When a paperboy ends up dead on his doorstep trying to keep someone from stealing a newspaper, Monk suspects someone wanted to hide something in the news from him.
This episode includes examples of the following tropes:
- All There in the Manual: Only the credits reveal that Vickie's accomplice she later stabs to death is named "Boz Harrelson".
- Asshole Victim: Considering Boz killed Nestor Alvarez and was perfectly fine killing Kevin for his money, Vickie stabbing him to death is pretty deserved.
- Awesome by Analysis: Monk solves two different murders, one of which was in a different country, just by reading a newspaper.
- Black Widow: Vickie is this to Kevin, only dating and marrying him for the winning lottery ticket, and intending to kill him as soon as they "marry".
- Chekhov's Gun: The list of addresses Kevin tells Disher he's lived in before. They're the numbers he uses to play the lottery, which ended up winning and starting the events of this episode.
- Cutting the Electronic Leash: As well as stealing the paper, Vickie tried her best to keep Kevin from getting any calls or watching any TV, for fear he would find out about the lottery ticket and cut her off.
- GPS Evidence: This provides the basis for why the French murderer severed his victim's hands. Both he and the victim, his wife, were curators of the Bastille Prison Museum, and he used an old pair of handcuffs from the collection to bind her while he strangled her to death. However, he lost the key to the cuffs, and it would be ungodly obvious to the police who had killed her if her body was found with them still on.
- Grievous Bottley Harm: Vickie initially tries to use a knife she brought to kill Boz, but he quickly disarms her. As he goes for the knife, she breaks the cream soda bottle she's been drinking from over his head and stabs him with that.
- Innocent Bystander: Nestor's only crime was working with his cousin when someone tires to steal a newspaper.
- Make It Look Like an Accident: Had Monk not realized what Vicky was up to, Kevin would have died in what would likely be considered by the police to be an accident.
- Minor Crime Reveals Major Plot: One story in the newspaper tells how businessman Malcolm Cowley got into two separate car accidents within 10 minutes of each other. Monk finds out the area it happened in was close by to where a grandmother was killed in a hit-and-run, and Malcolm got into those crashes deliberately so he could explain a smashed-in grille.
- Motor Mouth: This episode introduces viewers to Kevin Dorfman, Monk's neighbor upstairs. It establishes quickly Kevin has one of these.
- Red Herring: Monk initially assumes that the killer wanted to hide something in the paper from him, given that the paperboy died trying to stop someone from stealing it. He eventually realizes the killer really wanted to steal Kevin Dorfman's paper, and mistook his front door for Kevin's.
- The Schlub Pub Seduction Deduction: Vickie begins flirting with Kevin and ultimately talks him into marriage after realizing he has a winning lottery ticket. During the summation, Monk says he suspects it must have been easy because of Vickie's attractiveness and Kevin's poor luck with the female sex.
- Single Parents Are Undesirable: Randy Disher subverts the stereotypical issues people have with dating a single parent by placing an ad in the personals clearly referring to Sharona and saying he's okay with kids.
- Speak Now or Forever Hold Your Peace: Monk and Sharona try to stop Vickie from marrying Kevin, only to find they're too late and they've interrupted another, presumably happier, couple.
- Strong Girl, Smart Guy: Deconstructed. Although Monk does pride himself on his intelligence, he's growing insecure about how Sharona is physically stronger than him.
- Til Murder Do Us Part: The victim of the murder in France was killed by her own husband.
- What Does She See in Him?: Vickie is an attractive woman who takes an interest in Monk’s nerdy neighbor Kevin. This turns out to be important since Vickie is only interested in Kevin because he happens to be a lottery winner.
- Ungrateful Bastard: At the end of the episode, Kevin is alive and $43,000,000 richer thanks to his lottery winnings. He gives Monk and Sharona...$400.
- You Have Outlived Your Usefulness: Vickie stabs her accomplice to death so she can keep the lottery money all to herself.
