Monk gets a visit from Linda Kloster (Elena Evangelo), wife of world chess grandmaster Patrick Kloster (David Strathairn). Linda knows Patrick is planning to kill her and wants Monk to convict him for it after the fact. She gives Monk a check as a sort of retainer.
Monk's so indecisive he can't even respond to Kloster's opening...
However, while Monk knows the culprit, obtaining enough evidence for a conviction may prove more difficult, as Patrick seems to stay one step ahead of him the whole time.
The case is made more difficult by the fact that Linda dies in San Francisco while Patrick is playing chess in Canada. Furthermore, Patrick has Linda's remains cremated promptly, preventing an autopsy.
Linda is Patrick's second wife. His first wife also died under mysterious circumstances. Monk gives Stottlemeyer enough evidence to get a judge to sign off on an exhumation. But the procedure yields nothing.
With help from Natalie's daughter Julie (Emmy Clarke) and a local chess prodigy, Monk gets to play against Patrick in a charity event. Monk suggests that if he beats Patrick, then Patrick will confess. Patrick refuses that wager. Not that Monk could possibly beat him: the poor detective is so wracked with doubt he can't even respond to Patrick's opening move.
This episode contains examples of the following tropes:
- Batman Gambit: Patrick Kloster poisons his wife with a "poison pawn" — a trap that is impossible for the victim to resist. In this case, this involves him discovering her secret stash of liquor, poisoning that, then counting on her to hide the bottle herself so he wouldn't have to.
- Exact Words: When Stottlemeyer realizes that Monk is planning on Framing the Guilty Party, he brings him into a room telling Monk there is something crooked. When Monk states he doesn't see anything crooked in the room, Stottlemeyer replies with "I hope there isn't".
- Framing the Guilty Party: Patrick Kloster has practically admitted to killing his own wife, and the alleged poison matched that which could be extracted from oleander flowers in Patrick's garden. Unable to find adequate evidence and driven to his wits' end, Monk steals some of the flowers, extracts the poison, breaks into Patrick's house to leave it in plain sight on a shelf, and only gets caught when he went back to retrieve the planted vial after his conscience got the better of him, as Patrick had apparently anticipated this very action.
- Freeze-Frame Bonus: When Natalie opens the second of Patrick Kloster's books, you will notice on the left page a list of all of Patrick's other books, which include Ultimate Chess Tactics, The War Of Chess, Winning Endgame Play, Ninja Chess, Unbeatable Chess Strategies, Play Chess and Conquer, Grandmaster Chess Secrets, Five Moves Ahead, and Power Chess Strategy.
- GPS Evidence: Played with. Monk realizes that one of the flowers in Patrick Kloster's yard is poisonous oleander, and takes it to the Captain as his primary evidence... where he is immediately shot down because it's way too common to be admissible as evidence. However, when Monk and Stottlemeyer take a petition to have Patrick's first wife's body exhumed after they realize that her death and Linda Kloster's death are both similar in nature, the judge notes that among other things, Patrick had been growing oleander plants in his garden around the time of his first wife's death as well.
- Graceful Loser: Kloster congratulates Monk for finding proof against him, stating that he plays a brilliant end game. However, this further disgusts Monk, as Kloster treats human lives as mere pieces in a game.
- It's Personal: Although Monk doesn't have a personal connection to Kloster's wife, he can't turn down her pleas to protect her because her desperation reminds him of how Trudy was when she was dying. The rest of the episode revolves around how driven Monk is to put Kloster behind bars when he somehow does kill his wife.
- Lack of Empathy: Patrick feels no grief or guilt about what he did to Linda, seeing the whole incident as a game to flaunt his intelligence. When he continues using chess metaphors after being caught, Monk (who struggles with empathy himself) tells him he's sick of Patrick making light of two womens' deaths.
- Nice Job Fixing It, Villain: Kloster himself tips Monk off on what "Castling" means, which gives Monk his "Eureka!" Moment and allows him to dig up the evidence to convict Patrick.
- O.O.C. Is Serious Business: Randy's goofy mannerisms are entirely absent when the team deals with Kloster. He really—and correctly—doesn't like this guy.
- Reverse Whodunnit: We know that Patrick Kloster is the culprit from the very beginning, due to his wife visiting Monk to inform him right before she herself gets killed. So Monk spends the plot trying to find how to nail Patrick.
- Shut Up, Hannibal!: Once he was finally defeated, Monk tells Kloster off for using chess metaphors for human lives, and Monk further rubs it in by finishing his rant with "Checkmate."
- Smart People Play Chess: Subverted. A big deal is made of how smart Kloster is, since he's an International Chess Grandmaster, but he shows himself to be an arrogant know-it-all who makes mistakes like any other criminal. Monk also gets very tired of his habit of speaking in chess metaphors by the end of the episode.
- The Sociopath: Patrick Kloster repeatedly told Linda he was going to kill her with confidence he wasn’t going to get caught. Upon arriving back home, he pretends to be saddened by her death with Monk and his friends knowing he wasn’t. He constantly makes chess jokes even when Monk figures out why his first wife’s body didn’t test positive on the toxicology examination.
- Tampering with Food and Drink
- Patrick killed Linda by spiking her secret liquor bottle with oleander.
- While Natalie and Monk are staking out Patrick's house, he offers them lemonade. Natalie starts to drink hers, until Monk muses out loud that they could probably nail Patrick if he poisoned Natalie's drink. She immediately spits it out.
- Tantrum Throwing: When Randy tells him Linda Kloster is dead, despite their efforts to save her, Stottlemeyer throws his mug across the room in rage. Randy seems to have anticipated this reaction.
- Villain Ball: Patrick might have saved himself a lot of trouble if he had Monk arrested for trying to frame him. But no, he had to let him free.
- What You Are in the Dark: Monk, desperately wanting to get Kloster, goes as far as Framing the Guilty Party by making the poison and planting it in his house. Just before he leaves the house, he can't go through with it and goes back to retrieve it.
- What the Hell, Hero?: Stottlemeyer gives Monk a stern talking to when the latter reveals he plans to plant evidence to nail Kloster.
