Hugh Boy MacDavitt

Hugh Boy MacDavitt (Irish:Aodh buidhe Mac Daibhéid) was a Gaelic Irish warrior from Inishowen. He was the brother of Phelim Reagh MacDavitt and the foster father of Sir Cahir O'Doherty, the eldest son of the O'Doherty chieftain, Shane og O'Doherty and his wife Elizabeth McSweeney; Shane og ruled over Inishowen from 1582 until his death in January 1601.

For reasons unclear in the surviving period records, Hugh Boy had left Inishowen in the late 1500s and joined the Spanish infantry, serving as a soldier in Spain's forces in Flanders for more than a decade. He swiftly advanced through the ranks, attaining at least the rank of lieutenant.

In 1594, when The Great Hugh O'Neill, unhappy that the English were refusing to nominate him as Lord President of Ulster, openly declared hostility against English rule in Ireland (thereby initiating the Nine Years War), O'Neill sent an emissary to the continent (one of Hugh Boy's brothers, apparently Shane cron) to request that Hugh Boy return to his homeland, to help O'Neill train the Irish Confederates in modern pike-and-shot combat. Hugh Boy agreed, submitting a request to the Spanish military command for license to leave his unit, a request that was granted in the fall of 1594. English spies uncovered this request, warning the English Privy Council that, given his status as a seasoned continental soldier and officer allied with Spain, Hugh Boy was a serious danger to English progress in Ireland, and perhaps the best trained soldier amongst the Irish.

Upon Hugh Boy's return to Inishowen, he was inaugurated as chieftain of Clann Daibhéid, a sept of the O'Dohertys apparently serving as hereditary counselors, emissaries, and teachers for the O'Doherty leadership based at Elagh Castle. The O'Doherty chieftain, Shane og, allowed Hugh Boy to occupy Burt Castle, which Hugh Boy refortified with modern gun turrets along the bawn wall, and five cannons to repel attackers.

Given Hugh Boy's status as an officer in the Spanish infantry, he maintained contact with his superiors after his return to Ireland. He served as an interpreter when Spanish emissaries visited the Irish confederate leaders and toured the country while assessing the situation in Ireland and planning the eventual landing of Spanish forces in Ireland (realized in September 1601, when 3,400 troops landed at Kinsale). Hugh Boy also personally negotiated with two kings of Spain for shipments of modern armaments that where transported by ship into Killybegs, County Donegal.

In the fall of 1600, Red Hugh O'Donnell had previously attempted to take back the O'Doherty's main castle at Elagh (along with Culmore Fort) by bribing the English officers who held these strongholds (a tactic O'Donnell had employed successfully previously), but the English officer revealed the plot to his superiors.

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