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tMr. Monk Goes to Jail is the season finale of the second season of Monk.


When a death row inmate is poisoned to death 45 minutes before his execution, Monk is brought in to find out why and runs into his nemesis, Dale the Whale, who will offer Monk information about Trudy if he finds who killed the inmate. The suspects, however, are endless, including the prison librarian, another inmate, and a gang of neo-Nazis.


At 11:15 p.m. at the San Juan Correctional Facility, condemned prisoner Ray Kaspo sits on death row, eating his last meal of ribs and chilli. He is scheduled to be executed at midnight, after a federal court has turned down his last appeal. Kaspo gives a parting gift to his best friend, fellow inmate Abernathy, and tells him to tell their other mates not to worry, he is at peace. But all is not right: Abernathy starts to walk away, but hears Ray choking and gagging, and rushes back just in time to see him collapse to the floor with a violent seizure, with foam streaming from his mouth. Abernathy hollers for help, and guards rush to unlock the cell and try administering aid, but as Warden Christie comes in, it is clear that Kaspo is dead - poisoned. Christie is baffled.

Monk and Sharona are called in to examine the crime scene. He is just as baffled as Stottlemeyer and Disher; Kaspo was a convicted murderer, but the only persons with a strong motive to want him dead were the family of his victim, who have written to say that they forgive him. Moreover, why would someone bother to poison a man 45 minutes before his own execution? Monk, overwhelmed by the prison atmosphere, loses interest in the case and makes his way out, but is stopped by a call at the guard’s station: someone wants to meet with him.

He and Sharona go to visit the prison’s most ostensible inmate: Dale "The Whale" Biederbeck, Monk’s nemesis, who has adjusted to prison life quite easily: he still enjoys the use of his luxurious furniture, a television, an inmate acting as his personal servant, and mountains of specially delivered takeout food. He explains that he is a suspect in Ray Kaspo’s death, since Kaspo owed him $1,200. Both he and Monk know that Dale wouldn’t kill anyone over such a petty sum, but until the killer is caught, the prison is refusing Dale one last privilege: installing a window in his cell wall. Sharona wants to know what on earth could make Monk accept a job from Dale, and Dale offers to share everything he knows about the man who killed Trudy. From then on, Monk is committed.

Monk starts by retracing the steps of Kaspo’s fatal last meal. Warden Christie has already cleared Abernathy as a suspect. Sharona speculates that someone was afraid of Kaspo making some kind of last-minute confession before he died, but Christie discounts that theory, saying that, in his last days, Kaspo, who was sitting on death row for shooting a gas station attendant during an armed robbery, had shared everything he knew and had nothing left to confess.

Monk goes to the prison kitchen and interviews the inmates who prepared the meal, both of whom seem innocent. But Monk notices the timesheets for the kitchen show one inmate, Tucker, didn’t punch out his time card last night. The cook he's talking to last remembers seeing Tucker in the auxilary freezer doing inventory. They unlock the freezer compartment and find Tucker's dead body on the floor. A wad of money is found in his pocket. It is now obvious that someone paid him to poison Kaspo's chili, but not why or by whom, then killed him so he couldn't talk.

While investigating, Monk receives a tip from Sylvia Fairborn, a social worker teaching the inmates to read, that she heard Kaspo talking about a job he pulled in Canada with one of the other inmates, Darnell "Spyder" Rudner.

Monk proposes going undercover as Spyder’s new cellmate. Both Christie and Sharona are against the plan: Rudner, a convicted quadruple murderer, is one of the prison’s most notoriously violent inmates. He is also just finishing a stint in solitary confinement for beating up another prisoner who "touched his stuff." Monk is adamant: "It’s for Trudy."

Spyder comes back to his cell and finds Monk waiting, posing as "Ben Lincoln," a convicted embezzler doing five years. In his obsession with neatness, Monk has certainly touched Spyder’s stuff. Spyder nearly kills Monk within seconds of meeting him, but is taken aback by Monk’s mania for neatness – which has extended to sharpening the blade of Spyder’s concealed shiv, freshening the tape handle, and moving it to what Monk insists is a better hiding place. He is also unexpectedly touched by the photo of Trudy that Monk has taped to his wall. Incredibly, Spyder begins to warm up to his new cellmate.

Sharona interviews the prison’s medical examiner, who says that Ray Kaspo ingested a cocktail of deadly poisons, including mercury, benzedrine, and arsenic, enough poison to kill eight people. These dosages were so strong that Kaspo didn’t simply die - but all of his internal organs were destroyed. Since Kaspo, who had a very rare blood type, was a registered donor and was donating his organs to medicine, the medical examiner comments that someone will be disappointed.

