It is not known when he returned to Ireland, but Stephen Dunford suggests it was around 1660, after the Restoration of King Charles II to the British and Irish thrones. Like all the other Irish landowners who had been dispossessed for supporting King Charles I of England during the English Civil War, the O'Hanlon family soon realized that there would be no restoration of their property by the new King. In response, Redmond took to the hills around Slieve Gullion and became an outlaw, or rapparee.