Captain Holt: Yes, well, I've reached the best part of every vacation: reviewing the charges.

Captain Holt: Peralta, Santiago I'm in your room.
Jake: What? How?
Captain Holt: Patio door was open I pushed through the hedge. Tell me, what is it about me that screams loser?
Jake: Yeah, you know, we're kind of in the middle of gettin' massages right now, sir.
Captain Holt: Oh, how thoughtless of me. I'll get down here so you can see my face.
Jake: Oh, no, that's-
Captain Holt: Hello. The question was, what is it about me that screams loser?

Jake: Okay, you know what? Screw this. You are so smart, and we're gonna prove it to those professors. You're gonna work this case, and you're gonna find those coins.
Captain Holt: Well, I suppose it would be nice to show them I'm more than just a hot, dumb piece of ass.

Captain Holt: Ah, Dean Allister?
Dean Wesley Allister: Policeman Raymond. Good to see you. [chuckles] Read any interesting magazines lately?
Captain Holt: This again? I was waiting for Kevin, I had finished my book, and I happened to glance at an issue of "The Economist" that someone left lying about.
Dean Wesley Allister: All I remember is you becoming unhinged.
[flashback:]
Captain Holt: The only reason I picked it up was to swat a fly. [knocks over a vase] I mean, I'm not crazy. Why are there always flowers here?

Madeline Wuntch: There's John Kelly. Twirl me into him, and I'll place the bug. Hello, John.
John Kelly: Right on time, Madeline. Did Raymond buy it? Did he think you were bonding?
Madeline Wuntch: He was smiling at me like an idiot.
Captain Holt: You've betrayed us, you coffin cave mold beetle!

Sergeant Jeffords: [over radio] Detectives, switch to channel five. Anyone else getting a sense Holt is upset about the new captain coming tomorrow?
Rosa: It's bad. This morning he sighed for the entire length of our elevator ride.
[flashback:]
Captain Holt: [elongated sigh]

Jake: Hey, check it out. Dog bra. Dog bra. Oh, I'm so tired. I can't keep my eyes open. Here, I need you to slap me.
Captain Holt: I'm not gonna do that, Peralta. [slaps Jake]
Jake: Oh!
Captain Holt: I thought perhaps the element of surprise would help.
Jake: It did!

Sergeant Jeffords: Uh, why are you doing that?
Captain Holt: On the other side of your trunk, is the worst person I've ever met. Captain Jeffrey Bouche, the living embodiment of evil.
Jeffrey Bouche: Raymond Holt? As I live and breathe. You have not aged a day. So how's Kevin? How's Cheddar? Come on. Tell me everything.
Captain Holt: Kevin is fine. Cheddar is a dog. He has no concept of good or bad.

Sergeant Jeffords: You're being a little harsh on him, Captain.
Captain Holt: I've been up for promotions against that man on six occasions, and he's prevailed every single time. Why? Because he's a snake.
Sergeant Jeffords: Isn't it possible he gets promotions because he's nice and people like him?
Captain Holt: Please, I hate to say this about anyone, let alone a fellow officer, but that man is full of balogna.
Sergeant Jeffords: Baloney.
Captain Holt: You're right. He's so vile, we should use the crude Americanization of the word. He's full of baloney.

Captain Holt: Hello, deputy chief Wuntch. You've aged.

Madeline Wuntch: Apology accepted. There's a Policeman's Ball tonight. I can plant the bug on Kelly there. And since you don't trust me, you can be my plus one.
Captain Holt: Oh, please. Everyone knows we're enemies. It would raise suspicions.
Madeline Wuntch: Don't worry. I know just what to tell people.
[cut to:]
Captain Holt: Madeline and I are now ... lovers.

Captain Holt: This is what I wanted to show you. Do you know what disappoints me most about this about this picture? That I'm not in it. I can't remember the last time I saw the Nine-Nine so happy. And I wasn't there.
Jake: 'Cause you were working on your presentation to get us a win.
Captain Holt: Yeah, well, it wasn't a real win. I wish I had been in that photo.

Madeline Wuntch: You don't trust me, I don't trust you. The mission is off.
Here's your bug back. It's not an actual bug, so don't eat it, you lizard.
Captain Holt: Ha! You didn't specify the subspecies of lizard. I won that round!

Jake: Look, there's no point in rebranding yourself for the new captain or should I say "craptain" because they're not gonna be here for very long anyways, remember?
Captain Holt: Peralta, stop it. I don't want to hear you bad-mouthing my replacement around the office. Do it surreptitiously. Watch this. I hear that new captain's a pill-popper.
Sergeant Jeffords: They're on their way up.
Captain Holt: Everyone hide your pills.

Captain Holt: You move well. Must be all the extra legs, you crab.
Madeline Wuntch: Don't you find this exhausting?
Captain Holt: Thinking of fresh insults? Not at all, you coffin cave mold beetle.
Madeline Wuntch: I meant our relationship. Aren't you tired of the rivalry? We fight and we fight, and nothing changes. But we're really not so different.
Captain Holt: I suppose we were close once. Remember Brighton Beach?
Madeline Wuntch: 1,200 kilos of heroin in an abandoned subway tunnel. How could I forget?
Captain Holt: The largest drug bust in NYPD history pulled off by a most unlikely duo.
Madeline Wuntch: A woman, and a gay, black detective.
Captain Holt: No, I meant a human and a rotted jack-o'-lantern.
Madeline Wuntch: Don't be so hard on yourself. You weren't all the way rotted back then.