History Recap / MonkS2E16MrMonkGoesToJail

* SympathyForTheDevil: While Dale is, as always, a revolting human being with virtually no redeeming qualities, it's possible to feel a twinge of pity for him when he's denied a window in his jail cell--the one thing he desperately wants. It's telling that Dale [[OOCIsSeriousBusiness drops his jovial facade]] when Stottlemeyer asks about it:

* WhamLine: Dale's revelation to Monk: "The bomb that took your dear Trudy from you...was ''not'' intended for you. It was ''meant for her.''" This completely flips the series's overarching mystery on its head--for two seasons, Monk (and the audience) assumed that [[MurderByMistake he was the target of the explosion that killed Trudy]]. Hearing that Trudy's death was the actual goal forces Monk to start delving into her past to figure out why anyone would want to kill her.

* ArtisticLicenseLaw: Ray Kaspo was slated to donate his organs. In the United States, condemned prisoners cannot be organ/tissue donors. It's possible that since he was a billionaire, Lambert Lawson [[ScrewTheRulesIHaveMoney may have pulled some strings to ensure he got Kaspo's kidneys.

* ArtisticLicenseLaw: Ray Kaspo was slated to donate his organs. In the United States, condemned prisoners cannot be organ/tissue donors.

* MakeAnExampleOfThem: This is is Stottlemeyer's reason behind Dale the Whale's motive for killing Kaspo: while the loan he owed him was trifling, Biederbek could have had him killed as a warning to anyone who might have tried to take advantage of him. Dale immediately shoots the theory down--even in prison, he's still one of the most feared criminals in the world, and ''everyone'' is firmly aware of the power he holds.

* WhamLine: Dale's revelation to Monk: "The bomb that took your dear Trudy from you...was ''not'' intended for you. It was ''meant for her.''" This completely flips the series's overarching mystery on its head--for two seasons, Monk (and the audience) assumed that he was the target of the explosion that killed Trudy. Hearing that Trudy's death was the actual goal forces Monk to start delving into her past to figure out why anyone would want to kill her.

In a few moments, Monk and Sharona travel to the luxurious, fully-furnished jail cell of none other than Dale "the Whale" Biederbeck, the [[FatBastard immensely fat]] criminal mastermind who is imprisoned thanks to the pair's efforts in an earlier case. Dale, in his ingratiatingly charming manner, freely admits that he summoned Monk, as he wants to make a deal with him. An unimpressed Sharona tries to usher Monk out, but Dale wins him back by promising to help him with his own troubles: "One hand washes the other. Now there's a metaphor I ''know'' you can relate to." Biederbeck explains that he has become the prime suspect in Kaspo's murder because of an unpaid debt--$1,200--that the younger man owed the financier. Monk immediately realizes that Dale wouldn't kill someone over what, to him, is pocket change; Dale agrees, but remarks that the cops don't see things that way. Furthermore, his status as a suspect means that he can't have a window installed in his cell wall. Dale proceeds to [[RageBreakingPoint lose his mind with rage]] and tells Monk that he must solve the case for him, because he ''needs'' that window. Monk asks what Dale will give in exchange, and Biederbeck says the magic words: "What you want, Adrian. What you need. ''Information.'' You solve this murder...and I tell you everything I know about ''the man who killed your wife.''"

A while later, Monk, Sharona, Stottlemeyer, and Disher exit the jail. Monk claims that "prison changes a man," and Sharona quips that she certainly wishes that was the case. All seems well...until the final shot of the episode cuts to Dale alone in his cell, watching as a plane headed for New York flies by his window. He wickedly grins to himself: [[SequelHook "Bon voyage, Mr. Monk..."]]

* ArtisticLicenseLaw and ArtisticLicenseMedicine: Ray Kaspo was slated to donate his organs. In the United States, condemned prisoners cannot be organ/tissue donors.

* ADayInTheLimelight: Sharona really gets to shine in this episode. Since Monk is busy going undercover as an inmate, most of the police legwork falls to her, and she's even able to piece together exactly how and why Sylvia killed Kaspo thanks to her training as a nurse. When Monk tries to tell everyone his own findings, Sharona interrupts him: "I know, I already did [[TheSummation the whole summation!"]]

