On paper, Kathleen Kennedy certainly looked like a good choice to head up Lucasfilm. Her connection to so many classic movies, many of which were and still are cultural touchstones, should have made her the perfect choice. She has a list of producing credits that would make geeks and probably most producers drool.
What I think eventually became clear (see The Acolyte) is she rode the coattails of artists and visionaries rather than having a hand in any of the magic that made those examples of creativity appealing. It is not a cut to she has no creative vision of her own. She is an administrator or a bureaucrat. Some people are just like that. That though is the wrong person to oversee an IP.

George Lucas, for all his flaws, had a vision of what Star Wars should be. That vision changed here and there with the passage of time, but he in his heart knew what the Star Wars universe was at a given time. To him it was less than real but more than fiction. I liken it to how the creator of Conan the Barbarian described his creation of the stories. He said that Conan would visit him and tell him stories. I dare say the same thing about George Lucas. He may not have been visited by Anakin or Luke or Han Solo, but he could part the veil and walk in on them or other corners of that universe.
I will even go so far as to say that her decision to remove everything that didn’t appear on the screen into the ‘Legends’ category was the correct move from not only a business standpoint but a creative standpoint. Disney, as a company, would have no desire to get tied up in any possible legal issues that might arise from something that was created before the purchase. Who knows what is covered under copyright law that 20th Century Fox (before getting consumed by Disney) or some random publisher or some random writer might have a claim to. That could certainly muck things up for future projects.
The problem is without a passion or vision for what Star Wars should be she had no ability to find anyone that could replace it with stuff as good or better. The Acolyte? Who thought that was a good idea? Kathleen Kennedy. Ultimately every poor decision and badly received project lays at her feet as the head of Lucasfilm.

Her lack of appreciation for the material or an understanding of the fandom has shown. How? She has announced project after project that has never gotten beyond that initial announcement. Some have simply been quietly forgotten about and pushed aside while others have been openly canceled. That and she blamed the potential audience for disliking what was presented. This “It’s not us. It’s YOU” attitude only further alienated people.
For her lack of vision, I think you can point safely to the sequel trilogy. George Lucas may not have had a plan for the original trilogy films, but he had an idea where he wanted things to end up. Maybe nothing was written on paper, but there was certainly something there guiding it. Each tells an independent story but together form a larger narrative. Star Wars leads into Empire leads into Jedi. You can see a connection even if that connection was not planned out. Not every trilogy needs a plan but there needs to be a guiding hand to keep it all together. Look at the unintended Trek Trilogy of II, III, and IV in the original cast films. Separately distinct movies but together they form a storyline.
She brought in JJ Abrams who has never done service to an intellectual property that is not his own creation. Some would even argue he has run his own creations into the ground. He did his best to overload the senses of the audience with spectacle and nonsense in films that are directionless and often derivative of earlier Star Wars. Tried the same with Star Trek making in both cases pretty movies that have nothing much to them.

Legacy characters that she’s tried to bring back have suffered greatly. Luke is a bitter hermit over his nephew’s bad dream. Indiana Jones became a sad, pathetic old man. Willow was a second or even third-tier character in his own show! If she understood the material, she would understand that nobody wants to see their hero turned into a sad sack. In many of those cases it was like she was trying to replace them with another character. “Here’s the new better more awesome character to replace this character you grew up loving and became emotionally attached to!” I don’t blame any of the performers for taking a job. I think, given a better script, Daisy Ridley could’ve shined. Phoebe Waller Bridge and that other girl from Solo not so much. They are supporting actresses on a good day but the opportunity presented itself in their journeyman careers so they needed to say yes.
She doubled down on replacing the Legend material with new stuff for so long that she was forced to resort to nostalgia to get people to look at projects. Ahsoka. The Acolyte bringing in Darth Plagius in a cave.
I’m not exactly sure how Kathleen Kennedy kept her job. Given a record of increasing failure and being behind the least profitable Star Wars movie EVER you would think that the people at Disney would have moved to fire her in some fashion rather than let her ride off into the sunset. Either she had a very good contract, or Disney is seeking to milk this cow no matter how dry it gets. Ultimately, Katherine Kennedy has done more harm than good for the brand. She has managed to alienate fans to the point that Star Wars is not the money-making machine it once was. Can it change with new leadership? Who knows.

