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When it all falls apart, he doesn't need a bailout. He leaves his investors holding the majority of the lost equity, pays off his portion, writes it off and carries it forward, and uses it to reduce his tax bill in upcoming years when he'll have a bunch of government contracts.
All of this looks stupid if you assume he's trying to run a profitable business. But he's not. He's moving cash flow through as many other of his own ventures that he can, and he'll cannibalize the rest. The only people who will actually lose money are normal citizens who will have to make up the list tax dollars.