With the duo dry on cases and strapped for cash, Natalie pushes Monk to join the hunt for a missing diamond - one that comes with a $1 million reward. Along the way, they match wits with three other persistent detectives who stalk them constantly, trying to poach their clues, a situation that only gets more tense when the jewel theft escalates to murder.
This episode includes examples of the following tropes:
- 555: Rufus has this on his van. It's one of the things that clues St. Clare in that he is an investigator.
- Berserk Button: Another episode that illustrates that money is Natalie's. Every moment not spent being absolutely obsessed with the prize is spent demanding more consistent payment from the police department. They do ultimately get the latter.
- Bittersweet Ending: Natalie reads the news of Gladys flying to London to collect the reward, but is somewhat assuaged when Stottlemeyer informs her and Monk that the department has agreed to put them on retainer, guaranteeing them a minimum of 16 consultations per year.
- Bounty Hunter: Dirk, one of the three detectives looking for the diamond, is one of these.
- Confess to a Lesser Crime: Warren Landis, a security guard at the museum, gets found out for running a crystal meth lab in his spare time when Monk notices signs of it on him. However, he is still holding onto the diamond at the time, so in order to not be busted with it, he sticks it to the underside of an interrogation room table and later calls "Jennie" to tell her where to find it.
- Doing It for the Art: In-universe with Monk, in regards to detective work. He has absolutely no interest in going after the huge reward, giving a speech about how he uses his gifts for a higher purpose than getting paid, and ultimately only goes for the diamond because Natalie keeps pushing it.
- Flush the Evidence: A woman keeps coming in to confess to comically small crimes (such as stealing a pen from a bank). During one of her "confessions", she admits to getting rid of a body by flushing it. It turns out the "body" was her hamster's.
- Goldfish Poop Gang: The three rival detectives: Inspector St. Claire, a posh Sherlock Holmes Expy; Rufus, a nebbish teenager who relies on gadgets; and Dirk, a burly biker/Bounty Hunter with an anger problem. Each gets in Monk's way in their own, individual means, and keep showing up after they decide to work together.
- Hoist by His Own Petard:
- A rare example of it happening to the hero. Monk continually harasses Gladys for not cleaning the undersides of tables and desks, which comes back to bite him in a big way when she finds the diamond—stuck to the underside of a table.
- Dirk traps Monk, Natalie, Stottlemeyer, Disher, and the other two investigators in a room with him by breaking the key in the lock. This prevents any of them from getting to the diamond before Gladys finds it. What's more, Disher arrests him because he's just committed six counts of unlawful imprisonment, two of them involving police officers.
- Informed Ability: Those three detectives really didn't show much of their actual detective skills and instead spent the entire episode hounding Monk and Natalie.
- Downplayed with St. Clare. When the trio lose Monk and Natalie on their footchase, they try to think like Monk. While Dirk and Rufus just walk around mimicking Monk's physical thought processing dance thing, St. Clare notices someone putting fliers on car windshields and figures out which way Monk and Natalie went by seeing where they've all been straightened.
- Innocently Insensitive: Natalie is relieved to learn that the department has agreed to put Monk on retainer, with a guaranteed 16 homicide consultations each year; Monk responds, "what about after that?" as if he's hoping that more than 16 people get killed in unsolvable ways each year (of course, San Francisco is a major city, so that may not be insensitive as much as realistic).
- Inside Job: Monk figures out the museum robbery was this, as the thieves opened a display case with a mace in it to break the glass on the diamond's case. He later realizes that one of the security guards was the inside man.
- Ironic Echo: "Ka-CHING!"
- Leaning on the Fourth Wall: While they miss out on the titular big reward, Stottlemeyer gives them a consolation in the end: Monk has been put on retainer with a guaranteed sixteen cases a year for two years, after which point "who knows?" To make the gag clearer: every season of the series except the first has sixteen episodes - it's a in-universe nod to the fact that the show had been renewed for two more seasons.
- Line-of-Sight Alias: After killing Chasen at the meditation center, Landis' girlfriend/accomplice sees the name of Jennie Mandeville on a memorial plaque and decides to use it as her own. The real Jennie, who founded the center, had died 28 years earlier.
- Never Learned to Read: The bounty hunter, Dirk, proves to be illiterate, being unable to read the name of an ID card when he and the other two detectives are investigating the robbery, as well as not being able to tell that a door says "Push".
- Nice Job Breaking It, Hero: Played for Laughs. Because of Monk repeatedly pestering Gladys the cleaning lady to clean the underside of the tables and desks, she does so in the interrogation room and finds the diamond. Likewise, Dirk locks himself and the other three detectives in a room as a way of convincing Monk that they can split the reward four ways, and thus ensures that none of them can stop Gladys from finding the diamond herself.
- No Honor Among Thieves: Danny Chasen was killed so "Jennie" could keep the loot for herself (and possibly her boyfriend, the security guard).
- No Name Given: We never learn "Jennie Mandeville's" real name.
- Noodle Incident: It's never explained why Gladys the cleaning lady had to get a restraining order against Monk (presumably, it has something do with his insistence she clean under that tables. That, or we don't want to know...).
- "Shaggy Dog" Story: Monk and Natalie miss their chance at the diamond despite it being right in front of them, but they do manage to solve the case, and Stottlemeyer is able to arrange for the SFPD to keep them on retainer for at least two years.
- Stalker without a Crush: The three men who are after the missing diamond follow Monk and Natalie just to get some extra information on the diamond’s location. The youngest man, Rufus, follows and records Monk while he’s in a session with Dr. Kroger.
- Tampering with Food and Drink: "Jennie Mandeville" poisons Danny Chasen's tea so that she and her boyfriend can keep for themselves any money they get from selling the diamond or claiming the reward.
- Technologically Advanced Foe: Rufus, who uses a range of high-tech gadgets, tries to be this to Monk but doesn't have much success. He slips a tracking device into Monk's pocket but is quickly found out, then tries to use a voice stress analyzer on the tai-chi session leader (who doesn't speak), and finally gets caught eavesdropping on a session between Monk and Dr. Kroger.
- Tuckerization: "Jennie Mandeville" or whatever her real name is gets her alias from Mandeville Productions, the studio that produced the series.
