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.
Mr. Monk Goes to the Carnival - S1-E5
Continuity mistake: When Monk is in the review board hearing, in long shots, the wastebasket by the board members' table is empty. When one of the reviewers throws away a paper that misses the basket and lands right next to it, there are several papers already in it. In the next long shot and for the rest of the scene, the basket is empty again and the missed paper is at least two feet away. (00:06:15 - 00:07:40)
Mr. Monk Goes to the Carnival - S1-E5
Continuity mistake: When Kitty runs up to Gitomer, she is not wearing gloves. Later, when Monk gives his summation, careful viewing will show Kitty wearing a glove that's used to hold the knife.
Mr. Monk Goes to the Carnival - S1-E5
Other mistake: Kitty, the killer, is seen running to Gitomer after Lt. Kirk leaves him. She is supposedly running to stab him, but you can see that both of her hands are empty as she dashes to his side.
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