Younger son. Isabel Lathom's second husband.
He was Justiciary of Ireland, and Lord Lieutenant of Ireland. In 1386 he was appointed deputy to Robert de Vere, Earl of Oxford, in the government of Ireland, and subsequently held other offices under the Crown.
He was also Justice of Chester, Controller of the Household, Steward of the Houeshold, Steward of Macclesfield, Governor of the City and County of Chester, Constable of Windsor castle. In 1405 he was granted the Isle, castle, pele and Lordship of Man, forfeited by the Percys. In 1406 he obtained a license to fortify his house at Liverpool called "The Tower".
In 1385 he married Isabel Lathom, heir to the extensive lands of her father Sir Thomas Lathom, in south-west Lancashire. The marriage took place despite the opposition of John of Gaunt and gave Stanley the sort of wealth and financial security he could never have hoped to have had as the younger son in his own family. Stanley had four sons, John, Henry, Thomas and Ralph as well as two daughters.
The year 1386 saw his first appointment in Ireland as deputy to Robert de Vere, Duke of Ireland. In 1389, Richard II appointed him justiciar of Ireland, a post he held until 1391. He was heavily involved in Richard's first expedition to Ireland in 1394–1395.
Throughout the 1390s he was involved in placating possible rebellion in Cheshire. Between 1396 and 1398 he served as captain of Roxburgh. Stanley took part in Richard II's expedition to Ireland in 1399. However, on his return to England, Stanley, who had long proved adept at political manouevring, turned his back on Richard and submitted to Henry IV of England.
Under the Lancastrians
Stanley's fortunes were equally good under the Lancastrians. He was granted lordships in the Welsh marches, and served a term as lieutenant of Ireland. In 1403 he was made steward of the household of Henry, prince of Wales, (later Henry V). Unlike many of the Cheshire gentry, he took the side of the king in the rebellion of the Percys. He was wounded in the throat at the Battle of Shrewsbury.
In 1405 he was granted the Lordship of the Isle of Man by which had been confiscated from the rebellious Henry Percy, 1st Earl of Northumberland. In this period he also became Steward of the king's household, and was elected a Knight of the Garter. In 1413 King Henry V of England sent him to serve once more as Lord Lieutenant of Ireland. He died at Ardee, county Louth in 1414. His body was returned to Lathom and buried at Burscough Priory near Ormskirk.
During his career Stanley held the following offices:-
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