Years ago, a powerful Irish mafia figure [Nicholson] placed a small selection of his youngest, brightest men into the Massachusetts Police Academy as cadets. Their purpose is to eventually rise within the prestigious ranks of the city's police department, to serve as the eyes and ears of their boss. While somewhere else, a young cadet [DiCaprio] was assigned with an equally dangerous task: infiltrate the Irish syndicate headed by the man sending in his own to the Boston Police. Now, one cadet [Damon] is an up and coming police official with a torn allegiance to his job and to the criminal mastermind that put him there. While the other cadet is the trusted number two of that man, only finding his professional duties are becoming blurred with his current state. But new clues have lead to unfortunate discoveries, when both sides realize they're being watched by the enemy. It's now all just a matter of time before the men assigned to find out whose the infiltrator, could come to a bloody end when someone's identity may be revealed.I really dislike this plot summary but it's close enough to serve. For the record, Damon isn't really torn but DiCaprio is. The movie focuses on DiCaprio as he infiltrates Nicholson's cadre to try and take him down. Meanwhile, Damon is on the other side, having infiltrated the police to stymy their efforts against Nicholson. Both sides are looking for the traitor within their midst and it's only a matter of time before things come to a head.
This is an excellent movie. It's tense and, at times, bloody, but it's a great look at the pressures of undercover work. DiCaprio lives in constant fear of being discovered. Damon often fears that he might let down Nicholson. It's a fascinating game that goes round and round right up to the end. I rather enjoyed it. I recommend this movie to anyone not turned off my excessive violence and/or bloodshed. I mean, c'mon - this is from the same director who brought us Goodfellas, Casino, Bringing Out The Dead and Gangs Of New York. (I'm not mentioning Taxi Driver or Raging Bull because I haven't seen them. I know, heresy.)
Go see this movie.