* EvenEvilHasStandards: Spyder Rudner may be a violently destructive prisoner with at least four murders to his name, but even he thinks Neo-Nazis are the worst of the worst and sides with Monk, a cop, over them.

* ANaziByAnyOtherName: Monk ends up having a run-in with the prison's Aryan Brotherhood group, firstly at the midway point of the episode, and then again at the climax.

* NiceJobFixingItVillain: The culprit tried to have Monk killed by convincing him that notorious inmate Spyder is a person of interest in the case. Monk goes undercover as Spyder's cellmate, and the two become friends instead. In the end when Sylvia tries to have Monk killed again (this time with some Neo-Nazi skinheads) Spyder comes to Monk's defense.

While Sharona investigates this new lead, a guard receives a phone call from Warden Christie's secretary, asking Monk to meet him in the prison's Rec Room. Monk heads out...and we discover that the "secretary" was Sylvia, who smiles at the Neo-Nazis standing next to her. She tells them to go take care of Adrian, who ends up hemmed in on all sides by a group of violent skinheads out for his blood. Monk is able to hold them off with a sink's hose and rushes off. Meanwhile, Disher calls Sharona and confirms her theory about Lawson's blood type...AB negative with D antigen. As Sharona hangs up the phone, Warden Christie arrives. They realize that Monk is in serious danger and rush to the Rec Room. Along the way, Sharona, who has solved the case herself, gives TheSummation: the true victim in the crime was not Kaspo, but ''Lawson.'' Kaspo shared Lawson's ultra-rare blood type, which meant that his kidneys were the only ones in the world that could possibly be transplanted into the billionaire's body. Since lethal injections attack the nervous system, the organs would have remained intact if Kaspo had been executed at midnight, so someone created a deadly poison to utterly destroy his kidneys (and the rest of his innards) instead. That someone is none other than Sylvia Fairborn--or, to use her married name, Sylvia ''[=DeMornay=]''. James is her son, and she arranged the murder to keep him from being destroyed in court. Meanwhile, Monk's number is apparently up, as he's surrounded by the Neo-Nazis--only for Spyder to [[BigDamnHeroes appear from nowhere]] and singlehandedly take them all on. His efforts save Monk's life, and the grateful detective promises to put in a good word for Spyder at his parole hearing (in about fifty years).

* ArtisticLicenseLaw and ArtisticLicenseMedicine: Ray Caspo was slated to donate his organs. In the United States, condemned prisoners cannot be organ/tissue donors.

** [[PlayedForLaughs Parodied]] in-universe with Dale the Whale. He's a ruthless, sociopathic, horrible human being, but even ''he'' wouldn't kill someone over something as trivial as $1,2000 ("I wouldn't bend down to pick up twelve hundred dollars--I mean, even if I ''could.''").

A while later, Monk has committed to solving the crime, despite Sharona pointing out that Dale could be lying, especially considering that Monk is the whole reason he was sent to jail in the first place. Monk explains that he can't give up--"This is for Trudy now." The pair's next stop is the kitchen where Kaspo's poisoned last meal was prepared. Warden Christie meets them and explains that Abernathy, who delivered the meal, and all of the cooks have been cleared. But Monk's keen eye notices that one of the cook's time cards was not punched out the previous night. The group investigates and discovers said cook, Tucker--or rather, his corpse--locked in the kitchen freezer. Sharona searches his pockets and discovers a thick wad of cash. Monk now knows that someone paid off Tucker to slip the fatal poison into Kaspo's chili--but who? An answer comes in the form of Sylvia Fairborn, a social worker who serves as the prison's librarian. She tells Monk and Sharona that she overheard Kaspo in a heated argument with another inmate, Darnell "Spyder" Rudner. Kaspo apparently threatened to "tell the world" about a job the two pulled together in Manitoba. It seems like Monk has a new lead, but problems immediately arise: Spyder is the meanest, cruelest, most violent prisoner in the whole compound, with four murders to his name and a history of beating up anyone who touches his stuff. Monk decides that the only thing to do is go undercover as a fellow inmate to try to get information out of Spyder. Sharona and Christie are against the plan, but Monk refuses to give up--"it's for Trudy."

