Charles Middleton, 2nd Earl of Middleton (c. 1640-1719), held several offices under Charles II and James II, being envoy extraordinary at Vienna and afterwards joint secretary for Scotland. In 1684 he became an English Secretary of State, and with Richard Graham, Viscount Preston, he had the difficult task of managing the House of Commons for James II. He was loyal to James after the king fled to France, although he remained in England. where, as the leader of the moderate Jacobites, he sought to bring about a restoration by peaceful means. In 1693 the earl joined the exiled king at St Germain, where he became his Secretary of State; afterwards he held the same office at the court of James Edward, the old pretender, in Flanders and in Lorraine. He was partly responsible for the unsuccessful expedition of the jacobites to Scotland in 1707, and he resigned his office as secretary in 1713. Middleton, who had been created Earl of Monmouth by the pretender, died in 1719. His titles had been declared forfeited in 1695, but they were claimed by his son John, who died unmarried about 1746. The earl was a Protestant, although a lukewarm one, until 1701, when he yielded to the dying wish of James II. and joined the Roman Catholic Church.