Mr. Monk Goes to the Asylum - S1-E6
Plot hole: Monk and Manny go on the roof through Manny's window to grab a piece of cloth. Due to the possibility of suicide, it is highly unlikely that an asylum would have a window that goes directly to the roof, unlocked.
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