Bankruptcies often mean creditors left unpaid. I have been left holding the bag when such "smart guys" take advantage that way. Smart -- but bad.
Trump has a 'Midas Touch' and some simply cannot stand the notion.
The ability to amass wealth doesn't mean that person doesn't have poor judgment. As for Trump's vaunted 'Midas Touch,' acknowledge in your heart please that you think of it as such because of a 10-year media marketing (TV, inspirational books) "personal brand" that "the Donald" has cultivated. That personal brand has cropped and removed the full context of some 38 dozen U.S. billionaires, where Trump is a third-rate Midas if a first-class self-promoter.
I do grasp the notion that bankruptcy typically means that somewhere somebody does not get paid.
Of course that just means that the system is something which is one that mirrors life, inherently unfair and in the smaller sense unpredictable.
Bankruptcy options, at least in America, are available to others than Trump, and many have taken advantage of the laws associated.
Focusing on Trump's maneuvers in finance minutiae is a waste of time. If not him, then some other.
In the larger sense, unfettered Economics as is life, is rather predictable.
Some will rise to the top.