During a marathon in San Francisco, a woman, Gwen Zaleski, is thrown from her high-story apartment to the ground, and there is proof that she had been strangled before she even left the building. The number one suspect is a furniture salesman running in the marathon named Trevor McDowell, who claims that he never left the race. Will Monk and Sharona be able to find evidence that proves he did leave the race and murder Gwen?
- Absence of Evidence: The thing that instantly leads Monk to suspect Gwen was murdered is that she was in the midst of painting her toenails, but only got as far as halfway through the eighth one before she was interrupted.Randy: Well, isn't that the style these days?
Sharona: (scoffs) Like you know. - Dark and Troubled Past: Played with. Monk claims an "accident" is what convinced him to forgo his interest in track. It's later Played for Laughs when it turns out the "accident" was more of Monk letting his OCD getting the better of him (He was focused on tying his shoes just right).
- A Deadly Affair: McDowell's reason for killing Gwen. He was her sugar daddy as well as her lover, and she didn't want to let him break it off.
- Fake Alibi: McDowell creates his alibi by putting the chip monitoring his progress in the race on one of the media motorcycles that is filming Tonday's run. He then starts the race and keeps on pace with Tonday and the bike (so that there's footage of him passing through the first few checkpoints) until he reaches a spot on the course where there's no room for spectators. There, he abandons the race, grabs a change of clothes from a bag he stashed there ahead of time, makes his way across town to commit the murder, then rejoins the race near the end. The whole time, the camera bike is taking his chip through the remaining checkpoints and it looks like he was still in the race.
- Hoist by His Own Petard: When he gets busted trying to get rid of the counter that tricked everyone into thinking he completed the race while he murdered Gwen, McDowell pitches the counter into the water and taunts Monk and Sharona over losing their last piece of evidence. The joke ends up being on him, however, because the plastic counter floats and is easily retrieved by the authorities, and he gets arrested.
- Mistaken for Racist: Monk has the bad luck of this happening to him. He shakes hands with many Caucasian people in succession before said-succession ends with the African-American head of security. His promptly wiping his own hands with a hand wipe gives everyone the impression he's prejudiced.
- Pulled from Your Day Off: Stottlemeyer is grumpy about having to oversee the investigation of Gwen's death on what was supposed to be his vacation day. Randy seems to have been yanked from his day off as well, given that he sympathizes with Stottlemeyer and is wearing a Hawaiian shirt rather than a suit.
- Reverse Whodunnit: We see the murder happen at the start of the episode, so we know exactly who the killer is from the start of the episode, it's just a matter of figuring out how Monk will catch him.
- Rousseau Was Right: Sharona suspects that Tonday could be the killer, since the chamomile on the detour to the victim would mask the scent of his chamomile tea. But Monk doesn't believe it on the simple principle that someone as awe-inspiring as his hero couldn't have done it. Although overly trusting, it turns out that Monk's hunch was correct, Tonday didn't kill the girl.
