Mr. Monk Makes the Playoffs - S7-E13
Other mistake: At the end when Bob Costas is signing off, the mic is in his right hand with the window on his right). When it switches to Natalie watching the upside down TV, the image on the screen is a flipped image (so that the mic is in his left hand and window is on his left). The broadcast wouldn't be a flipped (or mirrored) image than what we see, otherwise, everything the viewer is watching would be backwards (like the writing and numbers).
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