We jump to Spyder being escorted out of solitary confinement, glaring down and frightening men twice his size along the way. He arrives in his cell and meets "Ben Lincoln," who's serving a five-year sentence for embezzling. Things get off to a terrible start, as Spyder immediately notices that Monk has rearranged his belongings and even touched his shiv. He's ready to rip the detective's head off...until Monk reveals that he sharpened the shiv, freshened the tape on the handle, and even relocated it to a better hiding place. That, plus a photo of Trudy on the wall, convinces Spyder that "Ben" isn't all that bad, and the two men begin to become friends. While they talk, Sharona heads to the autopsy room to speak to the medical examiner that studied Kaspo. He reveals that Kaspo's death was [[CruelAndUnusualDeath particularly violent]]--the cocktail of chemicals he ingested liquefied his organs and was enough to kill ''ten'' men. He also mentions that someone's bound to be disappointed, as Kaspo was an organ donor with an extremely rare blood type--whoever was set to receive them is in trouble. Meanwhile, Stottlemeyer and Disher head to Dale's cell to chat with him. He remains unimpressed by their supposed motive, but does admit that he's hired Monk for the case in the hopes of getting his window: "try living without one."

Back in the jail cell, Monk tries to coax information about Kaspo out of Spyder, but the larger man notices that his wristwatch--his most prized possession--has gone missing. Another fight seems imminent, but Monk quickly offers Spyder a deal: he'll track down who stole the watch if Spyder will tell him about Kaspo. Spyder agrees, and the two head for the prison yard, where a gang of Neo-Nazis immediately takes umbrage to Monk's presence. Before they can rearrange his face, though, he suggests that their leader return Spyder's watch--and sure enough, he's wearing it. Spyder is impressed by Monk's detective skills and keeps his word: he's not only never been to Canada, but he didn't even know Kaspo before prison. Monk and Sharona smell a rat and head to the prison library, where Sylvia seems shocked to see Monk alive...perhaps because she was hoping that Spyder would have killed him by now? Their inquiry is interrupted by an inmate complaining about what's playing on TV: an interview with local author James T. [=DeMornay=] whose recent book, ''Richer Than God'', paints a scathing picture of reclusive billionaire Lambert Lawson. Lawson sued [=DeMornay=] for libel and would have completely bankrupted him, but in a lucky turn of events, Lawson recently died of kidney failure, meaning the suit has been thrown out. Sylvia hurries away, but not before Monk and Sharona notice the TV's remote hidden in her purse--she was clearly waiting for that interview.

While Sharona follows up on this new lead, a guard receives a phone call from Warden Christie's secretary, asking Monk to meet him in the prison's rec room. Monk heads out...and we discover that the "secretary" was Sylvia, who smiles at the Neo-Nazis standing next to her. She tells them to go take care of Adrian, who ends up hemmed in on all sides by a group of violent skinheads out for his blood. Monk is able to hold them off with a sink's hose and rushes off. Meanwhile, Disher calls Sharona and confirms Lawson's blood type ("AB negative with D antigen," the rarest in the world). As Sharona hangs up the phone, Warden Christie arrives. They realize that Monk is in serious danger and rush to the Rec Room. Along the way, Sharona, who has solved the case herself, gives TheSummation: the true victim in the crime was not Kaspo, but ''Lawson.'' Kaspo shared Lawson's ultra-rare blood type, which meant that his kidneys were the only ones in the world that could possibly be transplanted into the billionaire's body. Since lethal injections attack the nervous system, the organs would have remained intact if Kaspo had been executed at midnight, so someone created a deadly poison to utterly destroy his kidneys (and the rest of his innards) instead. That someone is none other than Sylvia Fairborn--or, to use her married name, Sylvia ''[=DeMornay=]''. James is her son, and she arranged the murder to keep him from being destroyed in court. Meanwhile, Monk's number is apparently up, as he's surrounded by the Neo-Nazis--only for Spyder to [[BigDamnHeroes appear from nowhere]] and singlehandedly take them all on. His efforts save Monk's life, and the grateful detective promises to put in a good word for Spyder at his parole hearing (in about fifty years).

