Mr. Monk and the Man Who Shot Santa - S6-E10
Plot hole: This episode's entire story line takes place in the six days before Christmas (Dec. 19-24). "Bad Santa" is shot in the right shoulder on the 19th, sustaining a wound serious enough to require wearing a sling for the next several days. Yet at the end, a mere few days later, he's recovered enough to have a knock-down-drag-out fistfight with Monk, wielding a knife and throwing powerhouse punches with his wounded arm as though no injury had ever occurred. (00:38:00)
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