My family was both Yankees & Southerners. Civil War was a couple hundred years latter but that was truly a war of brother against brother in my family.
They originally landed in VA (Jamestown), first wave and survived. He acted as a liaison between the settlement and the tribes exploring new cultures and territory when he could. Eventually moved to what is now known as Delmarva to get away from population growth and government intervention

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Ancestor seemed to be trying not to get too noticed too much by the King so they moved away from Jamestown and tried to stay out of the limelight. He moved away from the settlement and lived with the Natives establishing commerce and warring with them against other tribes.
This kept him at arms length from Jamestown government except to sell merchandise (primarily tobacco and Native American goods necessary for the settlement), and made him an invaluable resource to the colonies which is why the let him do it.