Declared an outlaw Both John Stanley and his elder brother, William Stanley (who succeeded their father as Master-Forester), were involved in criminal cases which charged them with a forced entry in 1369 and with the murder of Thomas Clotton in 1376. Butler joined them upon their arrival in Ireland. Because of the success of the expedition, Stanley was appointed to the position of
Lord Lieutenant of Ireland, Alexander to Chancellor, Crull to Treasurer, and Butler to his old position as Governor. 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 Castle. He 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 manoeuvring, turned his back on Richard and submitted to King
Henry IV, the first of the
House of Lancaster.
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
tenure of the
Isle of Man, which had been confiscated from the rebellious
Henry Percy, 1st Earl of Northumberland. In this period he also became
Steward of the Household to King Henry IV, and was appointed by him a
Knight of the Garter. In 1413 King Henry V of England sent him to serve once more as Lieutenant of Ireland. He summoned the
Parliament, which met in
Dublin in November 1413. ==Death and burial==