He was employed by Sir George Carew and Mountjoy to lampoon the Irish chieftains and instigate enmity between them.
Towards the end of the Nine Years War, taking advantage of the distraction of the English, Chieftain John O’Connor briefly re-occupied the castle only to be put out again in 1603 by George Carew, the Governor of Munster.
This period also saw the first military interest in the island when Sir George Carew ordered a road to be built across the island to transport the pro-English forces to the Siege of Dunboy.
George Carew, 1st Earl of Totnes (1555–1629), Baron Carew of Clopton, served under Elizabeth I and was appointed President of Munster, son of the Dean of Exeter
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George Carew, 4th Baron Carew (1863–1926), younger son of Robert Shapland Carew
Thereafter, the young members who had played their various sports only at their respective schools and at the small, uneven Holetown Elementary School's play ground, invited retired Police Captain Eustace Simmons and former West Indies Cricketer George Carew, both Holetown residents, to be the senior mentors of the young club.
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The queen's secretary, Sir Robert Cecil, advised the President of Munster, Sir George Carew to take good pledges of Fitzgibbon, "for, it is said, you will be cozened by him at last".