He was noted for his lavish banquets at the top of Killaha Castle, but that all changed after the Cromwellian conquest of Ireland.
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His hereditary responsibility brings him to the Spanish Netherlands, to Bohemia where he takes part in the Battle of White Mountain as a musketeer in captain Somhairle Mac Domhnaill's company, and from there to the Irish College of St Anthony in Leuven (Louvain), in the company of Brother Mícheál Ó Cléirigh and Father Brian Mac Giolla Coinnigh, and finally back to Ireland during the wars of the Irish Catholic Confederation and the Cromwellian conquest of Ireland.
King James 1 restored the castle to the O’Connors in 1607 but in 1651 during the Cromwellian conquest of Ireland, it was again captured, this time by Cromwellian forces under Edmund Ludlow.
In 1649, the town was taken by English Parliamentarians during the Cromwellian conquest of Ireland.
During the Cromwellian conquest of Ireland, in December, 1649, Oliver Cromwell, marched from Waterford to Kilmacthomas during the Siege of Waterford.