Mr. Monk Meets His Dad - S5-E9
Character mistake: At some point Monk asks his father what the device in the car is. His dad tells him it's a GPS. It's difficult to believe that our detective doesn't recognize the machine, even if it's probably another model: the whole plot of the episode 2x03, Mr. Monk Goes to the Ballgame, revolves around a tampered-with GPS.
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