George Keith’s long involvement with the Jacobite cause illustrates the trajectory of individual loyalty set against an evolving historical situation. Unlike many of the Jacobites who were Episcopalian, Keith was a religious sceptic. He joined the Rising because he came from a family and a part of Scotland that were traditionally faithful to the Stuarts, subsequently commanding the cavalry at the Battle of Sheriffmuir. The failure of the Rising, and Keith’s subsequent conviction for treason, led to his exile in Spain. Painted between the disappointments of 1715 and 1719, this optimistic portrait presents the confident Commander before a romanticised landscape.