Jeremy Hightower

Before the first Andals reached Westeros, Jeremy Hightower already ruled Oldtown as head of his house.

With Highgarden covering the city by land, Jeremy turned his attention to the sea. He had a fleet built larger than any raised before it, meant to escort Oldtown's trade beyond its own coastline.

He put it himself: "Highgarden guards our backs, so we can look outward, to the sea and the lands that lie beyond." The wager paid off, and under his rule Oldtown's wealth came to double.