Background
He was born in Herefordshire, England. Oldcastle's date of birth is unknown, although dubious and possibly apocryphal sources place it variously at 1360 or 1378. He was the son of Sir Richard Oldcastle.
He was born in Herefordshire, England. Oldcastle's date of birth is unknown, although dubious and possibly apocryphal sources place it variously at 1360 or 1378. He was the son of Sir Richard Oldcastle.
In 1401 he served under Henry IV in the Welsh marches, where he helped to suppress the Glendower revolt and at which time he undoubtedly became acquainted with Henry's son, the prince of Wales, later Henry V.
A respite of 40 days was allowed him in the hope that he might recant, but before that time had elapsed, Oldcastle mysteriously escaped from the Tower of London.
Oldcastle eluded capture for almost four years and was said to be the instigator of several other Lollard conspiracies.
Taken to London, he was condemned by Parliament as an outlawed traitor and heretic and "hung and burnt hanging" on December 14, 1417.
Oldcastle was fiercely hated by his orthodox contemporaries, both as a heretic and as a traitor, but with the later rise of Protestantism he became a martyr.
In 1408 he married Joan, the heiress of Cobham — his third marriage, and her fourth. This resulted in a significant improvement of his fortune and status, as the Cobhams were "one of the most notable families of Kent".