He was prosecuted for heresy against the Church, and escaped from the Tower of London, after which he allegedly plotted against his old friend Henry V. He was captured and executed in London, after which he became a martyr. He is presumed to be the basis of William Shakespeare's character Falstaff, whose name in earlier versions of the play was Oldcastle.
Sir John's date of birth is unknown, although dubious and possibly apocryphal sources place it variously at 1360 or 1378. Oldcastle is first mentioned in two separate documents in 1400, first as a plaintiff in a suit regarding the advowson of Almely church, and again as serving as a knight under Lord Grey of Codnor in a military expedition to Scotland. In the next few years Oldcastle held notable positions in the Welsh campaigns of King Henry IV of England against Owain Glyndŵr, including captaincy first over Builth Castle in Brecknockshire and then over Kidwelly.
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". The marriage brought Oldcastle a number of manors in Kent, Norfolk, Northamptonshire and Wilts, as well as Cooling Castle, and from 1409 until his accusation in 1413 he was summoned to parliament as Lord Cobham.
At some point in his military career Oldham became a trusted supporter of Henry, the Prince of Wales, later to become King Henry V, who regarded Sir John as "one of his most trustworthy soldiers". Oldcastle was a member of the expedition which the young Henry sent to France in 1411 in a successful campaign to assist the Burgundians in the Armagnac-Burgundian Civil War.
Lollardy had many supporters in Herefordshire, and Oldcastle himself had adopted Lollard opinions before 1410, when the churches on his wife's estates in Kent were laid under interdict for unlicensed preaching. In the convocation which met in March 1413, shortly before the death of Henry IV, Oldcastle was at once accused of heresy.
But his friendship with the new King Henry V prevented any decisive action until convincing evidence was found in one of Oldcastle's books, which was discovered in a shop in Paternoster Row, London. The matter was brought before the King, who desired that nothing should be done until he had tried his personal influence. Oldcastle declared his readiness to submit to the king "all his fortune in this world," but was firm in his religious beliefs.
When Oldcastle fled from Windsor Castle to his own castle at Cowling (now Cooling), Henry at last consented to a prosecution. Oldcastle refused to obey the archbishop's repeated citations, and it was only under a Royal Writ that he at last appeared before the ecclesiastical court on September 23.
In a confession of his faith he declared his belief in the sacraments and the necessity of penance and true confession; but to put hope, faith or trust in images was the great sin of idolatry. But he would not assent to the orthodox doctrine of the sacrament as stated by the Bishops, nor admit the necessity of confession to a priest. On September 25 he was convicted as a heretic.
King Henry V was still anxious to find a way of escape for his old comrade, and granted a respite of forty days. Before that time had expired, Oldcastle escaped from the Tower by the help of one William Fisher, a parchmentmaker of Smithfield (HT Riley, Memorials of London, 641).
Oldcastle now put himself at the head of a wide-spread Lollard conspiracy, which assumed a definite political character. The plan was to seize the King and his brothers during a Twelfth-night mumming at Eltham, and perhaps, as was alleged, to establish some sort of commonwealth. King Henry, forewarned of their intention, removed to London, and when the Lollards assembled in force in St Giles's Fields on January 10 they were easily dispersed.
Oldcastle himself escaped into deepest northwest Herefordshire, and for nearly four years avoided capture.
Apparently he was privy to the Southampton Plot in July 1415, when he stirred some movement in the Welsh Marches. On the failure of the scheme he went again into hiding. Oldcastle was no doubt the instigator of the abortive Lollard plots of 1416, and appears to have intrigued with the Scots also.
But at last his hiding-place was discovered and in November 1417 he was captured by the Lord Charlton of Powys. Some historians used to believe he was captured in the upland Olchon Valley of western Herefordshire adjacent to the Black Mountains, Wales, not far from the village of Oldcastle itself in his family's old heartlands. Oldcastle who was "sore wounded ere he would be taken," was brought to London in a horse-litter. Modern historians believe that he was hiding with some Lollard friends at a glade on Pant-mawr farm in Broniarth, in Wales called ‘Cobham's Garden.’ The principal agents in the capture were four of the tenants of Lord Charlton of Powys, Ieuan and Sir Gruffudd Vychan, sons of Gruffudd ap Ieuan, being two of them. The reward for his capture was awarded to Lord Charlton of Powys, but he died before receiving it, though a portion was paid to his widow in 1422.
On the 14th of December he was formally condemned, on the record of his previous conviction, and that same day was hanged in St Giles's Fields, and burnt "gallows and all." It is not clear that he was burnt alive.
Oldcastle died a martyr. His unpopular opinions and early friendship with Henry V created a traditional scandal which long continued. In the old play The Famous Victories of Henry V, written before 1588, Oldcastle figures as the Prince's boon companion. When Shakespeare adapted that play in Henry IV, Part 1 and Henry IV, Part 2, Oldcastle still appeared; but when the play was printed in 1598 Falstaff's name was substituted, in deference, as it is said, to the then Lord Cobham. Though the fat knight still remains "my old lad of the Castle," the stage character has nothing to do with the Lollard leader. In 1599 a further play, Sir John Oldcastle, presented Oldcastle in a more kindly light.
The record of Oldcastle's trial is printed in Fasciculi Zizaniorum (Rolls series) and in David Wilkins's Concilia, iii. 351–357. The chief contemporary notices of his later career are given in Gesta Henrici Quinti (Eng. Hist. Soc.) and in Walsingham's Historia Anglicana. There have been many lives of Oldcastle, mainly based on The Actes and Monuments of John Foxe, who in his turn followed the Briefe Chronycle of John Bale, first published in 1544.
For notes on Oldcastle's early career, consult James Hamilton Wylie, History of England under Henry IV. For literary history see the Introductions to Richard James's Iter Lancastrense (Chetham Society, 1845) and to Grosart's edition of the Poems of Richard James (1880). See also W. Barske, Oldcastle-Falstaff in der englischen Literatur bis zu Shakespeare (Palaestra, 1. Berlin, 1905).
Chance to Make a Play for the Home of Falstaff; Old Castle Farm Is Part of an Estate That Belonged to John Oldcastle, the Man Rumoured to Have Been the Inspiration for Shakespeare's Famous Character of Falstaff, Writes Alison Jones
Jun 16, 2011; Byline: Alison Jones The estate that belonged to a man who is one of the contenders for being the inspiration behind the famous...