Sir John Oldcastle was born in Almeley (Elm Meadow), Herefordshire in 1370, the son of Sir Richard Oldcastle.
The first time he appears in history is when he served in the expedition to Scotland in 1400 when he was helping the Percies to sort them out.
In 1401 he was put in charge of Builth Castle when the Welsh rose up under Owen Glendower when they proclaimed him 'Prince of Wales'. Oldcastle served in all the Welsh campaigns, such as in 1403 when Henry Prince of Wales defeated the combined forces of Glendower and Hotspur at Shrewsbury. This earned Richard the frienship and the respect of young Henry, and he following year Richard represented Herefordshire in Parliament.
In 1408 he married Joan, heiress of Cobham in Kent, and afterwards Richard was summoned to Parliament as Lord Cobham. In 1411, being someone in whom the Prince had great trust and regard, Richard was sent to France holding a high command in the expedition.
The Lollards, the folowers of John Wyclif, were a group of proto-Protestants that prefigured the Reformation by over a hundred years. For example they denied transubstantiation, and believed that the Bible ought to be made accessible to everyone by translating it from Latin into English, which was done in the 1390's.
For a while the Lollards enjoyed some royal protection because Richard II's wife, Anne of Bohemia was sympathetic. However under Henry IV, in 1401, the statute de heritico comburendo was introduced which made deemed heresies such as Lollardry punishable by burning to death, and in 1407 the Lollard Bible was banned.
Richard was one of the many Herefordian Lollards and the churches on his wife's estates preached Lollardry from their pulpits.
For this unlicensed preaching, the churches on those Kent estates were laid under interdict. In March 1413 there was a convocation just before Henry IV died whereby Oldcastle was accused of heresy, but his friendship with the new king, Henry V presented any moves being made against him until they found in a shop in Paternoster Row some evidence in one of Richard's books. Being brought before the monarch, Oldcastle declared that he was ready to submit to the king "all his fortune in this world" but was steadfast in his spiritual beliefs.
However, after Richard had fled from Windsor to Cowling, Henry V, at last decided to allow him to be prosecuted. Oldcastle would not obey the Archbishops citations so was dragged before the ecclesiatical court on September 23rd 1413. In front of these churchmen, whe declared his belief in the sacraments (though not those as stated by the bishops) and the need to perform penance but said that it would be idolatry to put faith or trust in images. , and he did not see why he had to confess to a priest. Two days later he was convicted as a heretic and hence sentenced to be burnt to death.
Henry who still liked and cared about his old Herefordshire pal, granted him a respite of forty days. During that time Richard escaped from the Tower of London with the help of a man called William Fisher who was a parchmentmaker of Smithfield.
Oldcastle now put himself in charge of a wide-spread Lollard conspiracy to seize power. The cunning plan was to seize king Harry & his brothers whilst they were doing a bit of mumming during Twelfth night at Eltham Palace, maybe with the aim to establish come sort of commonwealth. However, someone tipped Henry off, so he left Eltham for London, and the Lollards who had gathered en masse in St Gile's Fields on January 10th were scattered without much difficulty.
Between Wigmore and Lingen lies a stretch of rough and then unfrequented country known as Deerfold Forest, where in the early part of the 15th century, the much-persecuted Lollards found a refuge from their oppressors. For example, one of the earliest preachers who lived there was a certain William Swynderly.
Richard managed to get away from St Gile's and fled back to Herefordshire, where by lying low, he stayed on the run for four years. It is believed that he was given sanctuary in Chapel-house Farm, Lingen. By the way, near to Chapel-house Farm was a specimen of that botanical curiosity, the mistletoe-oak, of Druidical fame. The evidence is that he was privy to the Scrope & Cambridge Plot in July 1415 when he roused some movement in the Marches. When this plot didn't come to fruition, Richard went on the run again. It is without doubt that Oldcastle was the ringleader of the abortive Lollard plots of 1416, and it looks like he was in intrigue with the Scottish.
Near to the Black Mountains in Herefordshire lies the Vale of Olchon. Half way up this valley stands Olchon Court, a small stone farmhouse which keeps its secrets for those who enter it or know its history. In the deeds of the house the old name is given as Court Walter, from the time when it was one of the manor-houses of Walter Brut, the famous Lollard. It was also once known as Court Nicholas, and may thus have been linked with that other great figure of the times, Nicholas Hereford, one-time Lollard and friend of Brut. All this borderland was strong Lollard country, and tradition says it was here, in Walter Brut's house, that Sir John Oldcastle, spent much of his time in hiding after his escape from the Tower of London. In the dining room are the remains of a secret chamber beside the fire-place where he and others may have often hidden while the house was being searched, and upstairs is the window from which he jumped when his enemies surprised him just before his betrayal.
The miseries caused by the Black Death led in their turn to the turmoil in the spiritual life of the realm. Under Richard II the Lollards had been protected, since his wife, the beloved Anne of Bohemia, friend of the great reformer John Huss, was well disposed to them. It it to no honour to the then vicar of Kinnersley that he gave the information as to Sir John's whereabouts. But the whole county had so many Lollard sympathisers that perhaps he feared for his own position. For it seems to have been well peppered with those who either held Lollard beliefs, or else strongly sympathized with those that did. The Whitneys, of the villatge of the same name near Hay, supported Wyckliffe's doctrines, and Sir Robert Whitney's second wife, Joan, was Thomas Oldcastle's daughter. His sister, Lady Peryn Clanbowe, left in her will; 'a boke of English cleped 'A Pore Caytife' (A Book of English called 'A Poor Caitiff') which was a work of very strongly pronounced Lollard teaching. Another Herefordshire family were the Burleys. Sir John Burley, friend of the poet Chaucer, together with his brother, Sir Simon, were amongst the first of the original Knights of the Garter, and Sir Simon was selected to escort Anne of Bohemia when she came to England to marry Richard II. But even her friendship could not save him from the ill-will of the Duke of Gloucester, who was virtually in charge of the kingdom. Simon was 'appealed of malversation and other acts of treason', and Wat Tyler's insurrection was laid to his charge, though historical evidence indicates that this was a trumped up charge and would have been unlikely in the extreme. On her knees, Queen Anne besought Gloucester for her friend's life, pleading for him with tears but to no avail, and Sir Simon, scholar, courtier, friend of Froissart, and most gallant knight was marched to Tower Hill on a summer's day in 1388 his hands tied behind his back, and there life any common felon was beheaded. Walter Brut, Nicholas de Hereford, and William Swynderby, were all staunch Lollards and sought to spread their beliefs throughout the county, though Nicholas de Hereford, after a spell in a prison in Rome and London, seems to have submitted to the Church, for in 1391 he was appointed Chancellor of Hereford Cathedral, and this strange and sudden reversal of his fortunes was followed in 1397 with being appointed Treasurer. He was greatly disliked by his former Lollard colleagues, one of them calling him 'master of the Nicholaitanes' in a letter. Certainly at the trial of Walter Brut in 1393, he was one of the most relentless of the interrogators.
In November 1417, Oldcastle was at last found out and captured by the Lord Charlton of Powis. Richard who was "sore wounded ere he would be taken" was delivered to the capital in a horse-litter. On December 14th he was officiallly condemned for his previous conviction, and later that day was strung up at the gallows in St Giles' Fields, and burnt "gallows and all", though it is not certain whether or not he was actually burnt alive as de heretico comburendo would have stipulated.
Because of his jolly character, Richard Oldcastle was the model for Falstaff in Shakespeare's play, Henry IV