Jamie Winn was the brother of Rodney Winn, son of Jim Winn and Lilian Winn, grandson of Winifred Winn and Captain Rodney Winn, and descendant of Edmond De Winn, Evelyn De Winn and Caran De Winn. Jamie grew up and resided several years in Ceylon with his family. He eventually relocated with his family back in Chapelvale after the village was saved from destruction. He was fourteen in 1896.