Career
He was master of the ordnance and a knight of the shire (MP) for Leicestershire from 1529–1535 in the reign of Henry VIII. He was also in 1529 appointed deputy in Ireland to Henry's son, the duke of Richmond, the nominal lord lieutenant of that country. He crossed over in August 1529, but his power was so circumscribed by instructions from Henry that the head of the Fitzgeralds, Gerald, 9th earl of Kildare, and not Skeffington, was the real governor of Ireland.
This state of affairs lasted for three years and then in 1532 the deputy was recalled. In 1534, Kildare being in prison in England and his son Thomas, afterwards the 10th earl, being in revolt, Skeffington was again appointed deputy, at approximately 70 years of age. After some delay he landed at Dublin in October 1534 and marched at once to relieve Drogheda, but further progress in the work of crushing the rebellion was seriously delayed by his illness. However, in the spring of 1535 he was again in the field. He took Maynooth Castle, killing and executing the entire garrison. The heavy artillery used by him on this occasion earning for him his surname of "The Gunner"; he forced some of Kildare's allies to make peace and captured Dungarvan.
He died in Dublin on 31 December 1535, and was buried in St. Patrick's Cathedral. he was succeeded by his eldest son Thomas.
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