- Award Snub: Many felt that Johnny Depp would get an Academy Award nomination and were surprised when his name was left off the list of nominees. Some believe it was because Depp commented that he didn't want to win an Oscar if nominated for one. He was nominated for the SAG Award for Best Actor and won the Desert Palm Achievement Award at the Palm Springs International Film Festival.
- Harsher in Hindsight: The real Whitey Bulger, who was known for his feud with the Italian Mafia and informed on them to the the FBI, was beaten to death inside prison by a Mafioso and his associates in 2018, for being a "rat". And Bulger's death wasn't quick either - his eye had been gorged out and his tongue had been severed.
- Just Here for Godzilla: While seen as a decent film, most agree that the main reason to watch it is for Johnny Depp's performance, which was seen by many as a return to form.
- Moral Event Horizon: Bulger does many disgusting things in the film, but at least it was confined to Boston's underworld. However, when he personally strangles a young prostitute to death (who was his right-hand man's girlfriend/stepdaughter) even though he doesn't even know if she snitched on him, he just decided she knew too much. He shows zero remorse for his crime and just refers to her as "the whore" when bringing her up later in the movie.
- Nightmare Fuel: Most of the death scenes.
- Signature Scene: The "family secret" dinner scene.
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