Respectfully, doctors tend to be the worst at exhibiting DK behaviors. Given their educational history, they tend to vastly overestimate their intelligence in other matters outside what they studied.
If CDC is as cunning as we hope, he knew last year that at some point he was going to have to fire Tom. He either lined up a few BMDs to be able to handle the buyout (I'd guess max 3 knew about this plan....and yes, if you are a billionaire you can stake your AD for $10mm so he knows he's got it if needed) or he started building the file to fire Tom for cause/negotiate down the buyout. Anyone that has worked at a public company knows firing someone takes lots of data points of failure. I'm going to guess CDC probably started building that file in 2019 (drunken behavior at ACC, dickin' a jewelry maker, blow, etc). First official reach out to Urban happened the day after the Tech debacle and terms were agreed to in October.