(At Emily and Taylor's apartment. Taylor has gone to get an address for someone named Mason.)
Wysocki: Out of your league, North Western. She's Harvard material.
Evers: Two girls, their age, living in a place like this? What did she say? They were students?
Wysocki: Oh yeah, she's got a Masters in spending her daddy's money. Same as the rest of these jagholes. Oh, but you wouldn't know anything about that, college boy, would you?

Colvin: Have you ever been down to the wild hundreds after dark?
Mahoney: I try not to make it a habit.
Colvin: Well, let's just say you're a beat copper and you're working a ten-ninety-nine, because budget cuts means that we can't afford to have two officers in a car. And it's three-three thirty in the morning, and as you're riding solo, you hear shots fired. And low and behold, there's a suspect fleeing the scene-
Mahoney: Er, Teresa, I-
Colvin: So, you chase him. Because for forty-five thousand dollars a year, plus overtime, every civilian in this city expects you to chase him. And you know that he's got a gun, and no-one knows where you are, or that you're even in danger. (After reaching inside her desk, she pulls out a radio and places it in front of Mahoney) Now...call for backup. So you can make sure you get home to your kids alive.
(Mahoney reaches for the radio. He tries to turn it on but nothing happens.)
Mahoney: It's dead.
Wysocki: That's right. Because you work a nine hour shift and a lot of these batteries only last for six. So you just got your head shot off because your department, and your mayor, won't give you radios that work.

(Wysocki is pretending to repossess Raymond MacDonald's car when his brother, Marcus, comes running out of the house.)
Wysocki: Just back up, man! We're repossessing it.
Marcus: Repossessing it? Man, I paid cash for this car, homie!
Wysocki: Slow down, so you Raymond MacDonald?
Marcus: Nah, I aint Ray, man! Ray my little brother, man! I'm Marcus. But this aint his car, man!
Wysocki: Well, what about...
Marcus: This is messed up...(To Evers, who is lifting the car up) yo, yo, put my car down, man!
Wysocki: Well, can I talk to your brother? Maybe we can figure this out?
Marcus: Oh, he in the shower, homie! (To Evers) Hey! Put my car down, man!
Wysocki: What about your older brother, Tyrone? Is he in there, too?
Marcus: Yeah, Tyrone in there...How you know about Tyrone?
Wysocki: (Pulls his weapon) The city pays us to know.

Colvin: Detective, you're up early.
Wysocki : No, I'm actually up late. See, I spent half the night trying to figure out how my niece and her partner made a shots-fired call and received absolutely no back-up.
Colvin: What happened?
Wysocki: This radio is what happened. See, Vonda made the call, but the battery was dead; like most of them are, half of the time in this city. Isn't that right?
Colvin: (to her guests) Can I meet all of you upstairs?
Wysocki: I thought you were going to get them replaced.
Colvin: The mayor's office is holding up the request.
Wysocki: Oh, okay. Then I'm going to march up to city hall. I'm going to find our fearless leader. I'm going to shove this radio right where the sun don't shine. Just giving you a heads up just so you know how to play it to the media when the story breaks on the media that a cop put the mayor in Intensive Care with a broken police radio.

Colvin: Look, if shots had been fired on an officer last night, I would have heard about it. So maybe you're just putting a little bit of extra mustard on this particular hotdog.

Wysocki: You know, when you told me you'd never met Emily before, was that with clothes on? Cause I just watched a videotape of you introducing yourself to her in the sack.
Ted Langley II: I'm here with my family praying for a miracle. Have you no decency?
Wysocki: Oh, I have the decency not to be having this conversation in front of your wife.

Evers: (seeing Teddy's father with Emily) That's not Coma Boy. Father Knows Best?
Wysocki: I was thinking more All in the Family.

Judge: Appellate court elections are next month.
Wysocki: Are you ever thinking of retiring?
Judge: They're gonna have to drag my corpse out of that courtroom with the gavel still clutched in my hand.

Evers: You keep secrets from your fiancée. You don't keep secrets from your partner.

Colvin: According to one list, the state of Illinois has produced five of the twenty most powerful women on Earth. What is it about this place that gives us the power and the poise to take the reins? To succeed, to thrive against the odds? If you ask me, it's because if you can hone your craft in the city of Chicago, claw your way up from the corruption and the muck, it gives you the strength to take over the world.

Julie: We sell drinks and a dance floor. I pay my taxes, everything is up to code. So what are you thinking of charging me with, Detective? Felony matchmaking?

Julie: You don't strike me as a prude, detective.
Wysocki: Oh, I'm not a prude, but I am an equal opportunity S.O.B.

Wysocki: You know, I'm about to jump over a big coke supplier and you drag me away for some rich lady, because her kid fried his brain with a wad of smack?
Colvin: Amanda Langley is a major philanthropist and her husband owns half the city.
Wysocki: It doesn't buy any rhythm from where I stand.
Colvin: Which is why you topped out at detective and I'm superintendent.

Wysocki: Chicago's always been a city of big appetites. And while money was first and foremost on the minds of the men who made it, what they chose to spend it on was sex.

Colvin: How long have we known each other, Dennis?
Dennis: Long enough to know that the famous Teresa Colvin charm is about to be unleashed.