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There’s no way in hell his vision he had for his network included all of his radio friends turning their backs on him, never getting good guests and his audience abandoning him. It’s why he goes so hard on the politics angle - he retains what’s left of his meager audience that way.He's bitter. He can scream "I've been over here eight fuckin' years! Real failure, huh!", but it's clear he expected a lot more out of his shitty media empire. All his "friends" are gone and all he has left are a roster of increasingly embarrassing Bobo-tier retards. He downsized his shitty albeit still large home into some thrown together hovel down south, where he'd never been before, somehow picked the blackest fucking city to throw it up in, and clearly never intends to leave it once he settles in.
No more high stakes gambling, no more wild compound parties. No more "funniest guy to never do stand-up!", no more rubbing elbows with celebrities on occasion. Who wouldn't be bitter at that point?
This was not what he had in mind but he has to pretend everything is fine.