Donal and Margaret had six sons:[b] —and two daughters:[8] According to English custom he would have succeeded his father as Prince of Carbery at his death in 1567, but brehon law was applied and all his three paternal uncles ruled before him.

[11] Upon his death an inquisition was taken of the family[12] and it was determined that the MacCarthy Reagh was still collecting yearly rents from various Irish chiefs that all totaled £207 16s 11¼d per annum.

[14] Donal na Pipi is widely known due to his conflict with his cousin, Florence, over the succession to the chiefship as Prince of Carbery.

[15] Although it can only be speculated, it seems Donal may have realized that English conquest was by now a sure thing, and the best way (despite his personal ambitions) to preserve Carbery was to opt for surrender and regrant.

The family's native Irish allegiance can hardly be called into question, as just fours years earlier, although Donal na Pipi remained visibly neutral, his cousin fought alongside The O'Sullivan Beare against the English at the Battle of Kinsale.