Mr. Monk Goes to Group Therapy - S8-E8
Continuity mistake: When Monk and Natalie fall off the bike the bike wheels are on the path. In the next shot they are on grass and the front wheel is at an angle, in the scene where they finish rolling down the hill the bike wheel is now straight.
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