Sir John was born in around 1378 in Herefordshire, to Sir Richard Oldcastle, and due to the wealth of his parents gained an excellent education. Many people will know of Sir John from the works of Shakespeare, who based Sir John Falstaff in King Henry IV upon him. He was actually better known generally for being a leader of the Lollards and a supporter of Wycliffe, his home in the village of Almeley, North Herefordshire, being a staunch Lollard area, and he was thought of as “The good Lord Cobham”.

The Lollardens

At this time, the Church was rich and powerful, but many people thought that it had lost its way, and they wanted to go back to the simple values without all the pomp and ceremony. Earlier, a group of men had founded a semi monastic community in Antwerp, devoted almost entirely to caring for the very ill or dying – naturally, much of their time was spent at funerals and crooning dirges; the German word for this was Lollen, and it followed that these men became the Lollardens. They had the backing of the common people but were persecuted by the clergy in both Holland and Germany. John de Wycliffe decried the Pope’s claim to be in charge of man’s conscience, publicly saying that it was blasphemous, and he took the Lollardens under his wing. Later, Wycliffe translated the Latin Bible into English so that everyone could understand what was written without having to rely on the clergy with their own twist on things.

Sir John Oldcastle and the Catholics

In 1401, Sir John Oldcastle was sent to take charge of the castle at Builth, following which we took 40 lancers and 120 bowmen to help out at Kidwelly Castle in Carmarthenshire. He was Herefordshire’s Knight of the Shire and sat in the parliament which opened in January 1404, but later that year returned to Hay on Wye in Herefordshire to take charge of the castle there. He was a member of a commission who were supposed to stop arms and provisions from reaching the rebels in Wales, but this was no easy task! However, during this period he became a personal friend of Henry the Prince of Wales. In 1406 he was made Sheriff of Herefordshire, and a couple of years later he married Joan from Kent, the heiress of John 3rd Lord Cobham……Sir John was then created Lord Cobham. By this time, the Catholics were becoming rather concerned with Sir John and his support of the Lollardens, and their concern deepened when in 1410 he got through a law which stated that arrested heretics must be imprisoned by the State and not the Catholic Church. Sir John set up a school in Kent for preachers, and gifted them parishes…….making himself even more unpopular with the Catholics.

In 1411, Prince Henry sent an army under the Earl of Arundel to assist the Duke of Burgundy, and Sir John Oldcastle went as one of the Commanders…… was not a large force, but they managed to prevail against France, and following this victory Sir John’s friendship with the Prince deepened further.

Sir John Oldcastle and Henry IV

In 1413, evidence of a heretical nature began to mount up against Sir John – many of Wycliffe’s belongings had been seized and destroyed, and whilst searching through his belongings several of Sir John’s books were discovered. Henry IV had just died, and King Henry V was reportedly disgusted by the contents of these books, whilst the Archbishop Thomas Arundel and other Bishops present attacked Sir John for maintaining Lollard preachers and their beliefs. Henry was very torn because of his deep friendship with Sir John, and asked the Archbishop for time so that he could try to persuade Sir John of the error of his ways. He failed, and indeed eventually Sir John became so angry that he left the King without asking permission and stormed off to Cowling Castle in Kent.

Sir John Oldcastle is convicted as a heretic

The Archbishop duly sent a summons to Cowling, which was refused by Sir John, and it was eventually stuck to the door of Rochester Cathedral – declaring that he must appear at Leeds Castle. Sir John took no notice, and was therefore excommunicated, with a further writ being sent which told him that he must give good reason as to why he should not be condemned as a heretic. Sir John refused to change his views, and his offer of a signed confession of faith to the King was rejected, along with requests to be tried by knights, or even a trial by single combat. He was eventually arrested under a Royal Writ, and at his trial was offered forgiveness and freedom if he renounced his beliefs. He refused and was convicted as a heretic, but the King was so desperate to try to help his friend that he was granted a 40 day stay of execution, and was put in the Tower of London. From here, he quickly escaped – although how remains rather a mystery. Perhaps a record of a trial some three years later on 4th October 1416, concerning a certain William Parchmyner (a Lollard bookseller) sheds some light? He was taken for trial at Newgate, and was charged, along with other unknown traitors, of breaking into the Tower and releasing Sir John Oldcastle, and then harbouring Sir John in his own house in Smithfield until the planned assembly of Lollards in St. Giles Fields as mentioned below. Parchmyner pleaded not guilty, but was quickly convicted of treason and executed.

Sir John Oldcastle’s escape, capture and death

Sir John reportedly then plotted to have the King, and many others, killed so that he himself could become Regent, and a Lollard assembly was arranged for 10th January at St. Giles Fields just outside London. The King was warned, and he closed the City gates then captured and killed the ring leaders the next day. Sir John himself managed to escape and hid in London before fleeing to Herefordshire where he evaded capture for a further four years, even though there was a reward of 1000 marks on his head. He attempted a rebellion when the King went to France, but failed and he was finally discovered in Broniarth in November 1417 – after a fierce fight he was badly wounded and captured, then taken to London on a horse litter. Parliament once again declaring him a heretic he was condemned to death and on 14th December 1417 was bound in chains, hung and burnt – history is unclear as to whether he was still alive when the fire was lit.