Rather than intended to pass wealth along to the earliest investors, Trump's scheme is to inflate his own apparent wealth. But if he had to break down the pyramid scheme he would end up owing.
This article talks about how Trump cannot divest:
Maybe the Answer Is That He Can't Divest
By Josh Marshall
Published December 8, 2016, 7:25 PM
Since Donald Trump's surprise election one month ago, there's been a bubbling conversation about the mammoth conflicts of interest he will have if he is running or even owning his far flung business enterprises while serving as the head of state. I've suggested that the whole notion of 'conflicts of interest' doesn't really capture what we're dealing with here, which is really a pretty open effort to leverage the presidency to expand his family business. But a couple things came together for me today which make me think we've all missed the real issue.
Maybe he can't divest because he's too underwater to do so or more likely he's too dependent on current and expanding cash flow to divest or even turn the reins over to someone else.
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Since we don't have Trump's tax returns, there's just a huge amount we don't know about his businesses. What we do know is that Trump appears to wildly exaggerate the scale of his wealth and exhibit a stinginess that is very hard to square with a man of the kinds of means he claims. A heavily leveraged business, one that is indebted and dependent on cash flow to keep everything moving forward, can be kind of like a shark. It has to keep moving forward or it dies.
Perhaps Trump simply doesn't feel like he can trust anyone else to keep the whole shambling enterprise afloat. More plausibly, and consistent with Trump's history over the last couple decades, Trump's business is dependent on an ever expanding number of deals not just to grow but to stay afloat at all. It is certainly plausible that if Trump simply sold off his company in toto, he'd be in debt. Maybe there wouldn't be anything left to put in a blind trust.
http://talkingpointsmemo.com/edblog/maybe-the-answer-is-that-he-can-t-divest
And:
Why Trump Won't Use A Blind Trust And What His Predecessors Did With Their Assets
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