Thought this was an interesting insight from someone (Stephanie Cegielski, formerly the communications director of the Make America Great Again Super PAC) who knows Trump pretty well:
"He doesn’t want the White House. He just wants to be able to say that he could have run the White House. He’s achieved that already and then some. If there is any question, take it from someone who was recruited to help the candidate succeed, and initially very much wanted him to do so. The hard truth is: Trump only cares about Trump. And if you are one of the disaffected voters — one of the silent majority like me — who wanted a candidate who could be your voice, I want to speak directly to you as one of his biggest advocates and supporters. He is not that voice. He is not your voice. He is only Trump’s voice. Trump is about Trump. Not one of his many wives. Not one of his many “pieces of ass.” He is, at heart, a self-preservationist."
Actually, that first part is what I was saying in the first stages - that he didn't want to win, he just wanted to be in the game, for "brand" purposes, and that eventually he'd get out, but would have achieved what he wanted. Only he's stayed in it, so I figured that assessment was wrong. If she's right, the fact that he simply can't beat Hillary isn't a bad thing from his perspective....