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That's not even the stupidest part of The Departed(DiCaprio's actions at the police station after he figures out Damon is the mole), but I don't think plot holes really qualify.

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I do not think that any of the plot holes up until that point are really that big or more noticable then any other movie. The problem was that the actions from this point on from ever character in the movie just make no sense and it kind of just kills it. I also really think the final scene should of have involved damon/leo figuring out who each other is was and [censored] while like in the presence of the girl or something.