The unwilling Monk is pressed by Salvatore Lucarelli, a mob boss, to investigate an apparent gangland shooting. For once, the underworld and the FBI are in agreement; Agent Colmes pressures Monk to take the case so he can get inside information that will enable the FBI to nail the godfather, with a tempting incentive — help getting his badge back.
This episode contains examples of the following tropes:
- All Girls Want Bad Boys: Played with; Sharona is romantically interested in the Godfather's enforcer, Fat Tony, and defends him throughout the episode. Randy explicitly mentions that he thinks it's because she thinks Tony is "dangerous." She keeps dating him even after he tells her that he actually wants to open a bookstore later, despite his suggestion that she might be disappointed in his ambition. However, later, she hears a recording of Tony telling his uncle he said that because it was what she wanted to hear, and she falls out of love with him.
- Caught on Tape: Monk actually does intend to have the FBI catch Phil Bedard's confession on tape, but it backfires because they get static. That's because Monk washes the tie containing the bug in the washing machine due to spilling it with food earlier, and since the bug wasn't waterproof... which is why you never want to bring electronic devices anywhere near water at all unless you are certain they are waterproof.
- Formerly Fat: Sharona has sort of a thing with a mobster called Fat Tony, who's anything but. He was, however, very fat not too long ago, and his nickname of many years has stuck with him. Sharona is bothered by this.
- Insult Backfire: When Stottlemeyer tells Agent Colmes that he isn't good enough to pack Monk's lunch, Agent Colmes agrees, saying that Monk is crazy and there's no way he could pack his lunch.
- Meaningful Echo: Fat Tony gets Sharona's ex-husband, Trevor, to send her the money he's supposed to and only remarks that he can be "persuasive" if he likes. Later, Mr. Bedard confesses, despite his confession not having been recorded. He saw Fat Tony and Vince lurking nearby. Sharona echoes the "persuasive" remark.
- Molotov Cocktail: After talking with a rival gang (Asian in origin) on a tip from a U.S. Mint employee, Monk sits down in exhaustion when he tried to get the gang leader to settle for 100 pushups but failed. Then a molotov cocktail is thrown inside the gym and the gang is forced to evacuate alongside Monk and Sharona. Monk is later blamed by this by the FBI agent in charge of the investigation.
- Never Heard That One Before: Vince gives a couple of different jokes about working at a mint to Mr. Bedard, who, with straight-faced sarcasm, says they're very original.
- Running Gag: Sharona protests the nickname "Fat Tony" several times during the episode.
- Take Our Word for It: Monk is given six options for where to attach the bug during the sting operation. We never get too much description of any of them, but number four is referred to more than once as exceptionally horrible.
- Trouble Entendre: Salvatore Lucelli is cutting up a fish while he tries to hire Monk. At the end of the conversation, after the detective has tried to refuse, he gives him more time to think about it. He also asks Monk which hand is his dominant one and suggests he think about that as well. Monk gets the message.