Despite their similar backgrounds and views, Middleton pursued him with considerable vigour, reportedly because his father died when Montrose's men set fire to his house.

However, viewed by Charles II as a capable and reliable soldier, he was compensated with two key strategic commands, first Rochester Castle, then English Tangier where he died in July 1674.

[3][4] In early life Middleton served as a soldier in France; later he fought against Charles I both in England and in Scotland, being especially prominent at the Battle of Philiphaugh and in other operations against James Graham, 1st Marquess of Montrose.

[1] Middleton held a high command in the Engager army which took part in the Second English Civil War and was taken prisoner at the Battle of Preston in August 1648.

[2] In 1653, Middleton was chosen to lead a projected Scottish rising; he reached Scotland in February 1654, but the participants were deeply divided and the revolt ended in defeat at the Battle of Dalnaspidal in July.