Mr. Monk is the Best Man - S8-E13
Character mistake: At the end, after Stephanie fired the gun, Captain Stottlemeyer shows her the gun's magazine but calls it a "clip." A police captain like Leland would know the difference between a clip and a magazine and would use the right word.
Mr. Monk is the Best Man - S8-E13
Continuity mistake: When Stephanie leaves Stottlemeyer's office (after he tells her to have TK call him), we see her walk out the door. When the shot changes to Monk, you can see Stephanie in the reflection on the TV walking out of the office again.
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