No. How much wealth could those individuals create if they couldn't sell the companies on the market and invest that money, and had instead to accumulate dividends? The relationship is symbiotic.
Yes, Trump created wealth, but the point is that his peers would have created even more if he hadn't used that money himself. To make an analogy, I can swim a few laps, but you wouldn't want to have me replace Michael Phelps on your team.
His father, Fred Trump, built a real estate empire of 27.000 apartments in Brooklyn and Queens. Just sitting on those and maintaining and expanding it would have resulted in a fortune many times bigger than he has today.
The bigger point I want to make is that the standard deviation on returns of a single venture like Trump's is so large that you cannot meaningfully compare it to a highly-diversified basket of stocks.
To use your analogy, it'd be like evaluating the effectiveness of a coach in a swimming event by picking a single one of their swimmers and comparing them to the average times of the U.S. Olympic team. Does this necessarily imply anything at all about the skill of the coach?
I disbelieve (1) because of his multiple high-profile bankruptcies.