The aftermath of one of Benjy's baseball games is interrupted because of the murder of millionaire executive Lawrence Hammond and his wife Erin. Stottlemeyer thinks Hammond himself was the target, but Monk suspects that the killer really wanted Erin. During the investigation, he meets Scott Gregorio, who was connected to Mrs. Hammond, and following through with this case may just allow the detective to win the game on both the professional and the home front.
This episode contains examples of the following tropes:
- All for Nothing: Walker Browning attempts to assault Scott Gregorio and then kills Mrs. Hammond, all so Gregorio wouldn't break the record and the price on the record-breaking ball Browning caught wouldn't drop...only for all that to go out the window when his dog, Toby, gets ahold of the ball and chews it to a ragged pulp.
- Bait-and-Switch: The scene with Browning looks like it's leading up to a confrontation with his Dobermann, but when he finally tries to sic it on Monk and his friends, it ends up showing no interest in them, instead going for the ball.
- Batter Up!: Walker Browning attacked Scott Gregorio with a baseball bat trying to keep him from breaking the record.
- Beware of Vicious Dog: Browning's dog, Toby, a Doberman, keeps growling and barking throughout the proceedings, and when Monk asks if he's hazardous, his owner answers that he isn't to him. It's eventually subverted as Toby isn't dangerous to humans, just baseballs.
- Bittersweet Ending: Scott Gregorio doesn't break the single-season home run record, but Monk and Sharona solving the mystery of Erin's death gives him solace and helps him put things in perspective. Browning also faces justice on two fronts, being arrested and having his efforts to preserve the value of the ball come to nothing.
- Brick Joke: Early in the episode, Monk and Sharona interview the art teacher who hosted the class that both Erin Hammond and Scott Gregorio took, and he's nude so his students can practice; Monk has a horrible aversion to the public nudity and can barely be in the same room as the guy. At the episode's end, a baseball player removes his towel in the locker room, and Monk recoils again.
- Cannot Tell a Joke: When Monk and Sharona walk into the Hammonds' house, Monk quips that he and Trudy considered buying the same house, which is not likely on a San Francisco cop's salary. Sharona initially asks him if he's serious and then asks if he's feeling okay when she realizes he was joking.
- Close to Home: Monk commiserates with Gregorio since they both lost someone they loved. He decides to solve the case to help the man find closure.
- Cringe Comedy: Monk becoming the replacement umpire is played for awkward comedy up until Benjy comes to bat.
- Crisis Makes Perfect: Benjy fails most attempts at hitting the ball throughout the episode. During the final game (and after some coaching from a professional player), he manages to hit the winning run.
- Determinator: Lawrence Hammond got shot by a bullet, run over by a car, and survived long enough to crawl two and a half miles before somebody found him and called the paramedics, expiring more from gradual blood loss from his injuries than any massive bodily trauma he'd endured. And, as Monk deduces towards the end, it turns out he'd had enough presence of mind to make up a mnemonic phrase to remember the licence plate of the car the killer ran him down with, muttering it to his last breath.
- Disappointed by the Motive: Sharona's tone and phrasing indicate how petty she finds it that Walker Browning was willing to kill two people just so he would be able to sell a baseball.
- Dying Clue: A trucker finds Lawrence Hammond barely clinging to life, and he repeatedly says "Girls can't eat fifteen pizzas" before dying. Monk later determines that the strange phrase was actually a mnemonic device for "GCE 15P," the license plate of the car that the killer used.
- "Eureka!" Moment:
- Monk realizes the meaning of Lawrence Hammond's last words when Gregorio explains the acronym HELP to Benjy, giving Monk the realization that the seemingly nonsensical sentence stood for the killer's license plate number.
- When Stottlemeyer gives the game-winning ball back to Benjy, he advises him to keep it as once he gets to the big time, it'll be worth a lot. This cues Monk in to the motive and culprit.
- Gallows Humor: A spot of this happens when the Hammonds' GPS system directs them to an industrial park, where the hooded killer is waiting with a pistol in hand:GPS System: You have arrived at Skyline Hills Resort.
Lawrence Hammond: The hell I have!
[The shooter steps up to the passenger's side window, and empties a pistol into the car from point blank range]
GPS System: Thank you for using the Safe Voyage System. - Gory Discretion Shot: When the shooter steps up to the car in which the Hammonds are waiting, the moment he opens fire, we cut to an external view of the shooter firing into the car.
- Hypocritical Humor: Stottlemeyer says he can't discuss the baseball game during a homicide investigation...and then gives Randy a complete rundown.
- "I Know What We Can Do" Cut: Scott asks if there's anything he can do for Monk. Monk ponders it a moment...and then the scene cuts to Gregorio coaching Benjy.
