Mr. Monk and the Garbage Strike - S5-E2
Factual error: While Monk and Natalie are waiting for the mayor to exit City Hall with his aide, you can see a cable car turning around the corner behind them. San Francisco City Hall is located on Van Ness Avenue between Grove and McAllister Streets, and this is at least six blocks from the nearest cable car line (which would be the turntable at Powell and Market Streets). (00:20:00 - 00:26:05)
Mr. Monk and the Garbage Strike - S5-E2
Factual error: The newspaper with the front page headline about Jimmy Cusack's death comes out the same morning that he is found dead. In reality, since it's said later that the cleaning crew found his body around 7:00 AM, it would be way too late for his death to have appeared in that same morning's edition of the San Francisco Chronicle. It would more likely appear in the next day's paper, by which time Monk had found out that Cusack had been murdered. (00:05:05)
Mr. Monk and the Garbage Strike - S5-E2
Factual error: They said the murder occurred on Monday, April 5th (2006). But that was a Wednesday.
Answer: The two men are trying to work out a secret deal between them without involving the union, which means the workers' interests aren't being represented and defeats the whole purpose of a union. The mayor would lose labor's support and Cusack's union troubles would just be starting.
Captain Defenestrator