Monk's latest triumph receives a rude interruption when the killer's lawyer, Harrison Powell, shows up, and during the trial, he manages to trip up the defective detective enough to obtain an unjust "not guilty" verdict. Shaken, Monk decides to resign from sleuthing. When Randy asks him to take up a new case to defend his former mentee, a troubled teenager named Rudy Smith, can Monk turn the situation around?
This episode includes examples of the following tropes:
- Amoral Attorney: Harrison Powell, in spades. The man outright bullies Monk into a breakdown in order to get Evan Gildea off, despite the man being guilty as sin.
- Bat Deduction: Powell calls some of Adrian's theories on the Gildea murder out as this.Harrison: Your consultant, Mr. Monk, is he a trained psychologist?
Stottlemeyer: No, no, but he's a lot smarter than any psychologist I've ever met.
Harrison: Well, yeah, he would have to be, having never met my client, to know that my client would not use one of his own statues as a murder weapon.
Stottlemeyer:... That was just a theory. A theory that led us to a substantial amount of other evidence.
Harrison: Okay, we'll get to that "other evidence" a little bit later. I would like to know, if we could just back up for a little bit, how was Mr. Monk able to "divine" where the fight started?
Stottlemeyer: Where the fight started?
Harrison: Where it started. How did he know, for example, that the fight did not start in, say, the foyer?
Stottlemeyer: (in an Oh, Crap! sort of voice) Um... I'll have to consult my notes. - Big Brother Mentor: Randy was assigned to Rudy in the "Big Buddy" program, and takes his arrest very personally, feeling that he failed him somehow. Luckily, he manages to get Monk on the case, and Monk proves that the teen didn't kill the auto shop cashier (though he still ends up with 500 hours community service).
- Backfire on the Witness Stand: Zig-Zagged. Monk serves as a major prosecution witness in Evan Gildea's trial for murdering his wife. Gildea's defense attorney Harrison Powell discredits Monk by revealing his mental disorder, leading him to panic and have a Heroic BSoD, while Gildea is acquitted. Fortunately, Monk finds evidence of Gildea's guilt in a different murder, and this time, Powell can't stop him.
- Black-and-White Insanity: Monk's inability to look at nude sculptures marks the beginning of his downhill slide on the witness stand. Furthermore, Monk must describe the statue that Gildea claims as his alibi, he describes it by squealing through gritted teeth.Stenographer: "Witness: The defendant removed a sheet revealing a naked eeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeee...." [pitch falters]
- Bludgeoned to Death: Both Nancy Gildea and Sarah Paddock were killed the exact same way: A single blow to the medulla oblongata with a blunt object that happened to be nearby.
- Crime After Crime: Evan's murder plot does not go smoothly. He murders his wife, but before he can leave to drive home, he finds out one of his tail lights has burnt out. Knowing his alibi would be ruined if a cop pulled him over for that, he drove to the first auto shop he could find to get a new one. When he gets there, however, juvenile offender Rudy Smith robs the clerk of money in the register and her necklace. To make matters worse, the clerk tells Evan that the thief was caught on the security tapes. Now faced with his alibi being ruined again, Evan whacks her on the head too, steals the tape, and flees after replacing the taillight.
- Defeating the Undefeatable: Powell has never lost a case at the beginning of the episode. By the end, Monk has changed that. One reporter even asks if Powell will change the name of his autobiography.
- Divorce Assets Conflict: The motive behind Nancy Gildea's murder, as she was likely to rook her husband.
- Fake Alibi: Evan's alibi for Nancy's murder was working on a sculpture made from a large chunk of marble that art experts confirm would have taken him over twelve hours to make. The trick is that Evan had made the statue ahead of time, and broke down the block he has a record of receiving down and using it to make gravel in his driveway (in a home out in the woods where the noise doing so would require wouldn't be heard).
- I Never Said It Was Poison: Rudy Smith admits that he robbed an auto parts store and took a necklace and some money from the cashier. How does Monk incriminate Evan Gildea as having then murdered that cashier? Gildea calls Rudy a "dope-smoking, chain-snatching little thug", but Rudy has only told Randy, and not the police or newspapers, about taking the victim's necklace.
