Charles: He could be in Canada by now. There's so many forests up there. That country is one giant hiding place.

Sergeant Jeffords: So we have good news, and we have bad news.
Charles: My Nana always said, "Bad news first because the good news is probably a lie." Fun fact: she made me cry a lot.

Sergeant Jeffords: Boyle! Were you dreaming about Jake again?
Charles: Why did you wake me up?! I told you never to wake me up!

Charles: Is the equipment secure?
Jake: Check.
Charles: Weapon loaded?
Jake: Check.
Charles: Did you have breakfast?
Jake: What? That's not on the checklist.
Charles: I added it because I care about you.
Jake: No, I did not have breakfast.
Charles: Unacceptable. Look in your pocket.
Jake: Hey, there's little chocolate chips in this.
Charles: Yeah, I'm not an idiot. I know how to trick my best friend into eating his fiber.

Jake: You were behind all this? You played me!
Captain Holt: Like Frans Brüggen plays the flute.

Jake: I've been planning this this theft for three months.
Captain Holt: I know, but I've been planning it for a year. Last Halloween, after you won the bet, I went back to my office to do everyone's paperwork, but I did no paperwork. I started to plot my revenge. I began by creating a word cloud.

Captain Holt: Just to clarify. If you steal my watch by midnight, I will do your paperwork for a week, but if you fail, you will give me five weeks of overtime for free.
Jake: Correct.
Captain Holt: I'm doing a cost/benefit analysis in my head. The benefits outweigh the costs. We have reached an accord.