* BerserkButton: Spyder Rudner, quadruple murderer and most feared inmate in the whole prison, has a famously HairTriggerTemper. But the one thing he hates more than anything is...people touching his stuff. And [[SuperOCD Monk]] ends up in the same cell with him. Everyone immediately assumes that Adrian is dead meat. [[SubvertedTrope Subverted]], though, in that Monk uses his skills to clean the cell, sharpen Spyder's personal shiv, and even put it in a better hiding place. Spyder is genuinely impressed by his skills and lets him off the hook.

* EasilyForgiven: The family of the man Kaspo killed sends him a letter, telling him that they forgive him for murdering their son and are praying for his soul. [[JustifiedTrope Justified]] in that they are a Mennonite family, and that faith calls for a complete lack of revenge or hatred.

* LuxuryPrisonSuite: Dale, largely thanks to his endless cash flow and connections, manages to turn what should have been a life sentence into a rather comfortable stay--he has a carpet, big-screen TV, laptop, books, and access to a Chinese restaurant that delivers.
* MamaBear: Sylvia Fairborn killed Kaspo because her son James wrote a book that criticized billionaire businessman Lambert Lawson. Lawson, who was terminally ill and desperately needed an organ transplant to live, promptly sued James for every penny he had; Sylvia reasoned that if Lawson died, the suit would be thrown out, thus killed the one person who had the same rare blood type as Lawson and thus could have saved his life.

We jump to Spyder being escorted out of solitary confinement, glaring down and frightening men twice his size along the way. He arrives in his cell and meets "Ben Lincoln," who's serving a five-year sentence for embezzling. Things get off to a terrible start, as Spyder immediately notices that Monk has rearranged his belongings and even touched his shiv. He's ready to rip the detective's head off...until Monk reveals that he sharpened the shiv, freshened the tape on the handle, and even relocated it to a better hiding place. That, plus a photo of Trudy on the wall, convinces Spyder that "Ben" isn't all that bad, and the two men begin to become friends. While they talk, Sharona heads to the autopsy room to speak to the medical examiner that studied Kaspo. He reveals that Kaspo's death was [[CruelAndUnusualDeath particularly violent]]--the cocktail of chemicals he ingested liquefied his organs and was enough to kill ''ten'' men. He also mentions that someone's bound to be disappointed, as Kaspo was an organ donor with the extremely rare blood type "AB negative with D antigen"--whoever was set to receive them is in trouble. Meanwhile, Stottlemeyer and Disher head to Dale's cell to chat with him. He remains unimpressed by their supposed motive, but does admit that he's hired Monk for the case in the hopes of getting his window: "try living without one."

While Sharona follows up on this new lead, a guard receives a phone call from Warden Christie's secretary, asking Monk to meet him in the prison's rec room. Monk heads out...and we discover that the "secretary" was Sylvia, who smiles at the Neo-Nazis standing next to her. She tells them to go take care of Adrian, who ends up hemmed in on all sides by a group of violent skinheads out for his blood. Monk is able to hold them off with a sink's hose and rushes off. Meanwhile, Disher calls Sharona and confirms Lawson's blood type...AB negative with D antigen. As Sharona hangs up the phone, Warden Christie arrives. They realize that Monk is in serious danger and rush to the Rec Room. Along the way, Sharona gives TheSummation: the true victim in the crime was not Kaspo, but ''Lawson.'' Kaspo's rare blood type meant that his kidneys were the only ones in the world that could possibly be transplanted into the billionaire's body. Since lethal injections attack the nervous system, the organs would have remained intact, so someone created a deadly poison to utterly destroy Kaspo's kidneys (and the rest of his innards) instead. That someone is none other than Sylvia Fairborn--or, to use her married name, Sylvia ''[=DeMornay=]''. James is her son, and she arranged the murder to keep him from being destroyed in court. Meanwhile, Monk's number is apparently up, as he's surrounded by the Neo-Nazis--only for Spyder to [[BigDamnHeroes appear from nowhere]] and singlehandedly take them all on. His efforts save Monk's life, and the grateful detective promises to put in a good word for Spyder at his parole hearing (in about fifty years).

