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Notes -
This kind of thing used to happen, it was the original definition of the word "filibuster": https://en.wikipedia.org/wiki/Filibuster_(military). It has been illegal under U.S. law de facto since the 1794 Neutrality Act, although it wasn't always enforced until the 1850s. So what would actually happen is that the billionaire would be arrested and would lose everything.
Also, what would the billionaire gain? Haiti is a country devoid of human and natural resources, that relies on international aid simply to feed itself.
Even if he wasn't arrested (which he would be), the P.R. for the billionaire would be terrible. The American press would go into a fury at the idea of a billionaire doing an authoritarian corporate fascist take over of a country. They would signal boost every bad thing that happened: Every Haitian killed, every repressive act, every mistake in rule, everything thing with bad optics on the island would be blamed on this billionaire and he would be made to look like a super-villain.
While I agree with your overarching sentiment (wouldn't work, arrests & sanctions to follow quickly behind etc.), it is worth mentioning that Haiti is actually overflowing with natural resources. It is estimated that Haiti may have the largest oil reserves in the world, surpassing even Venezuela. This is in addition to some $20bn in gold deposits, significant copper deposits, and massive tracts of perfectly fertile farmland. This puts Haiti in the unenviable position of many African countries. Namely, a pathetic (read: nonexistent) government, a shocking wealth of natural resources, and abject poverty.
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Was that broken by Texas? Could maybe have selective enforcement constitutional issues (you did say 1850’s).
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