Mr. Monk and the Naked Man - S6-E3
Plot hole: SPOILER Arlene Boras swaps Peter Magneri's MRI scans for those of a healthy person in order to hide the fact that he has a potentially lethal aortic aneurysm. Clearly visible on the MRI scans she is holding are the dates and times of the examination - and the name of the patient. Swapping the records is pointless.
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