Back in Dale's prison cell, a window is finally being installed, and Sharona reminds the financier of his promise. After a brief moment of playing dumb, Dale agrees that "a deal's a deal" and begins to talk. His first revelation hits the hardest--Trudy herself was the target of the car bomb that killed her. Monk, who's spent years blaming himself for the murder as he believed that ''he'' was the intended victim, is stunned into silence as Dale mocks him: "I absolve you, Adrian Monk." Biederbeck then coyly replies that he doesn't know why Trudy was targeted, and asks a seemingly unrelated question: "You ever been to New York?" He tells Monk that the man he's looking for--Warrick Tennyson, who was involved in the bombing in some way--will be found there. Sharona announces that if the answers Monk needs are on the East Coast, that's exactly where they'll go.

Back in the jail cell, Monk tries to coax information about Kaspo out of Spyder, but the larger man notices that his wristwatch--his most prized possession--has gone missing. Another fight seems imminent, but Monk quickly offers Spyder a deal: he'll track down who stole the watch if Spyder will tell him about Kaspo. Spyder agrees, and the two head for the prison yard, where a gang of Neo-Nazis immediately takes umbrage to Monk's presence. Before they can rearrange his face, though, he suggests that their leader return Spyder's watch--and sure enough, he's wearing it. Spyder is impressed by Monk's detective skills and keeps his word: he's not only never been to Canada, but he didn't even know Kaspo before prison. Monk and Sharona smell a rat and head to the prison library, where Sylvia seems shocked to see Monk alive...perhaps because she was hoping that Spyder would have killed him by now? Their inquiry is interrupted by an inmate complaining about what's playing on TV: an interview with local author James T. [=DeMornay=] whose recent book, ''Richer Than God'', painted a scathing picture of reclusive billionaire Lambert Lawson. Lawson sued [=DeMornay=] for libel and would have completely bankrupted him--but in a lucky turn of events, Lawson recently died of kidney failure, meaning the suit has been thrown out. Sylvia hurries away, but not before Monk and Sharona notice the TV's remote hidden in her purse--she was clearly waiting for that interview.

While Sharona follows up on this new lead, a guard receives a phone call from Warden Christie's secretary, asking Monk to meet him in the prison's rec room. Monk heads out...and we discover that the "secretary" was Sylvia, who smiles at the Neo-Nazis standing next to her. She tells them to go take care of Adrian, who ends up surrounded on all sides by a group of violent skinheads out for his blood. Monk is able to hold them off with a sink's hose and rushes off. Meanwhile, Disher calls Sharona and confirms Lawson's blood type...AB negative with D antigen. As Sharona hangs up the phone, Warden Christie arrives. They realize that Monk is in serious danger and rush to the Rec Room. Along the way, Sharona gives TheSummation: the true victim in the crime was not Kaspo, but ''Lawson.'' Kaspo's rare blood type meant that his kidneys were the only ones in the world that could possibly be transplanted into the billionaire's body. Since lethal injections attack the nervous system, the organs would have remained intact, so someone created a deadly poison to utterly destroy Kaspo's kidneys (and the rest of his innards) instead. That someone is none other than Sylvia Fairborn--or, to use her married name, Sylvia ''[=DeMornay=]''. James is her son, and she arranged the murder to keep him from being destroyed in court. Meanwhile, Monk's number is apparently up, as he's surrounded by the Neo-Nazis--only for Spyder to [[BigDamnHeroes appear from nowhere]] and singlehandedly take them all on. His efforts save Monk's life, and the grateful detective promises to put in a good word for Spyder at his parole hearing (in about fifty years).

A while later, Monk, Sharona, Stottlemeyer, and Disher exit the prison. Monk claims that "prison changes a man," and Sharona quips that she certainly wishes that was the case. All seems well...until the final shot of the episode cuts to Dale alone in his cell, watching as a plane headed for New York flies by his window. He wickedly grins to himself: [[SequelHook "Bon voyage, Mr. Monk..."]]

