George really made a big mistake
He's no poor naive George.
I never hated the prequels, but George had whored out his IPs to hell and back for all their worth in many ways before selling, so he's not, like, your poor, sensitive, arsty old folk who got duped by the Jew Mouse.
What did him is that he was out of touch. He is a boomer liberal with a boomer liberal mindset and he never abandoned the 70s Hollywood mindset even though it was dead in the water by the time he did the prequels.
In fact, he seems gleefuly unaware that he lucked out of being majorly cucked as early as 1977, during the production of
A New Hope. He was no saintly George who always assumed good in people's hearts, he knew how to play the game in the 70s and early 80s, where he could leverage his luck (and friendship to Spielberg) into doing whatever he wanted.
He should have realised that wasn't the case anymore when, while doing the prequels, the new Hollywood clique did everything they could to fuck him over, from banning people from working with him to running a negative press campaign against him with hit piece after hit piece (what do you guys think all the prequels hate
was? It was always astroturfed. The movies did not get that much hate on the street, only by Hollywood self-proclaimed nerds and critics that eventually managed to peer pressure a lot of fans into hating the prequels through the power of meme).
But he lucked out a second time (the movies were a sucess despite what you might think with all this
everyone hated the prequels in the 00s narrative) so he waved it away and thought it wasn't too bad after all.
He blamed the fans (and not the journos and influencers) on the 'toxicity' and eventually sold it all, thinking that whoever would pick it up would be respectful to his vision and consult him often. That's, basically, how would have it gone if the soldout had happened in the 70s and 80s.
He was also reassured by known faces, Lucasfilm employees and long-runners, like Filoni and Kennedy.
He had never cared about Filoni creating massive continuity mistakes because he did not care about continuity mistakes
at all with EU authors, it just happens most EU authors loved Star Wars and regularly asked him stuff and he had a veto power that was actually powerful (he doesn't seem to understand the difference between ruling over stuff because you own it and ruling over stuff because the people who own it allows you too).
He also never cared about Kennedy resenting him because her dumb ideas and attempts at rising above her station were systematically shut down. He didn't even register that one.
He didn't care about the
massive change in culture in Hollywood at around 2014, he barely noticed it.
He was on a position were Filoni and Kennedy would just be employees who would never challenge him in anything sensible, and he never bothered to actually delve on what sort of people they were or what sort of work they were doing. They were just 'known faces' to him.
So when he's getting pressured by Iger, those two would sweet talk him and he would eat it up. He would go all Trump "Yeah, them guys, that woman, Kennedy, terrific, terrific woman, been working for me for many, many, many years and that other one, the hat one, yeah, Filoni, terrific, amazing, the best writer I've ever had. Must be since he's also been here for a while now"
So, TL;DR George Lucas was massively out of touch, wanting to stick it up to them feisty fans and the idea that Disney (Lemme remind you,
the entertainment company,
the quintessential family friendly american movie magic factory with whom he had already collaborated in the past) would purposefully destroy Star Wars (
the Space Opera, a money printer and a cultural landmark) and fill the production crew with bad agents, deranged activists and malicious individuals that openly hate Star Wars, its fans, its creator and everything it stands for was an utterly alien, unthinkable concept for him to grasp.
In fact, some of us at the time were only vaguely having such an intuition at the news that they'd be gutting the EU, but wouldn't, in our wildest feverish nightmares, come to imagine it would come to this.
It was just a completely alien thought to process, even for those of us who were paying attention at how things were shaping up!
In fact, even some of the individuals involved, who are not, by any means, the sort of people you would lump with Fandom Menace types (J.J. Abrams being the most notable, but there are many others) were also shocked by how things turned. And we're talking a guy who, the second he was informed he was getting his hands on Star Wars, went over to Lucasfilm to pillage and plunder the place like a savage.