Character Analysis
The Protégé
Colin Sullivan is a rough guy from a rough neighborhood, which is kind of sad because he seems like such a sweet little boy when we first meet him. But from day one, he gets mentored by Frank Costello in the ways of taking whatever you want from life.
Colin seems to carry this sense of entitlement into his adult life, especially when he gets questioned about how he runs his police investigations. His answer?
COLIN: I don't have to f***ing explain anything to anybody! I can f***ing investigate anybody I want to!
When Colin's not mouthing off, he's hitting on women he meets and saying things like:
COLIN: I'II stab someone in the heart with a f***ing ice pick if it gets me dinner with you.
Actor Matt Damon has a way of making these lines seem charming, but if you look at the actual words, you find that Colin has a pretty dark sense of humor.
Unfortunately, he also kind of has a murderous streak.
In a Relationship
We find out partway through the movie that Colin doesn't really like to talk about where he comes from, which is the rough neighborhood of Southie. When his fiancée Madolyn brings childhood pictures of herself to his apartment when she moves in, he immediately takes them out of the room and says:
COLIN: You don't see any pictures of where I came from. Look, I respect who you are. Just, you know, not in the living room. We might have company.
Colin's response goes to show two things: first, that he is ashamed of his background; and second, that he doesn't want to remind anyone of anything that could connect him to his true boss, the mobster Frank Costello.
On top of his dark sense of humor and his sensitivity about his past, Colin is a typical Irish dude in the sense that he doesn't talk much about his feelings or any problems in general. At one point, he even says to Madolyn:
COLIN: If we're not gonna make it, it's gotta be you that gets out, because I'm not capable. I'm f***ing Irish. I'll deal with something being wrong for the rest of my life.
In other words, Colin's telling Madolyn that even if something were terribly wrong with their relationship, he would rather put his head down and ignore it than actually do something about it.
Flying Too Close to the Sun
At the end of the day, we know that Colin would like to keep moving up in the world. We can even tell by the way he stares at the State House that he'd like to be a big-shot politician someday—or maybe even governor. But when a friend catches him staring at the building, he says to Colin:
BARRIGAN: What are you looking at? Forget it. Your father was a janitor, his son's only a cop.
Basically, the guy accuses Colin of dreaming too big, and he tells Colin to be happy with what he's got. But Frank Costello, on the other hand, taught Colin never to be happy with what's he's got. He taught Colin to go out and take whatever he wants, and this has filled Colin with the need to always have more and more of everything—especially power.
Colin might put on a really tough face, but we find out at the end of this movie that deep down, he's just as scared as any normal person would be in his situation. He tries his best to look tough in front of Billy by saying:
COLIN: I can't wait to see you explain this to a Suffolk County jury, you f***ing cocksucker. This is gonna be f***ing fun.
But once he realizes he can't bluff his way out of the situation, Colin breaks down crying and says:
COLIN: Just f***ing kill me.
In the end, Colin escapes this situation only to get his head blown off by Sergeant Dignam later in the movie. He gets his comeuppance even though we might still feel some sympathy for him.