In his first foray into the territory, Hugh sent his lieutenant Aodh Maguire with a detachment to scour the lands of Kilnaboy where he wounded and captured Conor O'Brien, and brought him back to Inchiquin Castle which was given over to Maguire.
Conor O'Brien was at this point acting as a guardian to Dermod O'Brien, 5th Baron Inchiquin who was only 4 years old, and was also in charge of Inchiquin Castle, since the death of the boy's father in 1597.
[1] According to tradition of the Barons Inchiquin, Boetius Clancy, then High Sheriff of Clare, presented to Conor the Spanish Armada table in 1588,[2] made from parts of the wrecked Spanish Armada which had landed in Clare.
The family were then living at Leamaneh Castle, and it was brought to Dromoland Castle when Conor's great grandson Donough had moved there in 1685 and was stored there for over 300 years before being sold at auction in 2018 by Lord Inchiquin.
[note 1] He died on 2 January 1603 (as recorded in the Annals of the Four Masters) and was buried at the monastery of Ennis Abbey.