After listening to Trudy's last message, Monk finally discovers who killed his wife. Racing against time before he dies of poison, he must make a fateful decision.

Monk is called to a murder at the location where he first heard of his wife's murder, and while Monk figures out who the assassin is, he doesn't know that the one who ordered the hit is also responsible for the death of Trudy. Knowing that Monk will eventually put all the pieces together, he orders Monk's death, and when all hope seems lost, Monk discovers something which could finally end his 12-year nightmare.

Monk is summoned to jury duty against his wishes and must solve two crimes: he has to convince the jury the defendent is not guilty, and solve the mystery of a corpse outside the jury room's window.

When Monk's older brother Ambrose calls him about a ""life-or-death matter,"" Monk accepts the call grudgingly and agrees to meet the brother from whom he's been estranged since Ambrose refused to attend Trudy's funeral seven years before. In fact, Ambrose, an agoraphobic packrat whose house is full of bundled up newspapers, has not left the home he and Adrian grew up in for thirty-two years. Believing Ambrose's claim that his next-door neighbor, Pat Van Ranken, has murdered his wife after a loud argument, Monk and Sharona visit Van Ranken and decide to follow him. Van Ranken, meanwhile, is behaving very strangely, entering a potato sack race and a bingo tournament in which the prizes include a cherry pie. It's not hard for the Monk brothers to tie Van Ranken to another murder involving a cherry pie--the challenge is finding a motive for Van Ranken and proving that he did it. The episode provides a glimpse of Monk's family background and the reasons for his estrangement from his brother,

Monk is reunited with his agoraphobic brother, Ambrose, after the murder of an armored car driver.

When Sharona returns to San Francisco to handle legal issues related to an uncle's death, Monk suspects foul play and is torn between the differing styles of Sharona and Natalie.

Monk reluctantly adopts a dog while looking into the suspicious disappearance of its owner.

When monk's favorite singer, Willie Nelson, is suspected of murdering his tour manager, Monk steps in to clear his name.

Monk meets a visiting African widower who's determined to find the hit-and-run-driver who killed his wife near Monk's apartment. Monk begins to identify with the man and confuses his wife with Trudy.

Natalie tries to throw a surprise party for her surprise-hating boss, who is busy trying to solve the murder of a maintenance man.

Upon being reinstated, Monk is put in charge of tracking down a serial killer.

A former San Francisco police detective suffering from an extreme case of obsessive-compulsive disorder is called in to investigate an apparent assassination attempt of a mayoral candidate in which one of his bodyguards is killed.

Monk suspects that the man responsible for the mail bombing murder of rich and beautiful Amanda Babbage is the victim's brother, Brian – who has been in a coma for four months after attempting to lure Stottlemeyer and Disher into a car chase and crashing into two cars. Since the package was postmarked three days before the bombing, Stottlemeyer is naturally skeptical, but he prefers siding with Monk to tagging along behind Agent Grooms of the Bureau of Alcohol, Tobacco, and Firearms, who suspects the victim's other brother, Ricky.

Who would murder a death-row inmate forty-five minutes before his execution--and why? That's the question Captain Stottlemeyer asks Monk--but Monk's response is to ask why it matters. As Monk is hurrying to leave the prison, however, he gets a phone call from his old nemesis, Dale ""the Whale"" Biederbeck, that changes his plans. The police consider Dale a suspect in the inmate's murder (the young man owed him twelve hundred dollars) and refuse to give him a window in his cell until his name is cleared, so Dale strikes a bargain with Monk--solve the case and he'll provide information about Trudy's murder. After interviewing the cook who prepared the dead inmate's last meal, Monk notices that another cook never clocked out the evening before. The missing cook is found dead in a freezer with a wad of bills in his apron pocket--clearly the person who bribed him to poison the inmate was afraid he would talk and killed him, too. On his way out of the prison, he receives another phone call, th

Suffering from amnesia, Monk wakes up believing he is the husband of an eccentric resident of a small town.

As Monk and his friends watch a TV news magazine piece on the solution of his hundredth case, he realizes that one of the victims was murdered by a different killer.

After visiting the set of the hit TV series Crime Lab S.F. during a celebration of its one hundredth episode, Monk suspects the show's star, Brad Terry, of murdering his ex-wife so he won't have to share his huge new paychecks with her. But the actor's alibi seems solid--he was with photographers when the victim's screams were heard. To complicate matters, a fan confesses to the crime and Terry passes a lie detector test. After Terry invites the captain, Disher, and Sharona--but not Monk--to a party, Monk realizes that Terry reminds him of a popular boy who treated him the same way in sixth grade and begins to doubt his own instincts. But when Stottlemeyer invites Monk to hear Marci's confession, Monk's doubts shift to Marci's story. When she tells him that Terry's ex-wife was once an actress who made a single B movie, Monk has the clue he needs to solve the crime.

On her way to film a documentary (apparently about a union dispute), Captain Stottlemeyer's wife, Karen, is badly injured when her car is struck by a tow truck whose nonunion driver has been killed by a sniper. Distraught and furious, the captain blames a sleazy union official and his thug, a theory that seems to be confirmed when a second tow truck driver is murdered. But Lieutenant Disher, in charge of the crime scene investigation, discovers an odd detail that doesn't fit well with this scenario – both the assailant and the murdered truck driver were barefoot. Empathizing with the captain's anguish, Monk offers to do whatever he can to help and of course ends up investigating the case. A small dog that follows Sharona from the crime scene leads her to the home of a handsome man who seems attracted to her, but Monk is more interested in the next-door neighbor's off-kilter sundial. Meanwhile, the captain, fearing that his wife will die, becomes increasingly violent, taking out his anger...

Monk goes undercover as an office worker to solve a case.

Is Monk hallucinating or is he really seeing Trudy?

Needing a date for her brother's rehearsal dinner, Natalie resorts to asking Lt. Disher.

When Captain Stottlemeyer suspects that a suicide is really a murder, Monk confirms his suspicions by discovering that the victim, Joanne Raphelson, was too short to have used the stool she supposedly stood on to hang herself. But the next clue, the remains of an olive, a cherry, and a cocktail onion on a stirring stick, leads Monk to suspect that the murder was committed by an astronaut, Steve Wagner. A little research reveals a motive--Joanne was about to publish a book revealing that Wagner had abused her five years earlier. Now all Monk has to do is to prove that Wagner could commit the murder when he was in outer space.

Monk must match wits against a grandmaster chess player that he suspects of murder.

Monk assumes a dead hitman's identity in order to foil an assassination plot.

After Monk's insurance company refuses to pay for more private therapy sessions, he joins Dr. Bell's therapy group, where it appears that someone is murdering fellow patients.