While Sharona follows up on this new lead, a guard receives a phone call from Warden Christie's secretary, asking Monk to meet him in the prison's rec room. Monk heads out...and we discover that the "secretary" was Sylvia, who smiles at the Neo-Nazis standing next to her. She tells them to go take care of Adrian, who ends up surrounded on all sides by a group of violent skinheads out for his blood. Monk is able to hold them off with a sink's hose and rushes off. Meanwhile, Disher calls Sharona and confirms Lawson's blood type...AB negative with D antigen. As Sharona hangs up the phone, Warden Christie arrives. They realize that Monk is in serious danger and rush to the Rec Room. Along the way, Sharona gives TheSummation: the true victim in the crime was not Kaspo, but ''Lawson.'' Kaspo's rare blood type meant that his kidneys were the only ones in the world that could possibly be transplanted into the billionaire's body. Since lethal injections attack the nervous system, the organs would have remained intact, so someone created a deadly poison to utterly destroy Kaspo's kidneys (and the rest of his innards) instead. That someone is none other than Sylvia Fairborn--or, to use her married name, Sylvia ''[=DeMornay=.] James is her son, and she arranged the murder to keep him from being destroyed in court. Meanwhile, Monk's number is apparently up, as he's surrounded by the Neo-Nazis--only for Spyder to [[BigDamnHeroes appear from nowhere]] and singlehandedly take them all on. His efforts save Monk's life, and the grateful detective promises to put in a good word for Spyder at his parole hearing (in about fifty years).

When a prisoner is mysteriously poisoned literally minutes before he was sentenced to die by lethal injection, the authorities are ready to pin the blame on Monk's old enemy, Dale "The Whale" Biederbeck, who is serving a life sentence at the same prison. Dale isn't willing to take the blame for this, not least because it'll cause him to miss out on having a new window installed in his cell, and so tempts Monk to try solving the case with the promise of information relating to Trudy Monk's death.

When a prisoner is mysteriously poisoned hours before he was sentenced to die by lethal injection, the authorities are ready to pin the blame on Monk's old enemy, Dale "The Whale" Biederbeck, who is serving a life sentence at the same prison. Dale isn't willing to take the blame for this, not least because it'll cause him to miss out on having a new window installed in his cell, and so tempts Monk to try solving the case with the promise of information relating to Trudy Monk's death.

* AssholeVictim: It's never clear exactly what crimes Ray Kaspo committed in order to get himself the death penalty, but he clearly wasn't a nice person, even if he did have a minor PetTheDog moment with Abernathy prior to his death. Tucker, the chef who fatally poisoned Kaspo himself, also falls under this, as he himself ends up being murdered after doing so.

* KarmaHoudini: Lampshaded by Dale the Whale; he no longer has access to his fortune, and the surroundings and food aren't as nice as before. Regardless, he still has decent amenities, can still eat food to his liking. If anything, he's still as much a prisoner of his own body as he was before he was convicted. The only difference is, there are restrictions to what he can ask for that's outside his prison.
* MyBelovedSmother: It turns out that Sylvia's motive for murdering Kaspo was to indirectly kill a billionaire businessman who had been threatening her son with a lawsuit that would have bankrupted him.

* AssholeVictim: It's never clear exactly what crimes Kaspo committed in order to get himself the death penalty, but he clearly wasn't a nice person, even if he did have a minor PetTheDog moment with Tucker prior to his death. Tucker himself also falls under this, as he himself ends up being murdered, after fatally poisoning Kaspo.

* NoGoodDeedGoesUnpunished: In presumably an attempt to do at least one good thing before he dies, Kaspo gives his drawing pencils to Tucker, to pass on to Tucker's daughter. Not only does Kaspo get fatally poisoned by Tucker right afterward, but Tucker doesn't live long enough to pass the pencils onto his daughter, instead being killed soon afterward because of HeKnowsTooMuch.

* BecauseYouWereNiceToMe: Spyder Rudner at first thinks Monk was touching his stuff and threatens him. But he becomes okay with Monk after seeing how he made his bed, sharpened his knife (and showed a better hiding place for it) and, as a most appreciated gesture, found his stolen watch that his grandfather gave him. This pays off later, as Spyder saves Monk's life and was the one to tip him off that he was most likely being set up.

