Revealing mistake: In the scene where the desks in the office are re-arranged, you can see that all the computers are on but none of them connect to any power point. NB: You can vaguely see that one of the computers is supposedly on Youtube while another is on Google Maps.
Factual error: When Monk visits the prison for the first time, he is searched, passed, and has a mini-panic attack because people have touched him. Sharona steps forward to comfort him, and she puts her arms around him. This is a very serious breach of procedure and it is not possible for the guards to miss it, because Sharona has not been searched. It's a common technique for trying to pass contraband called 'a touch through' - a person with an item to be smuggled into the prison (drugs, usually), passes them on to a person who has been searched and is therefore 'clean'. Monk would be taken back to the guard's station to be searched again. He would not be allowed leniency because the guards happen to know or to like him - visitor ingress and egress is always done under CCTV and the guard would know he was being watched - quite possibly by someone who doesn't know who Monk and Sharona are.
Trivia: The flight attendant Monk drives crazy in 1-13 is played by his real-life wife. She also plays Sheriff Butterfield in "Monk visits a farm"and the crazy cat lady in 8-14.
Question: Why would it have been political suicide if it was discovered that Mayor Nicholson was secretly meeting with Cusack to end the garbage strike? If anything, if the people found out that they were meeting to find a way to end the garbage strike, wouldn't that have made everybody happy considering how much garbage was piling up all over the city?
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