Sharona blows into town to deal with the necessary arrangements after her uncle Howie apparently trips and fatally hits his head on a country club golf course. However, Monk quickly finds something suspicious about the circumstances and believes that what was initially dubbed an accident was actually fraud and murder. To make matters worse, Sharona and Natalie quickly begin battling with each other. Can Monk solve the case while dealing with his two bickering assistants?
This episode includes examples of the following tropes:
- A Deadly Affair: Howie Fleming had an affair with Carolyn Walsh, husband to golfer Perry Walsh. Once Perry found out, he manipulated Howie into a scheme that let Perry murder him.
- Both Sides Have a Point: As noted under Gentle Touch Vs. Firm Hand below, both Sharona and Natalie claim that their preferred method of dealing with Monk's neuroses—strongly urging him to face his fears head-on and gently coaxing him to slowly extend himself, respectively—is the best for him. By the episode's end, however, they realize that they are both right: Sharona's Tough Love approach worked immediately after Adrian had his nervous breakdown and needed to get back to a functioning level, and now that he's overcome his initial troubles and can be around people again, Natalie's slower, more patient style is able to help him build up more advanced social skills.
- The Bus Came Back: Sharona returns for a visit.
- Chekhov's Gun: A caddy, one of the witnesses to Mr. Fleming's "accident", complains about his Fujikawa cellphone while being interviewed by Monk.
- Con Man: Howie Fleming, working phony injury lawsuit scams.
- Death by Falling Over: What Howie Fleming's death appears to be at first, that he struck his head on some golf course stairs by tripping on a loose stone. In reality, Howie was fine, and the fall was a con he planned with Perry Walsh...until the two were alone. Then Perry bashed Howie's head against the steps until he was dead.
- Foreshadowing: In Perry's flashback on Howard's death, he said he performed CPR on Howard (i.e. rolling Howard onto his back) but to no avail. However, the photographs of the accident when Sharona is meeting with the country club's legal department clearly show Howard lying face down on the steps, indicating that Walsh isn't being honest.
- Frivolous Lawsuit: Howard had a knack for faking injuries and threatening lawsuits in order to get money from the various settlements.
- Gag Echo: Sharona hopes that the incident was an accident so that she can afford to send Benjy to college. Later in the episode, she falls and breaks her arm, and the first thing she thinks of is about the settlement money.
- Gentle Touch vs. Firm Hand: One of the differences between Sharona and Natalie. Natalie prefers to take a softer approach, which Sharona criticizes as coddling, and Sharona prefers to use tough love on Monk, which Natalie says will traumatize him. Later, after the two of them have calmed down, Natalie says Monk probably needed a firm hand early on and Sharona's work is why she can afford to play Ms. Nice Girl.
- The Ghost: Monk is shown a picture of Benjy and he mentions how much he has grown, but the audience doesn't see it, and Trevor is only mentioned in the fact they are divorced again, with Sharona mentioning that it's permanent this time.
- Golden Mean Fallacy: Intentionally invoked by Monk after he gets fed up listening to Sharona and Natalie debate about whether they should take the elevator up to Walsh's apartment, forcing Monk to confront his claustrophobia, or the stairs. He has them take the elevator up several floors higher than Walsh's, then walk back down to reach his floor.Monk: That way everybody's miserable.
- The Missus and the Ex: Sharona returns to San Francisco to clear up a matter involving her uncle Howie's death and pays Monk a visit, simultaneously meeting Natalie. With their different relationships with the man on full display, Monk spends about half the episode wishing they wouldn't talk to each other, and Captain Stottlemeyer doesn't help things when he warns Monk that they don't mix.
- Nice Job Breaking It, Hero: Sharona insisting doing The Summation in Walsh’s apartment tips the man off. Stottlemeyer is very upset over the whole thing and isn’t sure who to blame.
- Platonic Declaration of Love:
- Stottlemeyer (who hasn't shown interest in either of Monk's assistants) says he loves both Natalie and Sharona.
- Later in the episode, Sharona says that the only reason she managed to put up with Monk was because of love.
- Running Gag: Sharona worrying about paying for Benjy's college education and preferring to consider the incident an accident (so that she can get a settlement) comes up several times during the episode.
- Speak in Unison: Natalie and Sharona start speaking together when listing off Monk's usual lunch order.
- Staged Pedestrian Accident: Monk discovers that Sharona's late uncle Howard Fleming was a con artist: he apparently has had a history of suspicious falls and accidents with monetary compensation settled out of court, and apparently he had been forced into such a lifestyle because he was deep in debt.
- The Summation: Played for Laughs when Sharona impatiently forces herself, Monk, and Natalie into Perry Walsh's closet to give the summation. Unfortunately, Walsh hears every word. Right before Monk can give the summation properly, Sharona tells Monk to quickly explain everything, and Monk does literally just that: he speaks incredibly fast and we are rushed through the summation at triple speed, with Monk being literally unintelligible as a result.
- Tough Love: Sharona confesses to Natalie that she worries she was too hard on her boss. Natalie reassures her that Monk was not in mentally good condition when she started working for him and he needed some pushing.
- Tuckerization: The law firm that initially gives Sharona her settlement for Howie's fall is named for three of the show's writers, Hy Conrad, Salvatore Savo, and Joe Toplyn.
- What the Hell, Hero?: Stottlemeyer was seething about the whole "closet" incident, because Walsh heard everything about The Summation and work things around against them.
- You Never Did That for Me: Natalie is furious to find that Monk paid Sharona more than he does her. Thus, she complains about how Monk hasn't paid her as much. It was a difference of twenty dollars.
