Mr. Monk Goes to Jail - S2-E16
Continuity mistake: When Stottlemeyer and Disher are interviewing Dale the Whale in the bed, in the scene where the fat guy says "Is that a bagel?", Disher's bagel keeps changing size as the camera angle switches, getting bigger and smaller.
Mr. Monk Goes to Jail - S2-E16
Continuity mistake: A fight breaks out in the prison laundry, and Monk crawls into a giant dryer to hide, pulling the door mostly shut after him. But in the very next shot of the fight raging on, the dryer door is visible in the background - wide open. Next shot after that, it's shut again, and Monk sneaks it open to peek out. (00:42:00)

Mr. Monk Goes to Jail - S2-E16
Continuity mistake: One of the times the prison guard is attempting to pat down Monk, his hands are approaching Monk's abdomen. After a cut to the next shot, his hands are suddenly around Monk's lower legs. (00:05:55)
Mr. Monk Goes to Jail - S2-E16
Continuity mistake: The large blue Nazi/Swastika tattoo on the left side of the head Nazi's neck changes from being neat and symmetrical to uneven during the course of the episode. This is most noticeable when comparing the exercise-yard "you stole the watch" scene to the black-and-white "solving the case" flashback scene.
Mr. Monk Goes to Jail - S2-E16
Continuity mistake: When Monk and Sharona talk to Sylvia in the prison library the second time, the books on her desk change in various shots. At first, you see 3 piles of books, all with blue books on top. In the next shot the blue book closest to her is gone. In the next shot, she's straightening a red book next to her, but it goes back to being crooked.
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