- Jerkass Has a Point: Harrison is a slimeball of the highest order, but he makes some valid arguments in his defense of Evan. For example, Stottlemeyer repeats an idea Adrian made in the investigation of how Evan chose to bludgeon Nancy with one of her art pieces instead of his own despite it being closer to where the fight started because he didn't want to damage his own art. Harrison counters that the cops don't know exactly where the fight began, and Monk isn't a psychologist and doesn't really know Evan well enough to determine that he wouldn't use his own art as a murder weapon.
- Justice by Other Legal Means: Evan Gildea gets off for murdering his ex-wife, but is convicted for the clerk he murdered in order to steal an incriminating security tape.
- Karma Houdini:
- Zig-zagged; while Evan Gildea ends up unjustly acquitted for his ex-wife's murder, Monk convicts him for the auto parts store owner he murdered on his way back from the first killing.
- Harrison Powell unfortunately suffers nothing except being dethroned as an undefeatable lawyer.
- Let the Past Burn: Mid-Heroic BSoD, Monk plans to burn his old case files. Naturally, being Monk, he still feels the need to organize them first. However, Randy and Natalie interrupt him.
- Light Is Not Good: Evan arrives at his trial in a bright white suit, and is guilty as sin of two murders.
- Mistaken for Exhibit: A flashback during Monk's testimony shows that at the victim's house, he mistakenly believed a display stand was an art piece.
- Noodle Incident: When DA Friedkin is making sure Monk and his team are truly ready to testify, Natalie remarks that the guys could do this in their sleep. Stottlemeyer follows up that Randy has apparently actually done so. Twice.
- Offscreen Moment of Awesome: We don't get to see how he did it, but despite Powell's silver tongue and ruthlessness, Monk manages to 'defeat' him during the second trial and tarnish his reputation in the process.
- O.O.C. Is Serious Business: Aside from the opening scene, Randy is actually pretty serious because a kid that he used to be a Big Brother Mentor to is under suspicion of robbery and murder.
- Repeat What You Just Said: Evan Gildea has been acquitted of murdering his wife thanks to his defense lawyer discrediting Monk on the witness stand. Afterwards, while working to help clear the name of a friend of Randy's who's been accused of murdering an auto parts store clerk during a snatch-and-grab robbery, Monk finds evidence that the murder was actually committed by Gildea to cover up an emergency taillight replacement he made on his car to preserve the alibi he'd made for his wife's murder. Gildea's lawyer shows up to get him out of custody, and as he's leaving, Stottlemeyer and Monk warn him that the truth will come out.Evan Gildea: When are you people gonna stop hassling me? You've got the real killer here. That dope-smoking, chain-snatching, little thug right over there. [points to Rudy] He killed her. Everybody knows it.
Adrian Monk: Excuse me. Wait a minute. Hey, did you hear what he just said?
Leland Stottlemeyer: Yes, I did. I wonder why you're asking.
Adrian Monk: [to Powell] Did you hear what he just said?
Evan Gildea: I didn't say anything.
Adrian Monk: You just called that young man "a chain-snatching, dope-smoking little thug."
Evan Gildea: I was being kind.
Adrian Monk: How did you know about the chain-snatching? - Shout-Out: Evan's scheme was to use a piece of elaborate art as an alibi to kill his wife, when in reality, the artwork is already completed. One has to wonder if he took inspiration from Max Barsini.
- Smug Snake: Smarmy attorney Harrison Powell has absolutely no qualms about ripping Monk apart on the witness stand, using his phobias and OCD against him, to defend a stone-cold killer. He doesn't lose a bit of sleep over what he does and takes pride in his undefeated case record... which fortunately winds up tarnished by the end when Monk nails Gildea for the murder of an auto store owner.
- So Was X: The D.A. worries Evan Gildea will walk because of his lawyer Harrison Powell:D.A. Charles Friedken: Well, nobody's sleeping today. Harrison Powell is the Prince of Darkness, so be careful up there. Don't volunteer anything. If you don't remember something, just say you don't remember.
Natalie Teeger: But he's guilty, right?
D.A. Charles Friedken: So was O.J. - Spanner in the Works: Rudy robbing the auto store is this for Evan murdering his wife.
- Villain Ball: Gildea was home free and if he hadn't chose to act like a Jerkass and say the incriminating line under I Never Said It Was Poison, he would've gotten away scot free.
- Working the Same Case: Gildea is not only guilty of killing his wife, but also of the murder that Rudy was accused of.
- Worse with Context: One of Rudy's early stunts was graffitiing... police cars.
