in south Boston. Bulger's Winter Hill gang is fighting a turf war with the Angiulo Brothers, an Italian crime gang which is trying to muscle out Bulger's gang in order to take control of organized crime in Boston. FBI Agent John Connolly (Edgerton) a native of Boston and friend of Bulger since childhood, comes up with an idea: Bulger will inform on the Italian mafia for Connolly, which will allow Connolly to bust the Italians and will make things easier for Bulger. Eventually Connolly does bust the Italian mob in Boston, but in the process gets in way too deep with Bulger, protecting him from prosecution and effectively becoming Bulger's mole within the FBI as Bulger becomes the most notorious gangster in Boston history.
Tropes:
- Affably Evil: Whitey is quite charming at times. Most of the time he's closer to Faux Affably Evil though, especially after his son and mother die.
- Arms Dealer: The biggest (attempted) donation of weapons to the IRA came from Bulger's gang.
- Bait the Dog: Whitey appears to give Flemmi's stepdaughter, Deborah, a large apartment for her to stay in and she nearly starts tearing up as she notes that nobody has ever done anything so kind for her before. He then strangles her to death and makes it abundantly clear he could not care less about murdering her.
- Based on a True Story: More or less, but many changes were made for the film.
- Whitey's son actually died well before the time period of the movie.
- The scene where Whitey not-so-subtly threatens Connolly's wife is an invention.
- The newspaper article about Bulger being an informant actually came out several years before Bulger fled town and Connolly was arrested. It was met with broad skepticism in Boston and Connolly continued to work for the FBI for quite a while after.
- In the movie Howie Winter is nowhere to be seen and Bulger is already running the Winter Hill gang in the mid-1970s. In Real Life Howie Winter wasn't arrested until 1979.
- Believing Their Own Lies: Connolly seems to honestly believe his claims that Bulger is a valuable informant to the FBI. It becomes increasingly clear that Connolly is deluding himself.
- Beauty Inversion: To play Bulger, Depp wore extensive prosthetics and makeup, and is barely recognizable as a result.
- Boom, Headshot!: Whitey, Weeks, Flemmi, and a Mook go out walking. The mook apologizes for an argument in which said mook raised his hand and threatened Whitey. Whitey accepts the apology, and then Flemmi casually shoots the mook in the back of the head.
- Cluster F-Bomb: Considering it takes place in Boston, the very liberal usage of the word "fuck" by almost every character is not surprising. There's 254 uses of the F-word in total.
- Conflicting Loyalty: Connolly never does seem to figure out that being pals with Whitey Bulger does not work well with being an FBI agent.
- Death of a Child: Whitey's little boy dies of Reye syndrome.
- Dirty Cop: No cops are actually shown taking bribes, but Connolly winds up in Bulger's pocket. There's also a beat cop who delivers messages to Bulger on behalf of the Italian mob. It's stated Bulger's gang paid off many, many more too.
- Disc-One Final Boss: The Angiulos are the initial main villain for the FBI to defeat in order to free Boston from their reign of crime, but by the time the Winter Hill Gang helps to arrest them, they take center stage as the main villains by spring of 1982.
- Even Bad Men Love Their Mamas: Whitey is a multiple murderer and a monstrous sociopath, but he is a dutiful son who comes home to play gin with his mom.
- Even Evil Has Loved Ones: Bulger's a murderous crime boss. He's also an affectionate father to his little son.
- Even Evil Has Standards:
- Whitey is so evil he is almost reptilian, but even he is grossed out by the fact that Flemmi is dating his stepdaughter, who called him "Daddy" when she was a child. Interestingly this trope gets flipped on its head when Whitey kills her because he thinks she knows too much while Flemmi looks on sorrowfully, making Whitey look even more depraved than Flemmi.
- A Played more straight example at the beginning of the movie is when he berates Johnny Martorano for putting his dirty hands into more Triple O's bar nuts after eating the current batch he put in his mouth.
- Evil Laugh: Whitey lets out a very intimidating cackle during the dinner scene after he not so subtly threatens Connolly's partner.
- Faux Affably Evil: Bulger is at least flirting with this trope at the start of the movie but embraces it more fully as time goes on.
- Gray Rain of Depression: When Connolly comes home to find out that his wife has changed the locks, it's pouring rain.
