Monk's argument with Sharona about money is interrupted by a routine mugging with an unusual twist — the mugger is renowned computer billionaire Sidney Teal. As everyone tries to get to the bottom of this case, the investigation is dogged by arguments between Monk and his assistant, and questions about a mysterious cop who ran from the scene.
This episode includes examples of the following tropes:
- Benevolent Boss: Sidney Teal is clearly thought of highly by his servants and employees. The chauffeur fixes up Sharona's car, and all he wants from Monk in exchange was to nail Sidney's killer.
- Chekhov's Gunman: Fraidy Cop. While Stottlemeyer is annoyed at being told a cop ran away from the crime scene, Monk realizes that it had to be an impersonator because no cop would run away. So he looks up who rented a cop costume from a nearby shop, which leads him to the actor in question. The actor is able to give full testimony that reveals Modine as a murderer.
- Coincidental Dodge: Monk avoids being shot by a drive-by shooter when he leans down to pick up a handkerchief he dropped, with the bullet zipping by and shattering a glass panel behind him.
- Crazy-Prepared: Sidney was wearing knee and elbow pads under his mugger costume, a detail which alerts Monk that he knew he was going to be knocked down. He also "went the extra mile" and, without telling Archie, hired an actor to play a patrolman who would congratulate Archie for his heroism (and ends up being crucial to proving that Modine was not acting in self-defense).
- A Deadly Affair: Sidney was killed so his wife could have the best of both worlds; her lover and her husband's fortune.
- Dirty Coward:
- Because of the infamous "Fraidy Cop", people are accusing one of Stottlemeyer's officers to be guilty of this. Justified, as "Fraidy Cop" isn't a real cop, but an actor who was paid to pretend to be a cop.
- When the chips are down and their scheme for killing Sidney Teal is exposed, Myra throws Modine under the bus and says it was all his idea.
- Failed a Spot Check: Stottlemeyer addresses "Officer Moratta", not knowing he's the infamous "Fraidy Cop", let alone that he's not even a real cop in the first place.
- Fake Danger Gambit: The motive for the murder. In college, Sidney wanted to impress Angie DeLuca, so he got Modine to help. They conceived a plan in which Modine put on a ski mask, then attempted to "mug" Sidney and his date, and for a moment the mild-mannered Sidney got to look like Superman by fighting the mugger off. Except it came back to bite Sidney later, when Myra began to have an affair with Modine. Modine's way of getting Sidney out of the picture was to contact him and ask him to do the fake mugging attempt scheme again but with the roles reversed, figuring that Sidney would never pass up the opportunity to relive one of the best nights of his life. He was unaware that Modine's plan was to murder him, giving the world the impression that Sidney had had a nervous breakdown, or had discovered Modine's affair with Myra and tried to kill him. What gets Modine caught is that Sidney decided to put a twist of his own on the scheme, and hired an actor named Joseph Moratta to dress as a police officer and commend Modine for his "heroism" after he fought off Sidney. Moratta's testimony exists as evidence of the truth behind what Sidney was really up to.
- Hero with Bad Publicity: The whole SFPD becomes a laughingstock because of the Fraidy Cop debacle. In the end when Fraidy Cop gets exposed to the press again:Stottlemeyer: Shoot him.
Disher: I can't do that, sir.
Stottlemeyer: Then shoot me. - Impersonating an Officer: A police officer is seen running away after seeing Sidney Teal get shot. Turns out it was an actor in a cop costume that Teal had hired as part of a scheme with his killer Archie Modine designed to impress Modine's date.
- Insistent Terminology:Sharona: I can't believe you folded like a cheap suit!
Monk: Tent. For the record, I folded like a cheap tent. - Lonely at the Top: Sidney Teal's chauffeur says that despite having a huge house, incredible riches, and a beautiful wife, Sidney was the loneliest guy in the world. Eventually it's revealed that the reason Modine got him to agree to reverse their "mugging" scheme was because that had been the one moment in his life when he truly felt cool.
- Media Scrum: Stottlemeyer is under pressure to solve the Sidney Teal murder investigation, but it's also burdened by the fact that a uniformed police officer was seen fleeing the scene afterwards. The press latch onto that second subplot, calling him "Fraidy Cop". They harass him so hungrily that he eventually threatens to ban any reporters who ask questions about Fraidy Cop for a year.
- Nice Guy: Willis, Sidney Teal's chauffeur. He fixes Sharona's car for free and implores Monk to find out the truth behind Sidney's death. Willis may also be the only person in Sidney's life who genuinely cared about him given what we learn.
- No Good Deed Goes Unpunished: Sidney returned a favor to a college buddy for helping to create what was his glory days. For his trouble, he's deliberately shot and killed as part of a set up to make it look like Sidney went crazy. All so Modine and Sidney's cheating wife can inherit his money and continue their affair without him. Luckily, Sidney also hired an actor to play a cop and congratulate Modine in front of his date. This unwittingly catches Sidney's killer.
- No Honor Among Thieves: For all her seeming to love Archie, and doing this in order to be with him, Myra is pretty damn quick to try and blame him for the murder plot to save her own neck.
- Noodle Incident: The B-plot is about a theft case Monk just solved and that the client keeps holding off from paying him. With the help of 'Fraidy Cop, Monk and Sharona manage to intimidate the guy into finally paying them.
- Overshadowed by Controversy: In-universe, Stottlemeyer becomes frustrated by the fact that the press are making a bigger deal out of the "Fraidy Cop" issue than of Sidney's death.
- Thrill Seeker: Myra claims that Sidney was always looking for exciting things to do, to the point of comparing him to Batman. However, Monk notices that the photographs on display in the Teal mansion reveal that the most exciting thing he ever did in his life was go to Disneyland.
