A supporter of the Lancastrian cause, he was present at the Battle of Towton in 1461 where his elder brother was killed. He succeeded his brother to the title, but was forced to go on the run after this heavy defeat. Taking shelter in either Cumbria or Scotland he then crossed over to Ireland where there was still considerable support for his cause in Tipperary and Kilkenny. After raising a force amongst them he was confronted by the pro-Yorkist head of the Dublin government, Thomas Fitzgerald, Earl of Desmond. The two clashed at the Battle of Piltown in 1462, which ended in a decisive Yorkist victory. Ormond's army suffered over a thousand casualties.