Yes, I could imagine Trump doing well about 2500 years ago in a setting of a Large Port CityVillage in Greece, with rich resources and land to build up. Trump is a Wealthy Villager who can make things happen for himself by force of will-power. He likes talking to people that can make things happen, especially if they are strong characters. He is outspoken about strict laws that should be enforced on people that he deals with, but adopts a looser interpretation of law for himself.
He likes to own big expensive constructions including Stone Bridges for tax collection, Cross country roads and port infrastructure to collect travel and usage taxes from fishing and other boats. Trump is a talented story teller and can present multiple versions of a story with passion and vigour. He will say that he does all this for the people, and in return he demands complete loyalty and strong support. He wants to be known as The Man with the Money, who knows other people with money, and also he has a very loud voice, from which he can get things if you are angry and loud enough.
All of the assets held in Trumps name is owned by Alexander, his great friend and Leader of A Big Island - close by. Alexander and Trump did a deal that suited both of them at the time. They thought of it while holidaying at Big Beach where they agreed on a debt deal. Right now business is doing well since the past few years after the drought when lots of people died off and Alexander got his hands on lots of money and Trump had good use for it to build up his land. This is like 2000 years before Robin Hood came along.
