No offense intended ArkInRev, but you seem to be glossing over Jins "moral" side of the argument.
I am absolutely glossing over that because I don't believe that subset of experience is required for AI to beat a human. Or for that matter, a human to participate in the hobby.
Considering enjoyment as being part of the "win" is a subjective and emotional evaluation of a game. It's like Charlie Sheen saying he's "winning." I think there would be many people that would disagree with his subjective valuation that is placed on "winning."
So, dropping AI from the equation for the moment to establish what "winning" is:
One player is a terrible painter, loses every game, makes friends, but then falls undeniably in love with the game and cherishes every moment.
Player 2 is a painting demigod, tactically crushes his opponents like the second coming of Julius Caesar, shows up to games and doesn't interact socially, but does not engage in any emotional aspect of the game. He's a professional or just plays to kill time.
Who beat who?
In my view: Player 2 wins, player 1 gets the "that's the spirit participation ribbon." That's not to diminish or mock player 1, he "gets" the hobby. But player 2 subjectively beats player 1 at painting, and objectively beats them at tactics.
In tournaments, I don't really see a "Who had the most fun? at 40k" category, and even those with sportsmanship categories don't trump the weighting of the technical painting or practical winning categories. As evidenced by any painting or gaming tournament placing no objective value on enjoyment leads me to believe that other players also don't believe that the level of enjoyment is a fundamental component of winning.
So, if AI wins the game, and a machine out paints me he wins. I'm not bothered that I have the consolation prize of "being" despite my inability to overcome that opponent. My esteem isn't bruised by a loss to a machine any more than it is by losing to a human.
I've won games and felt bad about my opponent not having fun. I feel a loss, but I also know that I beat that other person.
When I've lost to AI, either in board games or video games, I know and feel that I have been beaten. I've never dismissed the AI as not really "playing" because it just did as it was programmed. I lost, I had frustrating fun, and I'm OK with my enjoyment of the game. If my opponent feels nothing, that has no impact on my win or loss.
Sure, the AI doesn't have endorphins released to give it pleasure, but I don't think that the chemical "win" in my brain turns my loss into a victory. If an AI is "rewarded" by getting the 1 it's looking for instead of the 0, I don't really see that as a requirement to win. People participate in the hobby for different reasons, and I wouldn't diminish their motivations any more than I would diminish my computer's motivation to get that "1."