Named after Prince James Francis Edward Stuart, the Old Pretender, Keith was the son of committed Jacobites. He took part in the failed Rising of 1715, after which he was forced into exile on the continent. From Paris he travelled to Spain, became involved in the failed Jacobite expedition of 1719 and later joined the Spanish army. In 1728 he set out for service in Russia, where he spent nearly twenty years as an officer. Too busy to make any contribution to the 1745 Jacobite Rising, in 1747 Keith joined the army of Frederick the Great of Prussia. He died fighting, having been mortally wounded at the battle of Hochkirch. This portrait was painted in Berlin, where a street is named after him.