Monk, Sharona, Stottlemeyer, and Disher arrive in New York City to meet with a witness who has important information on the death of Trudy Monk, when the four suddenly find themselves thrown into a major incident when the Latvian ambassador and his two bodyguards are shot dead in their hotel room. Monk thus finds himself both having to investigate the case, and navigating a city he's distinctly unsuited to.
This episode includes examples of the following tropes:
- Actor Allusion: Monk's stint as a street preacher is reminiscent of Tony Shalhoub's character in Life or Something Like It
- A Deadly Affair: With how Monk determines that Leight is seeing another woman, the episode implies he killed his wife to be with this other woman without a divorce.
- The Big Rotten Apple: Monk finds it difficult enough to operate in San Francisco, so you can only imagine how he finds working in New York, a busier, more densely populated city with a reputation for being far dirtier (figuratively and literally) than San Francisco.
- Brain Bleach: Monk is disgusted by the man who urinated in the subway and points out the further disturbing factor that the guy works in food service (specifically, in a bar).
- Chekhov's Gun: The seemingly useless drawing of an ear which ends up being all that Monk and the sketch artist can produce ends up being a critical clue as to Leight's identity.
- Contrived Coincidence: Monk is only able to solve the crime because, when he's standing in Times Square, he just so happens to look up and notice Steven Leight being interviewed by the cops on the Jumbotron; furthermore, Leight just so happens to be standing in profile enough that Monk can see the side of his head and thus identify him as the killer because of the telltale mole on his ear.
- "Could Have Avoided This!" Plot: As Monk points out during his summation of the case, the Latvian ambassador had actually realized that he was wearing the wrong coat, meaning that Leight could have just asked to swap them and he would probably have done it. Unfortunately, because the ambassador voiced his realization of the switch in his native Latvian instead of English, Leight wasn't aware of this, and jumped straight to murdering him and his bodyguards. On top of that, whereas Mrs. Leight's death was just treated as a mugging and not looked into too closely, the death of an ambassador is naturally treated as a major political incident, which brings the full force of the law down on the case.
- Da Chief: Played with by Captain Cage, who is initially pretty dismissive towards Monk, and hides the fact that Warrick Tennyson is being held by the FBI and on the verge of death from cancer. When Stottlemeyer finds out he gives Cage a What the Hell, Hero? speech and lets him know exactly why Monk needs to speak to Tennyson. Cage apologizes, promises to pull every string he can to get Monk access to Tennyson once the ambassador's murder is solved, and is ultimately as good as his word.
- Disappointed by the Motive: When Warrick Tennyson reveals he was paid to make the car bomb, Stottlemeyer struggles to speak when he hears how little he was paid to do it; a measly $2,000.
- Expospeak Gag: When he partners up with a street preacher, Monk angrily calls Sharona a "fornicator."
- For Want Of A Nail: Monk's both being in New York City to investigate the death of his wife, and insisting on booking one of the city's most prestigious hotels because of its cleanliness rating, puts him in just the right place and time to investigate the murder, which in turn is sparked by a mix-up involving a coat.
- Good is Not Nice: While we've previously seen Monk lose his temper during stressful moments, his actions at the end of the episode are the first hint we get that there's a much darker side to his character.
- I Need a Freaking Drink: Despite having planned out his wife's murder some time in advance, Leight is left shaken enough by actually having done the deed that he needs a drink right afterwards to steady his nerves. In turn, this results in the mix-up that gets the episode's plot underway.
- I Want You to Meet an Old Friend of Mine: Ted Levine (Stottlemeyer) and Mykelti Williamson (Captain Walter Cage) previously played fellow LAPD detectives in Heat.
- Lame Last Words: Subverted. Dimitry Kreslov's final words are apparently "She's now gone meatless," and Monk thinks it's either nonsense or some kind of idiom from his home country. Another Latvian man helpfully offers a translation: Kreslov was actually saying "Sis nav mans metelis," or "This is not my coat." The coat—and the fact that the ambassador was wearing the wrong one—proves the key to the whole case, and it's only because he said so out loud that Monk is able to solve the murder.
- Left Hanging: The whole discussion about which permutation out of Monk, Sharona, Stottlemeyer and Disher are going to have to share one of the three rooms ends up going unresolved, thanks to the four finding themselves smack in the middle of what they assume to be a political assassination.
- Minor Crime Reveals Major Plot: Inverted; a high-profile case about an ambassador and his bodyguards getting massacred is actually committed to hide the killer's murder of his wife.
- Murder Is the Best Solution: As with seemingly all adulterers in the Monk universe, Leight decided that it'd be easier to just kill his wife than either admit his infidelity, or have it exposed. He then jumps straight to murdering the ambassador instead of just asking for his coat back, although this at least can be explained away as panic combined with the influence of alcohol. Now instead of facing the New York justice system for his wife's murder, God only knows what kind of international court is going to come crashing down on his head.
- Overly Long Gag: Monk gets interrupted from saying "I guess I don't really have a choice" by a jackhammer eleven times in rapid succession before he finally shouts over the rattling.
