Mr. Monk Goes to the Carnival - S1-E5
Plot hole: It makes no sense why the police haven't done the most obvious thing and checked for fingerprints on the murder weapon (the knife). It would not only back up the detective's claim that he did not stab the victim (he never touched the knife) but would have given the police a major clue to finding and prosecuting the murderer.
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