The Nine Years War, in which O’Neill, O‘Donnell and other Gaelic lords united and almost succeeded in turning the tide of growing English dominance, filled the final years of the 16th century. As the 17th century opened, the alliance was still holding, and had some success in achieving dominance over their English and Irish adversaries. Though there aren’t details of their specific activities, the O’Boyle forces under Taidhg Óg would have been an important component of the army of Hugh Roe – ‘Red Hugh’- O’Donnell.

​

But following the defeat of Kinsale and the departure for Spain of Hugh Roe, where he died in 1602, things took a turn for the worse. Hugh Roe’s brother Rory succeeded as chief of the O’Donnells, though opposed by Niall Garv, his cousin and brother-in-law, who had expected to be rewarded for his support of the English during the war. Unable to assert his authority convincingly Rory was in a weak position to negotiate a good deal under the terms of the settlement that ended hostilities.  

​

Rory tried to restore the clan’s fortunes, but seems to have antagonised his supporters in the process. To support his extravagance Rory had mortgaged much of his land to Dublin merchants, and he created more animosity by granting land and fisheries to his creditors over the heads of his sub-chieftains. He submitted to the Crown (i.e. agreeing to rule according to English law and accepting the introduction of English administrators) and for this he was given the title of Earl of Tyrconnell, but had to relinquish some of his power over his former sub-chiefs.

​

The English believed that he was trying to deprive the sub-chiefs of their traditional possessions. Lord Deputy Chichester reported to London that “diverse gentlemen claiming freehold in the county as namely the three septs of the McSweeneys (Banagh, Fanad & Doe), O’Boyle and O’Gallagher, but these men passed over their rights (if any they had) to the earl (as is said) which he got from them, contentiously and by unworthy means”[Hill, 1889].  

 

The commissioners appointed by the English to enforce the agreements insisted that he rectify this injustice and “name them to be freeholders of part thereof, reserving their ancient rights in certainty”[McCavitt, 1994]. Rory conceded defeat and among the 549 ‘Gentry and Yeomen of Tyrconnell’ listed in the Pardon Rolls who were to be confirmed as freeholders of their lands there were forty-two O’Boyles (and three ‘MacBoyles’).  Confirming landholders (usually the leading members of the sept) as freeholders under English law was part of the English strategy to break the chieftain’s power over them as they would owe him only an annual money rent, not the onerous exactions of produce and military support that the chieftains demanded under Gaelic law.

​

We can speculate that these forty-odd O’Boyles represent the upper echelons of the sept, and give us the first indication of its population size.  As people claiming freehold of the land they occupy, they probably have substantial holdings. It is likely that each of them would have a number of sub-tenants who in turn would have landless labourers (who may or may not be O’Boyles) to do the actual work. In total, including dependents, this could amount to many hundreds of people and maybe a thousand or more.