In the cell, Monk drops hints about Rudner’s time with Ray Kaspo, but Spyder pretends not to know what he’s talking about. When he looks at his shelf, he goes berserk when he sees his watch is missing. He nearly kills Monk again, but Monk swears he didn’t take it, and offers Spyder a deal: he’ll find out who did, and in exchange Spyder will tell him what he knows about Kaspo.

The two of them take a walk through the prison yard, and Monk is cornered by a neo-Nazi inmate and two of his cronies. They are about to beat Monk up, but Monk suggests that he return Spyder’s watch first. Spyder is sufficiently feared by the other inmates for the neo-Nazi to comply, and let Monk off. Impressed, Spyder decides to tell Monk the truth. He’s figured out that Monk is undercover, but someone has set him up: he’s never been to Canada in his life, and never met Ray Kaspo before prison.

Monk returns to Sharona and they go to confront Sylvia Fairborn, whom Monk suspects deliberately misled him in the hope that Spyder would kill him. Sylvia sweetly pretends innocence. While they are talking, one of the other inmates complains that he wants to change the channel on the library’s television, but can’t find the remote. On the television is an interview with author James T. DeMornay, who wrote a bestselling biography of reclusive billionaire Lambert Lawson, who died a few days ago from kidney failure. DeMornay admits that Lawson was suing him for libel, but the lawsuit has been thrown out on account of Lawson’s death. As Monk and Sharona start to leave, Sylvia gets up from her seat to help another inmate, and Monk sees the TV remote hidden behind her purse.

Monk and Sharona both start to suspect what happened, and make an inquiry through Randy to confirm their theory. While they are waiting, Sylvia calls, posing as the Warden’s secretary, and asking Monk to meet the Warden in the rec room. Monk goes alone, and finds himself cornered by the neo-Nazis.

Randy calls Sharona, confirming that Lambert Lawson had the world’s rarest blood type. Just then, the Warden comes into the office asking where Monk is. Realizing it was a trap, Sharona and Christie rush toward the rec room.

Here's What HappenedEdit

With her medical background, Sharona has pieced together the case on her own, and gives the summation while they are running to find Monk:

In coming to the prison, the man that Sylvia Fairborn really wanted to kill was Lambert Lawson, who was suing her son James for millions of dollars. Lawson was dying of kidney failure and needed a transplant from Ray Kaspo, the only donor who shared Lawson's ultra-rare blood type. Execution by lethal injection would not ruin Kaspo's kidneys, because the drug used would only destroy his nervous system. Sylvia paid Tucker to spike Kaspo's chili with enough poison to destroy his internal organs. Without the kidneys, Lawson has just died, and Sylvia's son is safe.

Monk is finally cornered in the prison laundry by the neo-Nazis, but Sylvia's original plan has backfired: Spyder appears, telling the Nazis to let his "friend" go. The Nazis attack, and Spyder beats both of them, before Sharona and Christie arrive with security. Monk thanks Spyder for saving his life, but is somewhat disappointed to hear that Sharona has already given the summation.

Monk and Sharona confront Dale in his cell, which now has a window. Dale tells Monk two vital clues: (1) the bomb that killed Trudy was meant for her, not for Monk; and (2) the man who planted it, Warrick Tennyson, can be found in New York City.

Monk emerges from prison, tremendously relieved to be out. But a short while later, Dale watches a plane heading east through his window and chuckles to himself, "Bon voyage, Mr. Monk."

Background Information and NotesEdit

  • There is no San Juan Prison in California; in the later episode "Mr. Monk Is On The Run (Part 2)," Monk says that Dale is incarcerated in San Quentin.
  • Dale the Whale makes his first appearance since Season One's "Mr. Monk Meets Dale the Whale." Tim Curry replaces Adam Arkin.
  • Danny Trejo, who plays Spyder, is an actual ex-convict and reformed gang member.
  • The medical ethics standard in the United States tend to strongly agree on opposing organ donations from excecuted prisoners. Thus a key element of the plot has plausibility issues.
  • His final line in the episode hinted that Dale the Whale had his own sinister motivations for giving Monk the two clues to the circumstances behind Trudy's murder. The motive was later elaborated on in the second part of "Mr. Monk Is On The Run".


