When Monk's half-brother Jack shows up at his door, he's less than thrilled, especially after learning that Jack has just escaped from prison and is accused of killing a very popular female employee while making his escape.
Monk gets a call from a man who bullied him when he was a kid. He's still affected by it. He's uneasy when he goes to see him. The man wants to hire Monk to follow his wife who he suspects is hiding something from him. Monk accepts to rub his nose in it. And when he follows her he discovers she's hiding something but Monk thinks there's more going on.
Desperate to save the parking lot where Trudy was killed from demolition, Monk enlists the help of a sympathetic councilwoman. But when she goes missing, Monk may be forced to deal with her hapless and incapable assistant.
After Stottlemeyer, Disher and Monk are shredded on the stand in a murder case, causing the accused to go free, Monk loses his confidence. Meanwhile, Disher tries to help a boy he used to mentor who is accused of another murder.
Sharona's big payday is in jeopardy when Monk believes her uncle was murdered, rather than killed by an accidental fall, and the investigation will test everyone's tempers as Natalie and Sharona mark their territories.
In an attempt to woo the lone holdout on the reinstatement committee, Monk accompanies the man's troublesome son and Randy's camping group - where they soon find themselves running afoul of some dangerous armored car robbers.