Life
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 Almeley 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.
Oldcastle represented Herefordshire as a "knight of the shire" in the parliament of 1404, later serving as a justice of the peace, and was High Sheriff of Herefordshire in 1406–07. His grandfather, also Sir John Oldcastle, was Herefordshire's MP during the latter part of the reign of King Richard II.
In 1408 he married Joan Oldcastle, 4th Baroness Cobham, 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 Oldcastle 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.
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