Tiptoft, John (1427–70), earl of Worcester , lieutenant and chancellor of Ireland, was eldest son of John, Lord Tiptoft, and Joyce, daughter and coheir of John, Lord Cherleton of Powis, and stands out as one of the most educated magnates of his generation. He had rooms in the University of Oxford (1440–43) and later went to study in Italy, relinquishing his place when he inherited his father's lands (January 1443); he inherited his mother's lands after her death (September 1446) and was given livery of his lands in July 1447. He was created earl of Worcester in July 1449 and emerged as an important figure in the 1450s, serving as treasurer of England (April 1452–March 1455) and as a member of the privy council from 1453.
Worcester was one of the group of magnates appointed to keep the sea in April 1454 and one of the commissioners who invested the king's son Edward as prince of Wales in the same month. Though appointed as an ambassador to Rome in August 1457, he was not sent. He went on pilgrimage to the Holy Land (May–September 1458) and settled in Italy afterwards, travelled throughout northern Italy, and studied at the university of Padua; he was also sent as ambassador to Rome (May 1459). He remained away from England for the last years of the reign of Henry VI, but returned (September 1461) and gave his loyalty to the new king, Edward IV. He was rewarded with several offices during the 1460s: chief justice for north Wales (November 1461–August 1467), constable of the Tower of London, constable of England (February 1462–August 1467), and steward of the king's household. He was also sent to treat with Scotland (1462) and Brittany (1464). As constable, he was responsible for the trial and execution of John de Vere, 12th earl of Oxford, and de Vere's eldest son as Lancastrian supporters in 1462.
His first connection with Ireland came when he was appointed chancellor of Ireland for life (January 1464). When complaints were levelled against Thomas fitz James FitzGerald (qv), 8th earl of Desmond, in 1464, the king was apparently prepared to remove Desmond in favour of Worcester, who was appointed deputy lieutenant in May 1465. However, the appointment was not given effect, and in 1466 Worcester was sent to Wales to capture Harlech castle but failed. He was reappointed deputy lieutenant of Ireland in the spring of 1467 and was in Ireland by October of that year. His first action was to call a parliament to meet in Dublin in December 1467.
Worcester seems to have enjoyed good relations with the earls of Kildare and Desmond in the first session of the parliament, but in the second session, held in Drogheda, he charged the two earls with treason and imprisoned them. Desmond was executed on 15 February 1468, an act that served to shock and horrify both Gaelic and Anglo-Irish, and resulted in the invasion of Meath by Desmond's brother Garret. Thomas fitz Maurice FitzGerald (qv), 7th earl of Kildare, was not executed: he escaped with the aid of Roland FitzEustace (qv), Lord Portlester, and was pardoned by Worcester in an attempt to pacify the country. The reasons for Desmond's execution are unknown, but it is clear that it could not have happened without royal permission. It seems clear that the complaints about Desmond and his ‘Irishness’ had been accepted at some level by the king and that Worcester had been sent to deal with the matter. Unfortunately he chose to use the harsh methods common to England in this period, which served only to inflame the whole lordship. The rest of his period as deputy was spent trying to contain the problems caused by the execution of Desmond, but he never lost the support of the king.
He returned to England in the winter of 1469–70, supported Edward IV against Warwick and Clarence, and was rewarded with the offices of constable of England, treasurer, chamberlain of the exchequer, and lieutenant of Ireland. His extremely harsh treatment and execution of Warwick's supporters in Southampton in 1470 earned him the name of ‘the Butcher’ and he was one of the few Yorkist supporters to be executed in the brief period in which Henry VI regained the throne (1470–71). He tried to hide from the Lancastrians, but was caught and condemned by the new constable, John, 13th earl of Oxford (son of the man he executed in 1462), and was executed on 18 October 1470, a day late because the crowds were too great on 17 October. Worcester was buried at Black Friars in Ludgate, and a monument was built to him in Ely cathedral. Oddly enough, he was not attainted and his lands passed to his son, Edward, the child of his third marriage.
Worcester was in many ways a study in contrasts, an educated man and scholar who left a library to the university of Oxford in his will. He was also an extremely loyal man who tended to take an extremely harsh line in legal matters, which earned him few friends and probably led to his execution. His execution of the earl of Desmond was a mistake brought on by his attempt to deal with Irish conditions using English methods, and served only to alienate the earls of Desmond for the next seventy years.