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Professor Willow should have just been older Gary Oak
Never directly addressed but occasionally referenced and winked at
Just give him some dialogue like “I’m Professor Oak, but I don’t like being called that. To me, there’s only one true Professor Oak. Just call me Gary, or my nickname Willow.”
Hell, you don’t even need to change the design. If someone said “This is older Gary Oak.” and pointed to Willow, I could buy it. He mellows out when he gets older.