Hence by 1400, many of the descendants of the Anglo-Norman knights had, through intermarriage and adoption of Gaelic customs, become Irish chieftains in all but name. Those who retained their loyalty to the English crown and customs were confined to a narrow strip around Dublin known as the Pale.

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Despite some initial success in conquering its eastern edge, the Normans failed to penetrate the rest of Ulster, the northern province which was inaccessible and remote from the centre of English power in Dublin. Here, the Gaelic polity and society continued as it had done for centuries. Various branches of the Ó Neill family ruled much of it, and in the west of the province, the very north-west corner of Ireland, their rivals the Ó Domhnaill sept were supreme. Each of these had several vassal septs, bound to them by force or tradition. Sub chiefs to the Ó Domhnaill included the Mac Suibhne, Ó Dochartaigh and Ó Gallchobhair families, and the subject of our interest, the Ó Baoighill.

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For much of the 15th and 16th centuries, the history of Ulster was dominated by the conflict between the Ó Neill and Ó Domhnaill dynasties, and by the internal conflicts within these dynasties. The Gaelic system of succession to the chieftainship virtually guaranteed dissension.  Leadership of the sept did not automatically pass from father to son; a new chief was selected from within the derbhfhine, a sort of electoral college composed of men whose father, grandfather or great-grandfather had been the chief. Though a chief could nominate a tanaiste, his preferred successor, a distant cousin could and often did challenge for the title, with the outcome decided by blood and pillage. The English Crown frequently exploited these divisions, offering support to one side or the other in order to promote its own interests and weaken resistance to its colonial expansion.

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Around this time, descriptions of the society and politics of the Gaelic lordships by English commentators depict “the native territories as blighted regions characterised chiefly by the spirit of violence and lawlessness”. To outsiders convinced of the superiority of English centralised government and accustomed to strong control “it was inevitable that the Gaelic and gaelicised lordships would seem disordered, even anarchic, ruled as they were by warlords often at war with their immediate kin as well as with their neighbours and traditional lineage enemies.

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