Mr. Monk and the Three Julies - S6-E13
Plot hole: There is no other reason for Randy to hand Natalie the walkie-talkie but to fill that plot hole. He is in fact in breach of police rules when he hands his department issued radio to a civilian to answer it while he is on duty. The same goes for Stottlemeyer and the car keys he hands to Monk. Even more so since he knows Monk could not even drive that car to the side in the far fetched scenario that a police car had to be moved while the cop is serving a warrant inside the building the car is parked in front of. (00:01:15)
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