- Ryan O'Reily: [when asked by Busmalis, Rebadow and Hill how to choose a winner in the coming boxing match] Hey, I'm a man of logic; I'm a man of planning. I consider every detail; I factor in every possibility. Then I flip a coin.
- Margarita Ricardo: I'm here to see my brother, Carlo Ricardo.
- Officer Diane Whittlesey: Ricardo.
- [flips through pages]
- Officer Diane Whittlesey: No, sorry.
- Margarita Ricardo: It is visiting day, isn't it?
- Officer Diane Whittlesey: Yes, but your brother's in ad-seg.
- Margarita Ricardo: What's that?
- Officer Diane Whittlesey: It means he's been segregated from the rest of the prisoners. He's had all his privileges taken away, including visitation rights.
- Margarita Ricardo: But I have to see him
- Officer Diane Whittlesey: Sure. Not today.
- Margarita Ricardo: You don't understand...
- Officer Diane Whittlesey: If I had a nickel for every time I didn't understand, you'd be talking to an empty chair.
- Arnold 'Poet' Jackson: [after Seeing White Patches on Skin] DAMN, I might be able to get a cab now.
- [homeboys laugh]
- Augustus Hill: People are defined by three things. Their heads- how they think. Their hearts- what they feel. Their dicks- who they fuck. At the end of the day, each of us has to answer one question. One, not so simple question. Who am I?
- Jason Cramer: You know, all this time in Unit B together, you've never given two shits about me. Now that I'm boxing that Muslim, you're my best pal. Must have been kind of hard deciding who to root for, huh? Let's see, the fag or the nigger? But then again, you know a lot more about what it's like having your cock sucked than having an afro.
- Vern Schillinger: You better watch your mouth, Tinkerbell, or Khan's gonna win by default.