Democracy is the theory that the common people know what they want, and deserve to get it good and hard. - H. L. Mencken
Yes he does.
Taken out of context, this might have been said by one of Atlas Shrugged' antagonists.
But let me be more explicit. We can have values and thoughts that don't respect success. Sometimes that may mean being made irrelevant, being killed, or even made extinct as a group. Nonetheless, until actual death occurs, we can hold those views.
To some people that is more important than anything else. I like those people. Some are successful, some are not. The universe will erase them, as it will erase us all. But to me while that thought lasts, it is valuable.
Future Trumps can follow some algorithm to have maximum appeal to voters ..
SCOTUS nomination?
He has knowledge of the tech sector and doesn't want to ruin it, he isn't anti-science, he's gay (and thus pro-gay rights), etc.
That said, I think it's profoundly unlikely, since unless I'm not aware of it, he'd be the only supreme court justice with no legal background.