Captain Stottlemeyer: Well, a very good friend of mine has a gambling problem. I need to do an intervention.
Adrian Monk: Maybe Randy could find a support group.
Captain Stottlemeyer: I'm talking about you, Monk.
Adrian Monk: Me? I don't gamble.
Captain Stottlemeyer: Yeah, that's a problem. You should gamble. See, you could be in there right now, gambling, winning his money back.
Natalie: You can't be serious.
Captain Stottlemeyer: Monk, the kid is $35,000 in the hole. That is his savings account, his car payment, and the down payment on his mother's condominium.
Adrian Monk: I can't do it.
Captain Stottlemeyer: Yes, you can. I just saw you.
Natalie: Mr. Monk, don't listen to him.
Captain Stottlemeyer: Look, just... You do that Rain Man thing. Count a few cards. It'll take you an hour-and-a-half.

Adrian Monk: Can I have a different chip? This one's scratched.

Daniel Thorn: I think we can make an exception in Mr. Monk's case. I mean, we're not afraid of him, are we?
Croupier: Nah. You're the boss.
Daniel Thorn: But first, let's make it a little more interesting. Why don't you add two more decks to the shoe?
Croupier: Yes, sir.
Natalie: Mr. Monk, that's 10 decks. That's too many.
Adrian Monk: Bring it.
Daniel Thorn: If you're trying to cheat me, Mr. Monk, we'll catch you. I got friends hiding in the ceiling.
Adrian Monk: Friends in the ceiling?
Daniel Thorn: That's right.
Adrian Monk: I know how you did it. I know how he did it. He murdered his wife.
Man: Good for him. Congratulations. Let's play cards.

Adrian Monk: Stay. Hit me. Here's what happened. You and your wife went out to that fundraiser. She left the penthouse with you, but she never made it downstairs. You killed her in the elevator on the way down. You had less than two minutes, that's all the time you needed. After all, you had help.
Man: Are you going to play or not?
Adrian Monk: Sorry. Hit me.
Daniel Thorn: This man is delusional. He was discharged from the police force six years ago. He's not even a real cop.
Captain Stottlemeyer: Yeah, that's true. But we are. Go on.
Adrian Monk: That wasn't your wife in the lobby. That was Teresa Telenko, your mistress in disguise. Come on, hit me! Stay! Teresa was a trained actress. Is that why you seduced her in the first place, I wonder? I'll split these. Stay. Hit me. Double down. Hit me. You hoisted her up through the access panel. Hit me again. And make it a 10.
Man: Genius!
Adrian Monk: What is that, 17? I'll stay. Hit me. Then Teresa took your wife's place in the elevator. You had 45 seconds. That was plenty of time. Hit me and hit me. Stay. Stay. The elevator door opened, and you two went into your act. $2,000, uptown and down. Let's keep it sassy.
Natalie: Sure you wanna do that? You said you'd quit.
Adrian Monk: Natalie, I know what I'm doing. When the door closed again, Teresa started to scream your name. Whoa. Blackjack. I believe that's the name of the game. Sheryl was already dead when she pressed the glass.
Natalie: That's why her thumbprint was upside down.
Adrian Monk: Wait. I wanna raise my bets. You said it yourself, you have friends hiding in the ceiling. It was a perfect plan. Everybody knew Sheryl was always catching her scarf on something. Nobody was surprised when it happened again.
Daniel Thorn: This is a very interesting fairytale, Mr. Monk, but that's all it is: A fairytale.
Lieutenant Disher: There might be something in the elevator shaft: Blood, hair.
Daniel Thorn: You'd need a court order to even look. Which you're not gonna get, not in this town. So, unless you got something else...
Captain Stottlemeyer: I did, I had it. I had proof, I just can't remember it.
Daniel Thorn: It doesn't matter. You're leaving anyway. This man here is cheating. He's been counting cards. I want him and his friends out of here now.
Adrian Monk: Wait, wait, wait! I'm on fire here. Look, double down!
Daniel Thorn: No, no, no, I told you, Mr. Monk. The house always wins.

Adrian Monk: You said you gambled?
Natalie: I couldn't stop. I was a mess.
Adrian Monk: But you walked away. How did you do it?
Natalie: I had Mitch. How did you do it?
Adrian Monk: I have you.