Mr. Monk Is Underwater - S7-E5
Character mistake: Commander Whitaker asks what Monk and Natalie are doing on his "ship." No submarine commander would ever refer to his vessel that way. He would refer to it as his "boat."
Mr. Monk and the Genius - S7-E2
Character mistake: At the beginning when Monk is writing Natalie's check, we see a shot of it, but the I in "nine" isn't dotted. As meticulous as he is, Monk would never leave an I undotted (we've even seen him dot someone else's i) especially since it would bother him.
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