- Race Against the Clock: It turns out that Warrick Tennyson is terminally ill and has three days to live at most; furthermore, he's testifying in a major mob case via deposition and is thus under strict police protection, meaning no one can know where he is. Captain Cage offers to help get around that protection if the ambassador's murder is solved, and the group must solve the case before Tennyson dies and takes what he knows about Trudy's killer to his grave.
- Red Herring: The ambassador's murder wasn't a politically-motivated crime, as everyone initially suspected, but rather the result of a mix-up involving a coat.
- The Reveal: Warrick Tennyson wasn't Trudy Monk's assailant per se, but he did build the bomb that took her life, and reveals that his client was a man with six fingers on one of his hands.
- Revealing Cover-Up: Steven Leight decided to kill Mrs. Leight because he was having an affair and make it look like a mugging gone wrong. While he was getting some alcohol to calm his nerves, his coat (which contained the necklace that the "mugger" took) got mixed up with the ambassador's. In a panic, Leight discarded the possible solution of simply asking for his coat back and opened fire, killing the ambassador and his bodyguards. Of course, the government wanted to know why the ambassador was killed. Due to Monk's investigation of the case, everything comes out, and now he's going to face punishment for three additional high-priority murders too.
- Running Gag: Randy and his watch(es).
- Sanity Slippage: Monk succumbs to this after he's separated from Sharona and taken to the next stop on a subway train. By the time Sharona eventually finds him, he's been recruited to act as a street preacher in Times Square.
- Shell Game: A street hustler was conning some New Yorkers with a playing card version. Monk keeps guessing correctly that the hustler had to bail out of there with Monk's money.
- Shout-Out: The episode's title is a reference to The Muppets Take Manhattan or possibly Friday the 13th Part VIII: Jason Takes Manhattan.
- Skewed Priorities: An incensed Monk really wants to arrest the "urinator" for peeing in public. It takes Sharona to remind him that the urinator's "crime" is nothing when compared to Leight, who murdered four people, including a foreign ambassador, in cold blood.
- Spanner in the Works: Leight almost gets away with killing his wife without incident—except the coat check girl at the bar where he went after the murder inadvertently mixed up his jacket with the Latvian ambassador's, and the pockets contained evidence (the wife's jewelry) that proved his guilt. That leads to Leight killing him and his bodyguards, which in turn ensures that Monk and his team get involved.
- Spotting the Thread:
- Monk notices that the ambassador's coat—and only the ambassador's coat—is soaking wet in the elevator, which proves to be crucial to understanding the crime (the murderer accidentally swapped coats and had to rush over to the hotel in the rain).
- When they confront Leight, Monk points out an unusual purchase that casts doubt on Leight's "grief": he bought anti-snoring medication, which he would not need were he sleeping alone. In the same scene, Leight sarcastically shoves a handful of change in Monk's face, only for Adrian to notice that the mint from Leight's pocket is identical to the one from the bar where the ambassador went before being killed, proving that they were in the same place.
- The Summation: Played for Laughs when, in the middle of explaining how Leight pulled off the crime, Monk goes off-script and starts screaming at a busboy in the bar where the group has gathered, having recognized him as the same man who urinated in the subway earlier. When everyone gets Monk back on track, he hastily rushes through the last part of the summation (to the point where the flashback doesn't even occur) so he can continue focusing on the busboy.
- Suspect Is Hatless: Double Inverted. The only thing Monk could definitely identify about the killer was the shape of his ear, which true to form he remembered to a much more ludicrous detail than the average person would notice...but he still only saw one ear.
- This Is Unforgivable!: Played with. Warrick Tennyson, the man who killed Trudy, begs Monk to forgive him for what he did. Monk's response is to turn off his morphine supply. And then he turns it back on, on Trudy's behalf.
- Toilet Humor: Monk gets an unfortunate view of a man urinating at a subway station in public. It later comes back as a Brick Joke when he recognizes a waiter as the "urinator" during the summation.
- Tranquil Fury: Monk comes face-to-face with the man who made the bomb that killed Trudy. Monk never raises his voice, but it only makes his contempt of the man rather chilling.
- Unwitting Instigator of Doom: The coat girl mixes up the ambassador's coat with Leight's, leading the latter to murder the Latvian ambassador and his two bodyguards.
- Vacation Episode: While not the first example of such, it's the first time an episode's action has taken place in a major U.S. city other than San Francisco. Technically it's also not an actual vacation per se, but Monk and company are hopeful of at least getting to take in a few sights either side of speaking to Tennyson, before the ambassador's murder derails any such plans. Randy, meanwhile, certainly looks like a vacation is what's on his mind throughout.
- What Might Have Been: This episode was originally meant to be a Crossover with Law & Order.
- What You Are in the Dark: Left alone in the same room as the man who killed his wife, Monk is greatly tempted to leave Warrick Tennyson without his morphine supply indefinitely. ...But then he turns it back on, telling him Trudy would've shown him mercy.
