Monk's argument with Sharona about money is interrupted by a routine mugging with an unusual twist — the mugger is Sidney Teal, a man worth billions. 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:
- Chekhov's Gunman: Fraidy Cop. While Stottlemeyer is annoyed at being told a cop ran away from the 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.
- Dirty Coward:
- Because of the infamous "Fraidy Cop", people are accusing that one of Stottlemeyer's officers are 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 Sydney Teal is exposed, Teal's wife throws Modine under the bus and says it was all his idea.
- Engineered Heroics: In college, computer geek Sidney Teal wanted to impress his date Angie DeLuca, so he got his best friend and roommate Archie Modine to help. They conceived a plan in which Modine put on a ski mask, then attempted to "mug" Sidney and his date, so that the mild-mannered Sidney got to look like Superman. Except it came back to bite Sidney later, as his wife Myra began to have a sexual affair with Modine. Modine then decided to remove Sidney from the picture in the best way possible: he met him, reminded Sidney of the prior occasion and convinced him to return the favor, knowing full well that Sidney would never refuse an opportunity to relive one of the best nights of his life. He was unaware that Modine's plan was to shoot him, giving the world the impression Sidney had had a nervous breakdown, or had discovered Modine's affair with Myra and was trying to kill him. It goes one step further: what gets Modine caught is that he didn't know Sidney had gone the extra mile in his planning. Sidney had hired an actor named Joseph Moratta to dress as a police officer, who was to run up and commend Modine for his "heroism" after scaring off Sidney.
- 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.
- Lonely at the Top: Sidney Teal. His chauffeur says that despite having a huge house, incredible riches, and a beautiful wife, Teal was the loneliest guy in the world. Eventually it's revealed that the reason he was performed the mugging that got him shot dead was that he was trying to relive the one moment in his life when he truly felt cool; in college, his friend pretended to mug him and then be scared off so that Teal could impress a date. The same friend went on to have an affair with Teal's wife and to get him out of the way, asked him to stage a fake mugging to impress a girl as an excuse to shoot him.
- 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 (later determined to have been an actor Teal had hired to congratulate Archie Modine had Modine not been planning to shoot Teal) was seen fleeing the scene afterwards. The press latch onto that second subplot, calling him "Fraidy Cop".
- No Good Deed Goes Unpunished: Sidney returned a favor to a college buddy, that was his glory days. He also hired an actor to play a cop and congratulate Modine in front of his date. This unwittingly catches his killer.
- Thrill Seeker: Sidney's widow claims that her husband was always looking for exciting things to do, to the point of comparing him to Batman. However, Monk notices that the photographs in her home don't back up her story.