 He was, however, opposed by St. Leger and Fitzwilliam, and despite a loving attempt on the part of his wife to obtain his freedom he remained in prison till 1591–2.During the last great rebellion that convulsed Ireland in Elizabeth's reign he, perhaps more from compulsion than free choice, threw in his lot with the rebels; but the evident ruin that confronted him and the loss of his castle of Lixnaw so affected him that he died shortly afterwards, August 1600.He was buried with his uncle Donald, earl of Clancar, in the Grey Friary of Irrelaugh in Desmond.