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At his small roadside store 'Bennie's Junk ‘n' Stuff', Bennie Wentworth tells his Hispanic assistant Hector Morales to set up booby traps on the property like on any other night. Hector is concerned about the danger, but reluctantly complies.
That night, a mysterious man wearing a suit walks onto the property with a pistol in hand. As he's walking through, a light suddenly clicks on and he bumps into an oil drum, which emits a rattling noise that wakes Bennie up. He warns the man, to not take another step, but the man never listens to Bennie. He hits a trip wire, which pulls the trigger on a shotgun, which shoots him square in the chest and kills him instantly. Bennie comments that nobody listens, and casually lights another cigarette.
The next day, in session with Dr. Kroger, Adrian Monk mentions that he's getting tired of just being a detective. He's not completely satisified by his work. Dr. Kroger suggests to Monk that he pick up a hobby of some sort for when he isn't investigating.
Later, Monk and Natalie Teeger meet Captain Stottlemeyer and Lieutenant Disher at the junkyard. They learn that Bennie is a piece of work, with two tours of duty in Vietnam, and his expertise in booby traps. They also learn about the trip wire that killed the intruder. Monk makes some interesting discoveries about the dead man, noting that he was wearing a suit and Italian shoes. A lack of dust on the man's shoes suggest that he had an accomplice who dropped him off. At that point, Randy panics when he thinks he got in one of Hector's traps, until Stottlemeyer tells him he actually got spider webs on him. However, in the process, Randy also ends up wrecking a bike by denting the wheel, and is eventually persuaded by both Bennie and Stottlemeyer to pay $5 for the bike (the latter mainly to get Bennie to shut up), as the junk shop has the very classic "you break it, you bought it" policy.
Natalie sees a paint set, and she urges Monk to buy it. Bennie makes an offer that Monk can't refuse. Monk has some trouble getting started with his new hobby, so Natalie signs him up for an art class at the local community college. Although his instructor and classmates aren't very impressed with his work, Monk begins to find his stride, painting the world as he wishes it looked, complete with perfectly round clouds and perfectly straight bananas.
Later, Hector Morales returns to the junkyard looking for Bennie Wentworth, and he finds a grisly scene: Bennie is dead, impaled on one of his own booby traps. Monk and Natalie come back to the scene. Randy remarks that it looks like Bennie, who was a little drunk, may have gotten plastered and walked into his own booby trap. Monk notes that something is wrong, and deduces that the knife is 48 inches off the ground, yet the wound on Bennie's body is 54 inches off the ground, a clear six inch discrepancy. He finds the remains of a shattered bottle a few feet away, and concludes that Bennie was killed there, most likely by the accomplice from the first crime, and then moved over to the booby trap to make it look like an accident.
Clearly there was something of value buried amongst the piles of junk - but what could it have possibly been? The answer could lie in Bennie's logbook, in which he kept a record of the items that came in and out of his junkyard. When Monk notices that the last page of the book has been ripped out, Stottlemeyer and Disher set out to find Hector, in the hopes that he might be able to fill in the missing pieces. Disher also claims he can speak Spanish, since they will need an interpreter to talk to Hector, but Stottlemeyer is skeptical.
Back at his apartment, Monk is paid a visit by a man named Petya Lovak, who introduces himself as a Russian art dealer and a passionate admirer of Monk's work. He backs up the claim by buying Monk's two finished paintings on the spot, promising to return soon for Monk's new work, and urging Monk to keep at it. It's advice Monk takes to heart, and soon he has also taken over Natalie's living room in pursuit of his art. Stottlemeyer and Disher are baffled by Monk's work, and shocked that he seems to be blowing off the Bennie Wentworth investigation to work on the paintings. When Lovak shows up and buys two more paintings - and even tries to buy a hideous portrait of Natalie - they grow more bewildered. Is it possible that Monk actually be a good artist? Lovak sure seems to think so. He soon turns up again, this time at the community college's art show. Lovak ignores the work by other artists, but buys more of Monk's paintings – again, all except the portrait of Natalie, which she refuses to sell because it had been a gift from Monk.
Meanwhile, Stottlemeyer and Disher managed to track down Hector Morales at his house, although they have to persuade Hector that they are not INS agents (he and his family are illegal immigrants) and just want his help in retracing the steps of Bennie's last page. He then offers to help.
As Monk is embracing his inner Picasso, Stottlemeyer and Disher finally get a lead on the murders at the junkyard. Hector leads them to a home where he and Bennie had found some canvases and other art supplies sitting on the curb.
Meanwhile, Stottlemeyer and Disher, following Morales' lead, end up near a dumpster, all thanks to Randy's horrible attempts at translating Morales' directions. Stottlemeyer, fed up with these bad translations, decides to have Morales physically lead them to the last stop on their route, leading them to a house. The woman who lives there, Wendy Larson, mentions that her uncle, Scott Larson, recently died. He had taken up painting just a few years ago, apparently, and had also sold his mediocre paintings to a mysterious Russian art collector (she never got the man's name). Stottlemeyer sees a photo of the uncle, and asks Wendy about what her uncle has to do with Carson Paper. She mentions that he worked there for over 30 years. When Randy asks Stottlemeyer why he's so interested, Stottlemeyer explains that Carson Paper has a contract to print currency paper for the U.S. Treasury.
At the art show, Monk begins to have his own suspicions that something is not right. He remembers that when he was loading his paintings into Lovak's van, he saw one unfinished painting inside already. He also remembers that he saw that painting at Bennie Wentworth's junkyard during the investigation of the first death. The day afterwards, when Bennie died, the painting was gone. He realizes it must have been stolen from the junkyard by the first man's accomplice: Petya Lovak. Just then, Stottlemeyer and Disher arrive, asking Monk where Petya is. They explain that they've talked to the Secret Service, and have found that Lovak is working with the Russian mob. The mob has been printing counterfeit money using real currency paper. Scott Larson smuggled paper out of the factory, and disguised the smuggled paper as art canvases to get it through customs. Lovak has been buying up Monk's art because the paper is worth hundreds of thousands of dollars, and Lovak is willing to do anything to get it.
This means trouble for Natalie, who has returned home with her portrait and is once again visited by Lovak. When she continues to hold out Lovak turns violent, threatening her with a knife. As he collars her, Monk gathers the rest of his artwork from Lovak's van, puts it in a pile on the front lawn, and sets it on fire. Lovak, upset, comes rushing outside and is promptly tackled by Stottlemeyer and Disher, who seize him.
Later, Natalie attempts to burn the hideous portrait of herself. Randy stops her, explaining that it's the only painting left and as such is evidence to indict Lovak to the federal authorities, and besides which, it's going to be one of the most famous in the world. Natalie realizes this, and appears to accept this truth, but then she turns around and attempts to burn it again (even screaming for someone to burn the canvas as Randy restrains her).
Stottlemeyer, meanwhile, explains to Monk the rest of the pieces of the investigation. The first victim at the junkyard was one of Petya Lovak's lapdogs. He was trying to steal the canvases. Petya came back the following night, trying again to steal them, during which time he killed Bennie. He was too late, however, as Monk was already painting. He also took the page in the logbook in order to track Monk, and hence the canvases, down. All the money he gave is counterfeit.
With his painting hobby gone, Monk is able to get back to solving crimes, which is what he does best, and Stottlemeyer also suggests that he collect stamps as a hobby.
Why didn't Lovak just buy the canvases from the junkyard? Of course, then there would not have been an episode. . .