Max Hudson

Max Hudson is the main antagonist of the Monk episode "Mr. Monk is on the Air". He was a shock jock suspected by Mr. Monk and his sister-in law of murdering his wife, despite the fact that he was live on the air. He is arguably one of the most hated and cruel antagonists on the show due to his emotional abuse towards Mr. Monk.

He was portrayed by Steve Weber, who also played Jack Torrance in The Shining miniseries.

Personality
Max was extremely vulgar, heartless, selfish, and emotionally abusive. It is stated by his sister-in law, Linda, that his wife, Jeannette, was terrified of Max as he always had a terrible temper, and had even been arrested for assault at one point. It's also implied that he used Jeannete as the butt of his jokes most of the time on the radio (even going so far as to make fun of her death). He had a "welcome" mat that said "Go Away" versus the usual term. He also wrote a book titled Max Hudson: Sex, Lies, and Radio, which Monk described as merely nothing but "toilet water".

His Plan
It was for his heartless nature that  Jeanette filed for divorce. Unfortunately, for Max, a divorce would have cost him around $30 million, so he decided she had to go beforehand. But he needed to get away with it despite his clear motive. Luckily, for him, his neighbor's dog needed watching while they where on vacation to Hawaii. He came up with the idea of offering to watch the dog while they were gone, training him  (being a Jack Russel, which is a very smart breed) to sneak into Jeanette's room through the ventilation window in the basement while she was asleep to turn on the gas fireplace, and leave with the door closed on a certain signal he would give on the radio: "Jiggle me timbers!". He made sure the radio was on in his neighbor's house for the dog to hear. He also prescribed sleeping pills for Jeannete to make sure she would never wake up. The plan worked because the security company's diagrams show the house as being wired and monitored 24/7. Not a single person entered or left the house at any point that night. And since the ventilation window only opens about eight inches, and it was the only window open, no one would ever suspect that he simply hired someone to break in.

One day, after his plan was put in motion, him and his two radio sidekicks, Little Willi (a short person) and J.J (a joke machine) were on break at the radio station  when Max got a call on the other line from a police officer. Max took the call about his wife in the back room, but before doing so, he rehearsed what he was going to say before being informed about her death.

Upon Meeting Monk
While Jeanette's death was ruled as an accident, her sister, Linda, was not at all convinced seeing as to how she never turned the fireplace on and knew Max had the motive, as well as the kind of person he was. After she convicned Monk, he too had suspected Max of murdering Jeanette after investigating the scene of the crime himself. His assistant, Natalie, agreed seeing as to how she disliked him as well,  and would leave stores or restaraunts  any time he was on the air.

Monk and Natalie go to Max's  radio station to question him. Unfortunately, it's while he is on the air and they are both made the butt of his and his sidekicks' jokes before they can get anything out of him.

Monk tries to confront Max twice: one other time at his book signing, in which Max tries to convince him Jeanette's death was suicide, but Monk isn't buying it. And a second time on his radio show live. Things are not going good seeing as to how the jokes Monk had burrowed for the show have not aged well. Things get worst when the conversation leads to them discussing Monk's own marriage. Max uses his late wife's, Trudy's, death to his advantage to mock him even further, with one joke  pushing it too far (you should have called me in to help you with the case-I'm great with solving jigsaw puzzles!). Even Willie and JJ are shocked by this as if there was a line, and he crossed it. This urges Monk to to go berserk and lunge over the table at Max, only to be stopped by security guards who dragg him out. Max, unmoved by this, simply thanks Monk for "stopping by".

After Monk has solved the case, Max arrives at his house, only to find Monk, Natalie, Captain Stottlemyer, Lieutenant Disher, and Linda there ready for his arrest. Before doing so, Monk explaines how he was able to murder his wife by basically using his neighbor's dog as his accomplice. He figured it out when he noticed during the crime scene that a shoe was missing, and that the dog happened to be chewing on one while he was still trying to solve the case at Max's house for the second time. They play a recording of his quote "Jiggle me Timbers!" for the dog to hear, only to dicover that that was the signal for him to sneak into Jeanette's room and turn on the fireplace while she was asleep. The case is closed, and Max is arrested. After he was put in cuffs, Monk dared him to find a joke in the situation, and he could not.