What you get when Middlecreek's finest emigrates into the great Outside.
Born in Middlecreek on the island of Zul'Dare, Henry Caldwell was part of the only community on the island that broke the Esoteric Order's isolationist policy. He travelled with much of his family to Boralus, where he joined the military with his fellow immigrant and childhood friend, Reginald Redpath. Together, they rose through the ranks of the royal guard of the Admirality. It was Redpath who became the captain of the royal bodyguard of Thaumas Proudmoore, while Henry ended up as a protector of Xanthus Alverold.
As his family had converted to Lightism, Henry acted as an informant for the rebel Janus DeMeza. His uncle, Yuric Caldwell, leader of Middlecreek, also supported DeMeza. Yuric was eventually found out and executed, while Henry Caldwell joined the rebellion.
After the Battle of Boralus, Henry Caldwell joined the Kul Tiras Regency Council.