Hugh O'Neill.

In 1559 Conn died, Shane became The O'Neill, Hugh was taken into the protection of Sir Henry Sydney, the Queens deputy, and raised as an English nobleman at Penshurst Place, Shropshire, England. In 1567 Shane's son Turlough succeeded him to the title.

In 1568 at the age of eighteen Hugh O'Neill settled in Ulster, initially he was loyal to Queen Elizabeth, leading a troop of cavalry against the Desmond rebellion in 1569. Again in 1573 he assisted the first Earl of Essex in the attempted colonization of County Antrim.In 1587 he was granted the earl ship of of Tyrone and in 1593 he succeeded Turlough who was in ill health as The O'Neill. At this point he switched his allegiance away from the English, he was now in a position to unite the Irish chiefs in defense of the Gaelic way of life, however in light of his previous actions in assisting the English in their attempts to dominate the country, he may have been distrusted by some of his allies.

In 1595 Hugh O'Neill defeated the English near Blackwatertown County Armagh, he repeated this success in 1595 against his brother in law Sir Henry Bagenal (See Nicholas Bagenal) at Clontibret County Monaghan. Hugh O'Neill's greatest victory came in 1598 when he again met Bagenal this time at Yellow Ford on the river Blackwater, County Armagh, Bagenal was killed and his army defeated.

The 2nd Earl of Essex arrived in Ireland with an army in 1599, he proved to be totally ineffectual and only managed to negotiate a truce, he was replaced by Lord Mountjoy who set about subduing Ireland with great ruthlessness. In February 1601 Essex was executed for treason. Hugh O'Neill enlisted Spanish support for his struggle, in 1601 three thousand Spanish troops landed at Kinsale in County Cork, where they were immediately surrounded by Mountjoy. O'Neill marched his army to Cork where it was totally routed. He retreated to Ulster where he eventually surrendered on March 30 1603.