  • Dale says he wants a window so he can watch the sunset, so the window would have to face west. But Dale imagines that the plane he sees is Monk’s, which means it would have to be heading east, towards New York. However, it is possible that planes can take off from San Francisco International Airport on a path that would go west of wherever the location of the fictional jail is.
  • California's actual male death row is located at San Quentin State Prison, just north of San Francisco. In this episode, the prison is called San Juan and is apparently located within the San Francisco police jurisdiction.
  • There are a number of unrealistic situations portrayed inside the prison:  1) An inmate scheduled to be executed in less than an hour would not be left so unattended as to require the trustee to yell for help when he went into distress, or to allow the inmate and trustee to exchange objects. 2)  A chronic rule-breaker like Spyder, who had just "put a guy's head through a wall," would not have gotten just one day in solitary confinement with no other loss of privileges. 3) The neo-Nazis would not be allowed to wear swastika lapel pins. 4) Death row inmates are not served their last meal by unescorted fellow prisoners.
  • During the scene where Stottlemeyer and Disher go to see Dale the Whale, Randy is eating a bagel. From shot to shot and point of view to point of view the position and amount of bagel showing, eaten or covered by the napkin changes all the time.
  • How exactly did Spyder find Monk when Monk was being attacked by the nazis? How did he even know Monk needed his help? What was he doing wandering around the prison in the first place?
  • If Tucker never made it back to his cell the night he died in the freezer, why wasn't his empty cell noticed that night?
  • As Ray Kaspo is thrashing on the floor of his cell, a close-up shows a white fluid covering his nostrils and trickling down his upper lip. Immediately after he dies, his upper lip is clear.
  • Sharona is patted down first. Then the guard unsuccessfully tries to pat Monk down. Sharona physically leads Monk back to the guard so he can try again. Since she had physical contact with Monk after her pat down, and before his, Sharona would have been repatted down at this point to make sure there had been no contraband hand-off.
  • I don't believe that prisoners on death row are allowed in the prison population, with access to the library and all.
  • After Sharona explains Monk's obsession with neatness, the cook shares his handshake with Monk, who later shares it with Spyder, but he needs notes to finish it. However, in episode 19, "Mr. Monk Goes to the Theater," he sees the play only once and has it completely memorized.
  • When Sharona and Monk are checking Kaspo's records and Sylvia Fairborn fakes the warden's phone call, the guard says, "You folks are working late," but the establishing shot shows that it's daytime and in the subsequent shots there's lots of sunlight. What kind of prison considers mid-morning or mid-afternoon "late"?
  • It's remotely possible that a four-time murderer like Spyder Rudner might have got some kind of permission slip, but prisons generally do not allow their prisoners to have personal possessions like wristwatches. They're kept in storage and given back when they're let out.
  • Type AB blood is the universal recipient (a person with that blood type can receive a transfusion from any other blood type); type O is the universal donor (a person with that blood type can give blood to anyone but receive it only from another type O).
  • Technically, the episode title should be "Mr. Monk Goes to Prison." Jails, like San Francisco's 850 Bryant, are for short-term confinement, not long-term imprisonment. the San Juan Correctional Facility is (correctly) referred to throughout the episode as a prison, not a jail.
  • Who killed Tucker? Whether it was the real killer, or the neo-Nazis, it doesn't make much sense that they would have left the money in Tucker's pocket.
  • As the guard is patting Monk down for the last time, he begins at Monk's middle before Monk jumps away, but when the camera angle changes for that same shot, the guard is at his legs.
  • The TV in the prison looks too old to be remote-controlled. An inmate mentions that the knobs are broken, but I've never seen a TV with knobs being remote controlled, and there doesn't appear to be a sensor to pick up the remote commands.


Dale "The Whale": I want to make you an offer...
Sharona: Oh please, drop dead!
Dale "The Whale": Well, you'd think I would have by now, wouldn't you? [laughs]

Dale "The Whale": Is that a bagel?

Disher: Mmm-hmm. Want some?
Dale "The Whale": Oh, uh... no, thanks, I can't. I'm on a low-carb diet.

Stottlemeyer: I understand Mr. Kaspo owed you some money.

Dale "The Whale": $1,200. I wouldn't bend down to pick up $1,200. I mean, even if I could. [laughs] Stottlemeyer: No, I think you were trying to make an example of him. That would be more your style.

Dale "The Whale": [laughs] Leland Stottlemeyer is lecturing me about style! The world has gone mad!

Sharona: You promised us some information.

Dale "The Whale": Did I? [laughs for a few seconds, and then gets into a coughing fit] Don't make me laugh. It hurts.

Monk: I’ll tell you guys something. Prison changes a man.
Sharona: Don't you wish?