- He Knows Too Much:
- The Winter Hill Gang have Roger Wheeler murdered because he was snooping in John Callahan's World Jai Alai business note after he bought the franchise.
- In possibly the most disturbing scene in the movie, Bulger strangles Flemmi's stepdaughter/girlfriend Deborah to death, as Deborah has been busted for prostitution and Whitey fears she will blab what she knows about his crimes.
- Historical Hero Upgrade: The portrayal of Robert Fitzpatrick is that of a straight hero, while the real Fitzpatrick was eventually convicted of perjury and obstruction of justice in relation to the case against Bulger and it was found that much of his story, including facing retaliation at the FBI for trying to blow the whistle on Bulger, was made up.
- Historical Villain Downgrade: According to the Real Life Kevin Weeks, the portrayal of Flemmi was this. "Stevie wasn’t all sympathetic, mourning, and sorrowful like he is in the movie. Stevie enjoyed murder." [1]
- The Informant: Whitey pretends to be one, but other than tipping Connolly to the location of the Italian mafia's headquarters, he never tells the FBI anything they don't already know. Connolly later turns away a real informant who wanted to tell the FBI about Bulger's responsibility for the Wheeler murder. Whitey later murders McIntyre, a real informant who tipped the FBI to Whitey's involvement in the arms smuggling to the IRA.
- Interrogation Flashback: The film is told in flashbacks by Stephen Flemmi and Kevin Weeks, two of Whitey Bulger's Mooks as they're being interrogated. The ending reveals that they're only doing so after Bulger was exposed as an FBI informant.
- The Irish Mob: Bulger's gang, which runs organized crime in Boston. They are very conscious of their ethnic identity, with Bulger running guns to the IRA.
- The Mafia: The regular old Italian mafia, fighting Bulger for control of crime in Boston, and losing, thanks to the assist of Connolly and the FBI.
- Mob War: Between Bulger and the Angiulo brothers for control of Boston. Bulger wins, after helping the FBI to find the Italians' hideout in Boston.
- The Mole: Bulger isn't much of one, as it turns out almost everything he told the FBI was stuff they already knew.note Connolly eventually becomes a much straighter example of a mole, as he winds up being Bulger's man inside the Bureau.
- Morality Chain: For Whitey, his son and his mother (to a lesser extent, little old ladies from the Old Neighborhood in general). Once they've both died later in the film, it's mentioned he was never the same, and the only time he was seen to smile afterwards was when he was talking about the IRA.
- Officer O'Hara: If you'd expect to find one anywhere, you'd expect to find one in Boston. A beat cop with a strong accent delivers a message to Bulger on behalf of the Italian mob.
- Outliving One's Offspring: The death of Whitey's son marks a point when he becomes even more ruthless.
- Parental Incest: Flemmi is dating his stepdaughter. Whitey is grossed out.
- Punk in the Trunk: After Callahan, Whitey's man inside World Jai Alai, outlives his usefulness, Martorano kills him and stuffs Callahan's body in the trunk of his own car.
- Sibling Yin-Yang: Whitey Bulger is a murderous crime kingpin. His brother Billy (Cumberbatch) is not only a straight arrow, he's a politician and an 18-year veteran of the Massachusetts legislature.
- The Sociopath: Bulger is described as this multiple times, though they use the word "psychopath" instead, which if anything is worse.
- Villain Protagonist: Whitey Bulger of course. And a horribly evil villain at that, who's pretty much only redeeming value is that he does seem to care about his close family members.
- What the Hell, Hero?: Connolly's wife Marianne tells him that he might be getting in too deep with Bulger. Then she tells him again, more forcefully, when Connolly actually has Bulger over for dinner. After Connolly doesn't listen, and after Bulger threatens her directly, Marianne divorces Connolly.
- "Where Are They Now?" Epilogue: The standard graphics at the end noting the fates of all the characters. Bulger was caught in 2011 after 16 years on the run and was convicted of murder with multiple life term sentences. Connolly was convicted of 2nd-degree murder in the death of Halloran and was sentenced to 40 years.
- Would Hit a Girl: Bulger killed Flemmi's stepdaughter and made a death threat against Connolly's wife.
- Would Hurt a Child: As stated above, Bulger killed Flemmi's stepdaughter, who was 14-years-old.
