With Trump, I think this goes way deeper than a learned strategy to claim victory no matter what. Trump has narcissistic personality disorder, and his brain can’t conceive of a situation where he doesn’t win. At his core are such deep-seated insecurities about himself that the only way his brain can cope with itself is to never show vulnerability by creating a fictional narrative in which he’s the winner all the time. It would be incredibly pathetic if it weren’t so terrifying. Someone like him who wasn’t born into extreme wealth would be lonely and broke right now