Massey then began to take an active part in politics on the
Presbyterian side, and was one of the generals who was impeached by the army on the grounds that they were attempting to revive the Civil War in the Presbyterian interests. He fled England in June 1647 and, though he resumed his seat in the house in 1648, he was again excluded by
Pride's Purge, and after a short imprisonment escaped to
Holland. Thence, taking the side of Royalists openly and definitely. Like many other Presbyterians, he accompanied
Charles II to
Scotland. He fought against Cromwell's army at the bridge of
Stirling and
Inverkeithing, and commanded the advanced guard of the Royalist army in the invasion of England in 1651. It was hoped that Massey's influence would win over the towns of the Severn valley to the cause of the King, and the march of the army on
Worcester was partly inspired by this expectation. At the
Battle of Worcester, he was seriously wounded, and when Massey realised that his wounds were dangerously slowing King Charles II down
during his escape, he persuaded Charles to continue without him, although the king was reluctant to leave him. Massey was arrested and imprisoned in the
Tower of London. He again managed to escape to
Holland. While negotiating with the English Presbyterians for the restoration of Charles, he visited England twice, in 1654 and 1656. He was arrested in England for his part in
Booth's Uprising in 1659, but was able to escape for the third time. After his escape, while hiding in London, he encouraged the discontent that led to the soldiers' mutiny over pay on 1 February 1660. ==Restoration==