Officer Flynn: You threatening me, Bulger?
Whitey Bulger: The last thing I would do if I was planning to harm you was to warn you in advance, you dumb fuck.
Officer Flynn: You better watch yourself, Bulger.
Whitey Bulger: You better fuck yourself, Flynn.
John McIntyre: I told him everything! The IRA, Cahill, the whole bit! I know I shouldn't have, Jimmy, but I had no choice.
Whitey Bulger: Fuck you. You always have a choice. You just happened to make the wrong fucking one.
Whitey Bulger: Take your shot, but make it your best. 'Cause I get up, I eat ya.
Fred Wyshak: How come no-one has nailed Whitey Bulger? He seems to be involved in every crime in the city, and yet the Bureau keeps saying he's clean.
John Connolly: Well, what's Bulger done?
Fred Wyshak: What's he done? Everything.
John Connolly: Thank God for Whitey Bulger.
Whitey Bulger: Just make him an offer for the company.
John Callahan: I tried. Won't sell.
Whitey Bulger: Would his widow sell?
John Connolly: Like it or not, Marriane, you married a street kid. And the streets taught me that you give and you get loyalty from your friends. And loyalty means a lot to me.
Mrs. Cody: Jimmy! When did you get out of Alcatraz?
Whitey Bulger: Oh, uh, that's nearly ten years ago.
Kevin Weeks: In the beginning, Jim was a small time player. He really only mattered in Southie. Don't get me wrong, he was a tough motherfucker, but small time. And the next thing you know, he was a goddamn kingpin. You know why? Because the FBI let it happen.
John Connolly: I'm not asking you to help me. I'm asking you to help your brother.
Billy Bulger: That's the same thing now, isn't it?