* BecauseYouWereNiceToMe: Spyder Rudner at first thinks Monk was touching his stuff and threatening him. Monk then explains he sharpened Spyder's knife and shows him a better hiding place for it. This pays off later, as Spyder saves Monk's life.

* DoWrongRight: Monk shows Spyder a better hiding place for his knife, so the guards won't see. Spyder is legitimately impressed.

* NotMeThisTime: The authorities intend to indict Dale the Whale for Kaspo's death, in part because Kaspo owed him $1,200 (which as as much of a motive as they can find for anyone to kill him), and also because he's so hated and guilty of so many other crimes that no jury in the world would fail to convict him, no matter how circumstantial the evidence. Dale notes that normally he wouldn't care seeing how he's going to die behind bars either way, but getting an additional conviction at that particular moment will cause him to [[ArsonMurderAndJaywalking not get a new window installed in his cell]].

** Spyder Rudner is this in-universe, with Sylvia trying to finger him as Kaspo's likely assailant and suggesting that Monk go undercover in the prison population, presumably thinking that someone as obviously unsuited to prison life as Monk will get himself killed or badly hurt in short order.

* NoGoodDeedGoesUnpunished: In presumably an attempt to do at least one good thing before he dies, Kaspo gives his drawing pencils to Tucker, to pass on to Tucker's daughter. Not only does Kaspo get fatally poisoned by Tucker right afterwards, but Tucker doesn't live long enough to pass the pencils onto his daughter, instead being killed soon afterwards because HeKnowsTooMuch.

* PaperThinDisguise: Played with; Monk ''really'' sticks out like a sore thumb when he goes undercover in the prison, but manages to pass himself off as a white collar criminal who ended up with a terrible lawyer, thus causing him to end up in the state penitentiary instead of the kind of minimum security "holiday camp" prison that such criminals usually end up at.

----

* KarmaHoudini: Lampshaded by Dale the Whale; he no longer has access to his fortune, and the surroundings and food aren't quite so nice, but he's still as much a prisoner of his own body as he was before he was convicted.

* ChekhovsGunman: The members of the Aryan Brotherhood whom Monk falls afoul of during his time undercover end up being set up to kill Monk at the episode's climax.

* {{Gonk}}: Dale the Whale looks even ''more'' repugnant than during his debut appearance. Though this isn't meant as a comment on the appearance of replacement actor Creator/TimCurry compared to his original actor Creator/AdamArkin, but rather an understandable consequence of Dale no longer having access to the expensive housekeeping and medical staff he had prior to his incarceration.
* HeKnowsTooMuch: Presumably the reason why Sylvia killed Tucker (or probably more likely, had one of the Aryan Brotherhood members kill him) by locking him in the freezer.

* RedHerring: The authorities and Monk are so busy looking for reasons why people would want to kill Kaspo himself that they fail to realize that Kaspo's murder was actually just a means to an end, namely so that a billionaire businessman would miss out on a liver and kidneys that would have been donated from Kaspo, and pass away himself.

When a prisoner is mysteriously poisoned hours before he was sentenced to die by lethal injection, the authorities are ready to pin the blame on Monk's old enemy, Dale "The Whale" Biederbeck. Dale isn't willing to take the blame for this, not least because it'll cause him to miss out on having a new window installed in his cell, and so tempts Monk to try solving the case with the promise of information relating to Trudy Monk's death.

* HeKnowsTooMuch: Presumably the reason why Sylvia killed Tucker by locking him in the freezer.

* NotMeThisTime: The authorities intend to indict Dale the Whale for Kaspo's death, in part because Kaspo owed him £1,200 (which as as much of a motive as they can find for anyone to kill him), and also because he's so hated and guilty of so many other crimes that no jury in the world would fail to convict him, no matter how circumstantial the evidence. Dale notes that normally he wouldn't care seeing how he's going to die behind bars either way, but getting an additional conviction at that particular moment will cause him to [[ArsonMurderAndJaywalking not get a new window installed in his cell]].
* PaperThinDisguise: Played with; Monk ''really'' sticks out like a sore thumb in the prison, but manages to pass himself off as a white collar criminal who ended up with a terrible lawyer, thus causing him to end up in the state penitentiary instead of the kind of minimum security "holiday camp" prison that such criminals usually end up at.