Background
He was the son of John Tiptoft, 1st Baron Tiptoft, and Joyce Cherleton, co-heiress of Edward Charleton, 5th Baron Cherleton. He was notable for his education, studying at University College at Oxford University from the ages of 13 to 16.
He was the son of John Tiptoft, 1st Baron Tiptoft, and Joyce Cherleton, co-heiress of Edward Charleton, 5th Baron Cherleton. He was notable for his education, studying at University College at Oxford University from the ages of 13 to 16.
He was known as the Butcher of England. He enjoyed a brilliant early career. After being created Earl of Worcester on 16 July 1449, he was employed in a number of official posts, first as Lord High Treasurer (1452–1454) and then as Lord Deputy of Ireland (1456–1457).
He then departed on a pilgrimage to the Holy Land, and returned by way of Italy, where he stayed for two years, studying in Padua.
There he gained a considerable reputation as a scholar of Latin. Most notably, as Lord High Constable (1462), he presided over trials which resulted in the attainders and executions of Lancastrians, an office which he carried out with exceptional cruelty, having them beheaded, quartered, and impaled.
In 1464 he was appointed Chancellor of Ireland for life and in 1467 he again became Lord Deputy of Ireland, and brought about the execution of Thomas Fitzgerald, 7th Earl of Desmond. Upon the Readeption of Henry VI in 1470, Tiptoft was unable to escape with Edward IV and his supporters.
He was captured by the Lancastrians and beheaded at the Tower of London, attainted and his title forfeited.
His last act was to ask the executioner to chop off his head with three blows, for the sake of the Trinity.