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A demolition crew is preparing to level a parking garage in downdown San Francisco, to make way for a children's playground. But the workmen call a halt and tell the foreman that some crazy nut has chained himself up to a concrete post inside. The nut is Adrian Monk, who refuses to budge. He explains that his wife, Trudy, was murdered there. When the foreman confronts him, Monk throws the key down a sewer grate. He refuses to let them continue their work. Natalie arrives but doesn't have much luck convincing Monk to give up his cause (at one point, he tries to convince her to chant "We won't go" along with him because otherwise the "we" part wouldn't make any sense).

A city councilwoman, Eileen Hill ( Tamlyn Tomita), pays a visit and tries to convince Monk to leave. He explains that the demolition could destroy possible evidence in Trudy's murder. Touched and impressed by Monk's years of service, Hill agrees to have the city council take a second vote on the matter in four days time, since the vote was 4-3. Monk, relieved, unchains himself.

Cut to three days later. Monk and Natalie are with Captain Stottlemeyer and Lieutenant Disher at the local pier, where two German tourists have been stabbed to death. Monk tries to focus on the case, but the new City Council vote on the garage demolition is happening later that day, and Monk can’t wait to get there. Despite his lack of concentration, Monk notices an interesting clue: one of the victim's camera straps is broken and the camera is missing. He figures that the tourists saw a crime being committed and they took a picture, and the thief must have killed them and taken their camera to eliminate witnesses. He then leaves for the council meeting.

At City Hall, Monk and Natalie run into reporter Paul Crawford ( Tim Conlon), who wants to do a story on Monk's fight to save the garage. He notes that he's glad the parking garage isn't being torn down: parking in that area is a big nightmare.

Outside the council chamber, they run into Monk's nemesis and rival psychiatric patient Harold Krenshaw ( Tim Bagley). Harold offers to vote against the demolition if Monk tells him who his new therapist is. Monk gives an evasive answer, and when Harold (unknowingly) says the correct answer, Natalie accidentally spits water in his face. As they prepare to go in, Disher arrives to tell them that Eileen Hill's sister has filed a missing persons report.

Monk becomes desperate, as the missing councilwoman's vote is the key to saving the garage. Monk and Natalie pay a visit to Eileen Hill's office, and run afoul of Maria Schecter ( Kali Rocha), her pregnant (and very incompetent) secretary. Her incompetence drives Monk to frustration, but they finally convince her to show them Hill's appointment schedule. In it, they discover that her last meeting was with Paul Crawford. Monk, Stottlemeyer and Disher talk to Crawford as he is leaving his car. Crawford has no idea that Hill has disappeared or where she may have gone. Eileen's car has turned up empty and they wonder if she might have been depressed or drinking heavily. Crawford admits that she wasn't as far as he was aware of, and that she wouldn't be drinking now. He tells them that Hill met with him to discuss an article he wrote about contaminated hot dogs, and mentioned how she planned to shut down a local hot dog vendor named George Gionopolis, the self-proclaimed "Hot Dog Czar".

The team goes to a warehouse where Gionopolis and several other hot dog vendors store their vending carts. Monk is disgusted by the filth and the numerous violations of health codes (such as picking up dogs that are dropped on the floor, etc.). Natalie mentions having lost the will to eat from hot dog stands ever again. Disher tries out one of the hot dogs, and when he asks what is in it, the vendor he is talking to says that they use "meat" (because city law states that vendors are required to put the word "meat" in quotes).

Gionopolis claims he hasn't seen Hill in weeks but she had set up an appointment with him on the day she disappeared. However, she never arrived. He admits that he hates her, as she wanted to regulate them very heavily. Monk suggests that Hill did arrive and Gionopolis killed her. Gionopolis denies it and invites them to get a search warrant, saying he wouldn't be stupid enough to hide the body where they could find it.

Later, a desperate Monk puts up "missing" posters for Hill, but can't get one that he puts on a telephone pole straight. Natalie finds him and tells him that Gionopolis has passed a polygraph test and surveillance footage from the warehouse confirms that Hill wasn't at the plant on the day in question.

Monk visits Dr. Bell and asks him to put up a poster, but Dr. Bell suggests that Monk is hanging onto the parking garage for reasons that have nothing to do with evidence. Monk admits that he can't let them tear down the wall that was the last thing Trudy saw. Dr. Bell believes that Monk has recovered enough to let go of the past, but Monk refuses to accept that. Dr. Bell suggests that Eileen Hill got bored with all the council meetings - he notes that he served on the city council in Tulsa, Oklahoma, and when he got bored, he sent his secretary to meetings to cast his proxy vote. This puts an idea in Monk's head.

