Mr. Monk and the Very, Very Old Man - S2-E5
Factual error: When Stottlemeyer backs up the video tape at Monk's house, we can hear the sound chattering backwards. Only a huge industrial (studio) machine would do that. Little home VCRs, like Monk's, mute the sound during in-play rewind and fast forward modes. (00:34:30)
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