John was the only son of Sir Thomas Golafre (d. 1378) of Radley Manor in Berkshire, by his wife, Margaret, the daughter of Thomas Foxley of Bray, Constable of Windsor Castle. He was the nephew of Sir John Brocas, the Master of the King's Horse. As his father was a younger son, he, at first, inherited only modest estates in mid-Berkshire but, upon his Uncle John's death in 1379, he was given considerably more, centred on Fyfield Manor. Through his bastard cousin, also Sir John Golafre who was King Richard II's closest friend, he also obtained a position as a squire at the Royal Court in 1395. Unfortunately, his cousin died the following year, but his widow, Philippa, remarried to the King's cousin, Edmund, the 2nd Duke of York, so John was able to retain close connections with the Royal family.
In 1397, after the King's revenge had been acted out on the Lords Appellant who had tried to curtail his power, John was appointed Sheriff of Berkshire and Oxfordshire. He was elected Knight of the Shire (MP) for Oxfordshire in the same year and, subsequently, became one of the commissioners exercising parliamentary power after Parliament's dissolution. During the troubles of 1399, John initially continued to support King Richard and he was thrown in prison when the monarch was captured by his cousin, Henry Bolingbroke. However, when he took the Throne as King Henry IV, John found himself obliged to accept the situation and he was allowed to remain sheriff until a successor was found. His various Royal annuities were quickly re-confirmed, though he was dropped from the Oxfordshire Commission of Peace.
John was elected Knight of the Shire (MP) for Berkshire in 1401, a position he held twelve times over the next thirty years. That same year, the Earl of Suffolk's niece, Elizabeth, the daughter of Sir Edmund de la Pole of Boarstall Castle in Buckinghamshire, co-heiress of her mother, Elizabeth Handlo, and widow of Sir Ingram Bruyn of South Ockendon in Essex, became John's wife. Her sister, Catherine, was married to Robert James of of Anesty's Manor & Rush Court in Clapcot. It was the first of three very lucrative marriages for John, although this one did not last long. Elizabeth died, possibly in childbirth, in 1403. The following year, he married Nichola, the daughter & heiress of Thomas Devenish of Greatham in Hampshire and widow of John Englefield (d. 1403) of Englefield House. He was also appointed Justice of the Peace for Berkshire that year, and continued so for most of his life, as well as being made Sheriff of Berkshire and Oxfordshire again (which he later held twice more). By 1408, John had become a close associate of perhaps the most influential man in the local area, Thomas Chaucer, the Constable of Wallingford Castle and sometime Speaker of the House of Commons, as well as his future son-in-law, the Earl of Salisbury. They were involved in numerous land deals together and Chaucer appointed Golafre as Controller and Overseer of Woodstock Palace in Oxfordshire. By 1416, John had risen, not only in the estimations of Royalty and nobility, but also in those of all local people, for he was one of the members of the Fraternity of the Holy Cross who made a large contribution to the building of the first Abingdon Bridge. This greatly boosted trade in the town as merchants no longer had to cross the Thames at Wallingford.
During Henry V's second expedition to France, when he was trying to claim the French Throne, John was amongst his army and was appointed Receiver-General of the Duchy of Normandy and all occupied France in 1418. He relinquished the post in June 1419 but remained in France until the Autumn. By Spring the next year, John was back in England, running the manor of Bradfield during the minority of the Royal ward, Edward Langford. Land transactions with the great and the good continued throughout the 1420s and 30s, including with Chaucer's daughter, Alice, and her third husband, William de la Pole, Earl of Suffolk, a cousin of John's first wife. It was through him that he obtained the custody of Cornbury Park in Oxfordshire. The continuing De la Pole connection soon led, in 1434, to John's third marriage to Margaret, daughter of Sir John Heveningham and widow of Sir Walter de la Pole of Dernford at Sawston in Cambridgeshire who was his first wife's half-brother. In old age, John was again one of chief members of the Fraternity of the Holy Cross in Abingdon who funded public works, this time the erection of the famous Market Cross in the town in 1438. It is said to have been designed by his friend, Chaucer. Golafre died four years later, on 23rd February 1442, and was buried under a fine monument in Fyfield Church, featuring both his armoured effigy and a rotting cadaver.
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