Monk goes back to Eileen's office and tries to woo Maria Schecter so that she'll cast a proxy vote for Hill against the demolition. They have lunch in the park, buying from a vendor we saw earlier at Gionopolis's warehouse; Monk hesitates to pay for the hot dogs, and tells the vendor "It's a nice 'pleasure' of seeing you again," while making air quotes with his fingers (Monk then promises to not tell Maria's child 20 years later that she ate "hot dogs" during her pregnancy). He also mentions that children don't need a playground - they can use their imaginations and play in the garage. Maria mentions that she got the secretarial job when she saw that Hill had put up a 'Help Wanted' ad at her Lamaze class. She got the job after a very brief interview and a drug test. Maria is reluctant to cast Eileen's vote without ironclad evidence that Eileen planned to vote against the demolition. She mentions that Eileen actually kept a journal: it's at her second apartment, one that no one else, not even the police, knows about.

Monk and Natalie go to the apartment, which obviously appears to have been some sort of love nest. While snooping around, Natalie finds a home pregnancy test that has come up positive. If the councilwoman was having an affair and got pregnant, perhaps her lover is responsible for her disappearance. But with whom was she having the affair?

Unfortunately, Eileen Hill won't be the one to supply answers to the identity of her lover, as her dead body has washed up in the water not far from where the German tourists were found. Stottlemeyer updates Monk on the situation: he notes that Eileen was killed around the same time that the tourists died. She had been strangled with a custom-made British necktie. However, Monk and Natalie are surprised to learn that medical tests have been run and have found that Eileen wasn't pregnant. There’s a lot to sort out, but Monk is more concerned about the latest City Council vote on the garage issue, which is about to take place. They do find Hill's journal in her purse and Adrian gets it to Maria. They find a page in the journal in which the councilwoman writes of her intentions to vote in favor of keeping the garage.

At the council meeting, Harold calls for a brief prayer for Hill and then calls the vote. Maria is sitting in Hill's place and informs them that Monk sent her Hill's journal, and highlighted the part where Hill said she'd vote against the demolition. She casts her vote against and the parking garage is saved.

The council calls a recess and Monk and Natalie run into Maria, Harold, and Paul Crawford in the hallway. A giddy Adrian offers to buy them drinks, but because she’s pregnant and can’t drink alcohol, Maria declines. Monk immediately realizes that Crawford is the secret lover they are looking for: he remembers that when they first talked to Crawford and asked him if Eileen Hill was drinking, he said, "She wouldn't be drinking now." Monk informs Crawford that that was a strange way to answer the question, and now, after Maria’s response to Monk’s invitation, Monk knows why Crawford responded that way: he was under the impression that she was pregnant.

Crawford, who is married, was having an illicit affair with the councilwoman. Monk figures that Eileen tried to persuade Crawford to leave his wife, and she decided to give him an extra "push" by deceiving him into thinking she was pregnant with his child. Carrying out the deception was very simple: she advertised at a Lamaze class. Then she hired Maria Schecter, took her urine under the pretense of a drug test, and used the urine to trigger a positive result on a pregnancy test. Monk insists that this is the only explanation that makes sense, given Maria's spectacular incompetence as an assistant.

After producing the "test", Eileen showed it to Crawford, hoping that it worked, but that's when the plan backfired: instead of leaving his wife, Crawford killed her to conceal the affair, and disposed of the body at the pier. He must have been under the impression that he was alone at the pier when he dumped the body, but then he saw the two German tourists taking pictures. Crawford panicked, and killed them as well - he couldn't take the risk that they had managed to take photographs showing him dumping the body off the pier.

Crawford says that there is no proof, but Monk promptly reaches forward and pulls up his necktie, revealing that Crawford is wearing a custom-made British necktie of the same one that was used as the murder weapon.

Crawford is arrested, but Maria, insulted by Monk's summation and his mention of her incompetence, decides to change her position (supporting the demolition), and Harold gleefully calls for another vote. To add insult to injury, a slip from Natalie has allowed Harold to learn Dr. Bell's name (with Monk having been bragging about him), and he announces that he looks forward to seeing Monk "in the waiting room."

In a repeat of the opening scene, the construction crew is about to demolish the garage, but are forced to wait a few moments while Monk says an emotional farewell to the garage. As Natalie leads him out, they pass a sign declaring the future site of "the Trudy Monk Memorial Playground," indicating that Monk's fight to preserve the memory of Trudy's death wasn't entirely in vain.

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[[Category:Monk episodes]]