Frank: Someone like you doesn't do anything out of the goodness of your heart. It's always transactional.
Jessica: I want to know about Tommy Diehl's death.
Jessica: Drop dead.

Nick: No one would shed a tear if he fell off one of his buildings.
Bobby: Listen to me. You stay away from him! I'll deal with Pat.

When you came in, I thought, maybe there was somebody who put cause above politics. No attachments. No baggage. No debts, but now I know why Bobby brought you in because you're the biggest, baddest operator around.

Derrick

What happened, Nick? Now that Bobby is trying to get his freedom back, McGann showed his hand, didn't he? How bad is it?

Jessica

Jessica: C'mon, Keri. You don't share a bed with someone for five years and not know their secrets.
Keri: Wow.
Jessica: I'm sorry for being so straightforward, but this is important.

You killed Tommy Diehl for McGann, didn't you? Running is not going to solve the problem. Not for you. Not for your brother. I can help you. Let me help you.

Jessica

Bobby: I told you, if you can't pull your weight, I'd go elsewhere.
Pat: Pull my weight? I own you.
Bobby: You don't own shit!
Pat: What did you say to me?
Bobby: You don't own your buildings. You don't own the land they're on. But most importantly, you don't own me.
Pat: You're forgetting a little something.
Bobby: I'm sick and tired of you holding that over my head. You want to drop that bomb and blow yourself up, then be my guest. But for now, get the fuck outta my office, I got a city to run.

Jessica: I'm not having any of that.
Derrick: Any of what?
Jessica: Don't give me that bullshit. I know you two had a dustup on the Ickarus tour.
Derrick: I'm telling you it was nothing.
Jessica: And I'm telling you that whatever it is between the two of you, it needs to end right now.

Jeff: You must be Nick.
Nick: And you are?
Jeff: Jeff Malone. Jessica and I live together.
Nick: How'd you know who I was?
Jeff: Oh, Jessica described you to a tee. Good looking Chicago cop with a striking resemblance to the mayor.
Nick: I'll take good looking.

Pat: Barack, give me and your boss a minute
Bobby: That's not alright!

Jessica: This is your chance to hit the reset button. If you secure campaign funds from other sources, you can finally buy your freedom.
Bobby: It's not that simple. I wouldn't be here without him.
Jessica: What's the point of being here if he controls you? I see how it eats away at you every day. It's time to be your own man. Take away his money, and you take away his power. Unless of course, this is about something else. Is there something else, Mr. Mayor?

Jessica: Who's Tommy Diehl?
Bobby: Ancient history.
Jessica: It didn't feel like ancient history to that man back there.

Pearson Quotes

Bobby: You don't know anything about politics.
Jessica: But I do know about power, and if you sit around waiting for this thing to blow over, you won't have any.

Just stay in your lane. I'm sure she'll stay in hers.

Bobby