Tommy working out his assassination?
- When Tommy and the two made men enter the "initiation room", what clued Tommy at the very last moment that he wasn't going to be made at all?
- The fact that the room was empty. If he'd actually been there to be made, there'd have been a group of guys there to welcome and congratulate him before the ceremony began.
- Also, at the very least, maybe some food and drink, a nice comfy chair to sit in, some music. Not just a card table with nothing on it.
Why weren't the robbers more careful?
- How could they just start buying expensive stuff with the money they stole in the aftermath of their robbery? No wonder Jimmy decided to kill them (although that may have come to him eventually), no one can be that careless.
- As was stated throughout the film, this was the single biggest heist in history at the time. These guys were feeling like kings of the world, untouchable, and exulting in victory. This of course led to recklessness born of avarice and arrogance. These men are greedy and reactionary: why do you think they became gangsters in the first place?
- Stupid Crooks? It's very common for criminals to spend their ill-gotten gains lavishly, hence why so many end up getting caught.
Jimmy and Henry's involvement in the Batts murder
- Tommy was murdered in retribution for killing Billy Batts, who was a made man and not supposed to be killed without permission. Yet Jimmy and Henry also participated in Batts' murder, so why was there never any mob retribution against them?
- The Powers-That-Be knew Tommy was half-crazy. OTOH Jimmy and Henry were steady guys and good earners, so they figured Tommy was enough.
The Pink Cadillac Hit
- Having recently watched the movie for the first time, one thing that stuck out to me was the lack of bullet holes in the pink Cadillac after Johnny and his wife are murdered in it. Their bodies are clearly all shot up, but there aren't any bullet holes in the car, either from the inside or outside. In a movie as well-crafted as this, that struck me as jarring.
- They may have been killed by someone inside the car, which explains the blood splattered all over the inside. As seen with what happened to Morrie, bullets wouldn't be needed.