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High King
Ruaidhrí Ó Conchubhair
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Name: Rory O Connor / Ruaidhrí O Conchubhair / Roderick O Connor
Race: Celtic
Profession: High King of Ireland / King of Connachta (Connaught)
Date of Reign: 1166 - 1175
Died: 1198
Father: Toirdealbach Mór
Brother: Cathal Crobh Dearg 'Red-Handed'
Son: Conchubar
Associated
Sites: Dubhlinn (Dublin) 
Athboy
Tailltean (Teltown)
Finglas (battle against
Strongbow)
Monastery at Cong (Clonmacnoise Co. Offaly)
Notable Events during Reign: Anglo Norman Invasion of 1169
Allies: Godred king of Man (Isle of Man)
Enemies: Strongbow (Richard of Clare)
Army: Could command an army 30,000 strong
Rory O Connor became Ard Rí (High King) in Ireland when his predecessor Aodh O Lochlainn died in 1166. Aodh O Lochlainn made some grave mistakes during his reign and the native chieftains of Tirconnell (Donegall) looked to Tirowen (Tyrone) for their leader. The Chiefs agreed to elect Rory as High King and the Districts of Tirconnell, Brefny (Cavan/Leitrim), Meath and the Danes of Dublin submitted to him when he marched on them.
He was widely recognised as the High King and was inaugurated at Dublin. In 1167 he gathered together a council of the ecclesiastics and chieftains where many useful laws for governing the country were laid down. He also celebrated the Fair at Tailltean with 13,000 horsemen in attendance in 1168, which was the last fair held there for many centuries, save a brief revival in the mid nineteen fifties.
Rory was not a very strong leader however and made many strategically disastrous decisions during his reign. When the Anglo-Norman's invaded Ireland with Strongbow as their leader, Rory proved himself to be extremely lacking in leadership. Although Rory and his army of 30,000 men moved against Strongbow in Dublin, they laid siege to the city for two months intending to starve the smaller army of Strongbow out and force a surrender.
Instead of using his numerical advantage and charging the enemy, Rory played a silly waiting game. In the end Strongbow and his smaller army of 600 managed to gain the advantage over Rory by storming his camp and taking the Irish soldiers by surprise. Taken unawares and unprepared most of the Irish army fled and Strongbow was victorious at the battle of Finglas. Remember Strongbow was completely ruthless, he had murdered the entire town of the Waterford Danes when he first arrived, so tales of the slaughter had gone before him and put fear into the hearts of the Irish.
In 1175, fearing that his kingdom at Connaught would be invaded, Rory signed a treaty with King Henry the second of England, in which he ceased to be Ard Rí in exchange for a guarantee of no attacks on Connaught, this treaty was called the treaty of Windsor. As with all treaties made with The Crown (the Native Americans know this to their cost as well) it was broken and Connaught was invaded by Milo De Cogan, who was defeated but afterwards King Henry the Second granted Connaught to De Burgo.
This was a permanent stain on his career and Rory's son Conchubar forced him to resign and retire to the monastery at Cong in 1183. Rory tried to regain his position after his son died but no-one was prepared to support him.
He died at the monastery in 1198.
Source: E. A. D'Alton - History of Ireland.
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