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Regarding Trump, he really has nothing to do with anarcho-capitalism. He's definitely on the authoritarian populist side, and the only an-caps supporting him are either (a) literally cryptofash (b) view him as slightly better than the Democratic offerings on things like taxes.

Escobar, on the other hand, raises a good point. A truly successful, IRL an-cap organization probably looks a lot like a drug cartel/crime syndicate except existing crime syndicates don't mind violating the non-aggression principle or working with governments because they are fully motivated by profit without concern for theoretical moral principles. An an-cap crime syndicate would have to obey moral imperatives, which raises the question: why would they?