Actually, to try and help highlight the viewpoint I'm describing, in light of what you're putting out, let me try to frame this stuff a little differently.

Consider something like the CEO of Blackberry. His company is now essentially defunct, in part due to the lack of security and stolen IP, but also because they screwed up their business market dominance by trying to chase the retail market when Apple/google started showing up. His business is toast, and for the sake of argument, let's say the CEO now lives a basic lifestyle, with very little to his name -- most likely he's living pretty damn good though, in reality, but likely not "ultra rich" wealthy.

At the height of his wealth curve, he'd be viewed as a successful business man. At the nadir of his wealth curve, he's a failure.

Business people are often considered successful or not based on their current positions and most recent endeavours, and their overall hoard of wealth. Given that the apprentice 'saved' him, anytime after the apprentice it'd be reasonable to say Trump's a successful business person, even if he was drastically inflating the actual numbers associated with his wealth. Even if he'd previously failed a bunch. There are lots of entrepeneurs that will see their efforts fail a bunch at the start, and if they have enough wealth they'll often eventually succeed. Doesn't make it less of a success when it happens, in some ways.

And now that he's managed to leverage that into owning America, his profit's gone up exponentially -- for both himself and his entire family line. So by American standards, that's pretty successful. And we all know there'll be no accountability, especially not for his family.