History Film / BlackMass

* EvenEvilHasStandards: 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 [[InvertedTrope flipped on its head]] when [[spoiler: Whitey kills her because he thinks she knows too much while Flemmi looks on sorrowfully, making Whitey look even more depraved than Flemmi.]]

* HeKnowsTooMuch: In possibly the most disturbing scene in the movie, [[spoiler: 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.]]

* HistoricalVillainDowngrade: According to 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." [[http://www.thedailybeast.com/articles/2015/09/20/whitey-bulger-s-enforcer-slams-black-mass-the-movie-is-pure-fiction.html]]

* InterrogationFlashback: The film is told in flashbacks by 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.

* PunkInTheTrunk: After Callahan, Whitey's man inside World Jai Alai, outlives his usefulness, Martorano kills him and stuffs Callahan's body in the trunk of Callahan's own car.

* ClusterFBomb: 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 fuck in total.

* YourCheatingHeart: {{Implied|Trope}}. While on a mission in a different city, the married Connolly is seen dancing in a seductive manner with another woman, but it's unclear if he actually slept with her afterwards.

** Whitey's son actually died well before the time pe of the movie.

* InfantImmortality: {{Averted|Trope}}. [[spoiler: Whitey's little boy dies of Reye syndrome.]]

* EvenBadMenLoveTheirMamas: Whitey is a multiple murderer and a monstrous sociopath, but he is a dutiful son who comes home to play gin with his mom. He's also an affectionate father to his little son.

** Whitey's son actually died well before the time frame of the movie.

* FramingDevice: Bulger's henchmen Flemmi and Weeks being interviewed by the feds, telling all about Bulger's criminal history. [[spoiler:The ending reveals that they are doing this only after Bulger has skipped town.]]

* YourCheatingHeart: {{Implied|Trope}}. While on a mission in a different city, the married Connolly is seen dancing in a seductive manner with another woman, but it's unclear if he actually slept with her afterwards.

* AffablyEvil: Whitey is quite charming at times. Most the time he's closer to FauxAffablyEvil though, especially after his son and mother die.

* SiblingYinYang: 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.

* WhereAreTheyNowEpilogue: The standard graphics at the end noting the fates of all the characters. [[spoiler: 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.]]

* WouldHurtAChild: As stated above, Bulger killed [[spoiler:Flemmi's stepdaughter, who was 14-year-sold.]]

* InfantImmortality: {{Averted}}. [[spoiler: Whitey's little boy dies of Reye syndrome.]]

* MoralityPet: For Whitey, his son and his mother (to a lesser extent, little old ladies from the Old Neighborhood in general). [[spoiler: 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.]]

* WhereAreTheyNowEpilogue: The standard graphics at the end noting the fates of all the characters. [[spoiler: 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.]]

* MoralityPet: 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.

** 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.

* BeautyInversion: To play Bulger Depp wore extensive prosthetics and makeup, and is barely recognizable as a result.

* CaliforniaDoubling: An inversion where Revere, Massachusetts stands in for Santa Monica, California.

* BelievingTheirOwnLies: Connolly seems to honestly believe his claims that Bulger is a valuable informer to the FBI. It becomes increasingly clear that Connolly is deluding himself.

* ClusterFBomb: 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 fuck in total.

* DirtyCop: 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.

* EvilLaugh: Whitey lets out a very intimidating cackle during the dinner scene after not so subtly threatening Connoly's partner.
* FauxAffablyEvil: Bulger is at least flirting with this trope in the start of the movie but embraces it more fully as time goes on.

* InfantImmortality: Averted. [[spoiler: Whitey's little boy dies of Reye syndrome.]]

* MobWar: Between Bulger and the Angiulo brothers for control of Boston. Bulger wins, after helping the FBI to find the Italian hideout in Boston.
* TheMole: Bulger isn't much of one, as it turns out almost everything he told the FBI was stuff they already knew[[note]]It's implied that Connolly simply took archived testimony from other informants and re-submitted them under Bulger's file to make his operation look better[[/note]]. Connolly eventually becomes a much straighter example of a mole, as he winds up being Bulger's man inside the Bureau.
* MoralityPet: 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.

* PunkInTheTrunk: After Callahan, Whitey's man inside World Jai Alai, outlives his usefulness, Flemmi kills him and stuffs Callahan's body in the trunk of Callahan's own car.

* BaitTheDog: 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.

* BoomHeadshot: 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.

* EvenEvilHasStandards: 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 [[InvertedTrope 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.

* FramingDevice: Bulger's henchmen Flemmi and Weeks being interviewed by the feds, telling all about Bulger's criminal history. The ending reveals that they are doing this only after Bulger has skipped town.

* HeKnowsTooMuch: 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.

* InfantImmortality: Averted. Whitey's little boy dies of Reye syndrome.

* OutlivingOnesOffspring: The death of Whitey's son marks a point when he becomes even more ruthless.

* WhatTheHellHero: 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.
* WhereAreTheyNowEpilogue: 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.