A judge is murdered while placing a 911 call, but before she dies she names her attacker - notorious criminal Dale Biederbeck. The problem is, "Dale the Whale" is over 800 pounds and hasn't left his bed in years.

A police officer and friend of Stottlemeyer is framed for a crime he didn't commit involving a ferris wheel. Meanwhile Monk tries to convince Stottlemeyer to get him reinstated.

When billionaire software magnate Sidney Teal is shot dead by ex-cop Archie Modine after allegedly turning mugger and another policeman mysteriously flees the scene, Stottlemeyer calls in Monk to investigate. Not only is the idea of a billionaire turning mugger hard to swallow, the circumstances of the mugging are suspicious. Why, for example, would a mugger wear knee and elbow pads? Meanwhile, Sharona threatens to quit (this time for sure) when her paycheck bounces, and Stottlemeyer is hounded by reporters demanding information on "Fraidy Cop." Unable to continue the investigation without Sharona's help, Monk returns to the seemingly unsolvable mystery of his wife's murder only to find that his "new" clue isn't new; he's already talked to writer Kelly Street three times. Sharona finds that selling lamps isn't nearly as much fun as working for Monk (with or without money) and comes to the rescue with a new clue involving Teal and Modine.

When Monk's favorite singer, Willie Nelson, is suspected of murdering his tour manager, Monk steps in to clear his name.