The son of John Massey of Coddington, Cheshire, Edward Massey became a professional soldier and military engineer in the Dutch service, then returned to England in 1639 as a Captain of Pioneers in the army raised by Charles I against the Scots in the Bishops' Wars. As a devout Presbyterian, Massey was disturbed at the King's toleration of Roman Catholics and sided with Parliament on the outbreak of the First Civil War in 1642. He was commissioned lieutenant-colonel to the Earl of Stamford. Early in 1643, Massey was promoted to colonel and appointed governor of Gloucester. He repaired the city's derelict defences and conducted operations against local Royalists.
After Prince Rupert captured Bristol in July 1643, Gloucester was one of the few remaining Parliamentarian strongholds in the West. King Charles led the main Oxford army to besiege the city in August 1643, possibly believing that Massey was ready to come over to the Royalists. However, the resolute defence by Massey and the citizens of Gloucester had an inspirational effect on London, where new regiments were raised to march to its relief. Under the command of the Earl of Essex, the London regiments arrived at Gloucester on 5 September and the Royalist army withdrew. Massey's small garrison was said to be down to its last three barrels of gunpowder.
Despite a bitter feud with leading members of the committee for Gloucestershire over the control of local forces, Massey fought tirelessly against the Royalists in his region throughout the winter of 1643 and spring of 1644 and was finally appointed commander of Parliament's Western Association army. When the New Model Army was formed in April 1645, Massey retained an independent command. He captured Evesham in May 1645 which broke up Royalist lines of communication between Oxford and Worcester. Massey then marched against Lord Goring's army. Although his forces were not strong enough to relieve the siege of Taunton, he co-operated effectively with General Fairfax in the campaign leading up to Goring's defeat at the battle of Langport in July 1645.
After the defeat of the Royalists in the First Civil War, Massey became active in the political struggle between the Independents and Presbyterians. His troops were disbanded by order of the Independent majority in the House of Commons in October 1646, but Massey himself was elected recruiter MP for Wooton Basset and emerged as a resolute Presbyterian. In June 1647, he was one of the Eleven Members denounced by Army leaders. The following month — as Presbyterian MPs prepared to defy the New Model Army — Massey was appointed commander of the London militia. But when the Army occupied London in August 1647, Massey fled to the Netherlands with his associate Sydenham Poyntz. He resumed his seat in the House of Commons in August 1648, only to be excluded at Pride's Purge the following December. He was imprisoned in St James's but escaped to the Netherlands in January 1649.
After denouncing the execution of Charles I, Massey came over to the Royalists as a leading representative of the English Presbyterians. In 1651, he joined the English contingent in Charles II's Scots-Royalist army with the rank of lieutenant-general. When Charles marched into England in August 1651, Massey accompanied the Earl of Derby into Lancashire where they tried to rally support for the Royalist cause. A few days before the battle of Worcester, Massey was badly wounded when Major-General Lambert captured the bridge over the River Severn at Upton. Too weak from his wounds to fight at Worcester, Massey fled with Charles after the battle. He got as far as Droitwich, but was unable to keep up and was taken prisoner. From November 1651, Massey was confined in the Tower of London. In August 1652, he escaped by climbing out of a chimney and once again got away to the Netherlands.
Massey joined Charles in exile on the Continent. He became active in soliciting support for the Royalist cause amongst Presbyterians and made secret visits to England in 1654 and '56. In 1658, Massey was associated with Lord Mordaunt and other Royalist conspirators. He returned to England in March 1659 and tried to incite an uprising in Gloucestershire as part of a series of insurrections planned to take place simultaneously around the country. However, Massey was arrested by the Gloucester militia on 31 July and only Booth's Uprising in Cheshire went ahead. Once again, Massey succeeded in escaping abroad. He returned to England in January 1660 and caused a riot in Gloucester when he sought election to the Convention Parliament in March. Duly elected, Massey worked tirelessly for the Restoration. Charles II rewarded him for his services with a knighthood, a grant of money and lands in Ireland.
References:
G.N. Richardson, Sir Edward Massey, DNB, 1894
Andrew Warmington, Sir Edward Massey, Oxford DNB, 2004.