Winston: All right, genius, since you know me so well, what am I thinking right now?
Christopher: Well, you're worried because we're going to see somebody who's not exactly my biggest fan. You're second guessing.
Winston: "Not exactly your biggest fan." The man told you if he ever saw you again, he'd shoot you you in the kneecaps, stuff you in a steamer trunk, and sink it to the bottom of the bay.
Christopher: You see, that's what I'm talking about. You're nervous.

Winston: He wants to kill you, and you just want to, just waltz into his living room. But, see, I've been around you long enough to know that, for you, that's pretty much par for the course
Christopher: Still, you come along. You're like a... mystery wrapped in a riddle wrapped in... cashmere.

Tony Belvilacqua: Your client doesn't sound too smart.
Christopher: I'll be honest with you. He's not the brightest bulb in the box.
Eddie Dunn: Is he saying I'm dumb?
Guerrero: Of course not.
Eddie Dunn: I'm not dumb.
Guerrero: Your headphones are on backwards.

Guerrero: I think we just won the fight. The pop you heard was Emil's wrist.
Eddie Dunn: How do you know what a broken wrist sounds like?
Guerrero: Practice.

Winston: Well, I don't care what he says. Till this yips things gets figured out, I'm not taking any chances. We're gonna fix his next fight. What?
Guerrero: And you call yourself a role model?
Winston: Huh.

Guerrero: The commissioner and I have a relationship.
Eddie Dunn: What kind of relationship?
Guerrero: The kind where I get a monthly stipend. Certain photos stay stashed away in a drawer, and he stays happily married.

Hugh Prentiss: Where is Eddie Dunn?
Christopher: Well, that depends. If you ask Descartes, he'd say that his mind and his body can exist in two places at the same time. If you ask Jung, he'd say that he's in our unconscious realm. Keep asking whoppers like that, we're gonna be here for a while.

Winston: You want to know why I come with you on these things? It's not because I'm nervous. it's not because I want to second-guess you, and it's definitely not because I'm some sort of... closet thrill junkie. I come with you on these things because... You know.
Guerrero: For god's sake, get a room already.
Winston: Oh, shut up.