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 @90bf4d25 You could be right.

I suspect his companies owe debt, not him (because even the dumbest lawyer is smart enough to know business is done through a company)ā€¦ So while I dont think he is nearly as rich as he claims to be.. Im not sure he personally is in as much debt as it may seem either.

That said witht he shit trump has done it is very likely he has or will allow lawyers to pierce the iron veil (A term meaning circumventing protections created by incorperating)ā€¦ and they very well may be able to after him personally,. 
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 @b05df304

Saying the debts are held by his corporations would mean that his shares are worthless. But Iā€™m sure that the corporate veil can be pierced, and that he has debts in his own name as well. 
 @90bf4d25 yea his shares very well may be worthless, but the value of a share can never go negative (into debt)ā€¦ so at best he is broke, at worst they will pierce the cooperate veil and he will be in debt.