- Lame Last Words: Subverted. Mr. Hammond final words were, “girls can’t eat 15 pizzas.” It turns out he was using a mnemonic device to say his killer’s license plate.
- Laser-Guided Karma: Stottlemeyer browbeats the umpire at his son's baseball game, causing the man to quit on the spot. It turns out that the local park manager can have any volunteer umpire who isn't a parent...and he asks Monk. Cue Stottemeyer's expression of This Is Gonna Suck.
- Made of Iron: Lawrence Hammond was not only shot with a bullet, but also run over by a car, and not only didn't expire instantly from all that, but managed to crawl for two and a half miles until somebody found him and called for help, passing on more from blood loss than the extensive injuries he'd endured.
- Morality Chain Beyond the Grave: Discussed. When Gregorio (who still mourns for Erin) wonders how Monk can still do his job without his loved one in his life, Monk tells him that he tries to remain the man his own late wife fell in love with.
- Near-Villain Victory: Browning's actions actually do cause Scott Gregorio to miss out on the record. If not for Monk having worked out his identity, which in turn resulted in Browning's dog getting hold of and eventually destroying the ball, he would have won.
- Nice Job Breaking It, Hero: In the end they lose the baseball because Monk let the dog out of the house. By the time they find the dog, the ball has been mangled into shreds.
- Nice to the Waiter: The housekeeper tells Monk that Lawrence Hammond never forgot the birthdays of his staff or their kids. She actually tears up during the interview about the case.
- Non Sequitur, *Thud*: Subverted; the trucker who discovered Mr. Hammond thought he was talking gibberish, but his last sentence was actually a mnemonic to remember the license number of the car that hit him.
- Overly Long Gag: Monk as umpire insists on cleaning home plate precisely so that not a speck of dust is left on it. Meanwhile, Stottlemeyer asks the kids to get out their homework.
- Public Exposure: Monk and Sharona interrogate a nude model about Mrs. Hammond. Monk is too embarrassed to look at him while Sharona is able to talk to him without a problem.
- Rasputinian Death: Mr. Hammond was shot, run over, and crawled two and a half miles to try to find help...and still lived to give a Dying Clue about his murderer.
- Red Herring: At first it seems like Lawrence Hammond is the murderer's intended victim, especially because the episode opens with reporters hounding him about possible criminal activity for his company. It turns out that Erin Hammond was the actual target, and Lawrence was just a loose end.
- Riddle for the Ages: Was Lawrence Hammond engaging in some shady behavior with his company? Well, we'll never know now...
- Sarcasm-Blind: Monk tries to clean off a smudge on a basketball, unaware that it was an autograph from Michael Jordan. The owner says it's okay; he'll just get Michael to re-sign the ball. Sharona has to tell Monk that he's not serious. Later, the owner sarcastically asks Monk how much money he wants for "cleaning up" and Monk refuses payment. Sharona again tells him "he was joking" and Monk replies "I was joking too".
- Screw the Rules, I Have Connections!: Stottlemeyer's son is thirteen—too old for Little League—but he's still allowed to play thanks to a "special dispensation" that the captain somehow obtained, with Sharona asking "How many parking tickets did you have to fix?" Later, Stottlemeyer tries again by threatening the umpire with a visit from the health inspector...but this time it's subverted, as the umpire declares Screw This, I'm Outta Here and storms off.
- Sheep in Sheep's Clothing: Gregorio is nothing but nice to Monk and Sharona, gives Benjy (his biggest fan) some batting tips, goes to the ball game to see him play, and even helps Monk figure out the Dying Message of one of the victims. However, he is still a person of interest in the case because he was having an affair with the female victim (who Monk firmly believes was the killer's real target). In the end, Gregorio really is innocent of the crime; the culprit killed Erin Hammond to emotionally break Gregorio so he will lose his chance of breaking a record.
- Technology Marches On: Lawrence Hammond has a GPS system in his car, which is used to signify that he's extremely wealthy; furthermore, the device only works using pre-programmed CDs. These days, many classes of car have built-in GPS systems, and they rely on wireless technology for instant updates.
- Tempting Fate:
- In the opening, after Erin Hammond brings up the possibility of criminal charges raised by one of the reporters, her husband tries to reassure her and tells her he'll let her know when she should start being concerned. This is right before both of them are killed by the perp of the week.
- When Dr. Kroger asks Monk about whether he and Trudy ever considered children, Monk says he kept putting it off, convinced they had time. It's obvious that in retrospect he recognizes the irony.
- This Is Gonna Suck: When he realizes that Monk has been made umpire, Stottlemeyer tells the kids to get out their homework because they're in for the long haul.
