Early Career
In 1429, Waynflete became headmaster of Winchester College, a position which he held until 1441.
During this time, he was appointed by Bishop Beaufort to the mastership of St Mary Magdalen's Hospital, a leper hospital on St Giles Hill, just outside the city of Winchester. The first recorded headmaster after the foundation of the college, John Melton, had been presented by Wykeham to the mastership of this hospital in 1393 shortly before his retirement.
On 3 July 1441 Henry VI went for a weekend visit to Winchester College to see the school for himself. Here he seems to have been so much impressed with Waynflete, that by the autumn, Waynflete had ceased to be headmaster of Winchester. In October he appears dining in the hall there as a guest, and at Christmas 1442 he received a royal livery, five yards of violet cloth, as provost of Eton.
Under the influence of Archbishop Chicheley, who had himself founded two colleges in imitation of Wykeham, and Thomas Bekynton, king's secretary and privy seal, and other Wykehamists, Henry VI, on 11 October 1440, founded, in imitation of Winchester College, a college in the parish church of Eton by Windsor not far from our birthplace, called the King's College of the Blessed Mary of Eton by Windsor, as a sort of first-fruits of his taking the government on himself. The college was to consist of a provost, 10 priests, 6 choristers, 25 poor and needy scholars, 25 almsmen and a magister informator to teach gratis the scholars and all others coming from any part of England to learn grammar. On 5 March 1440–1441, the king endowed the college out of alien priories with some £500 a year, almost exactly the amount of the original endowment of Winchester.
Though reckoned first headmaster of Eton, there is no definite evidence that he was. The school building was not begun till May 1442 (V.C.H., Bucks, ii. 154). William Westbury, who left New College, transferring himself to the kings service, in May 1442, and appears in the first extant Eton Audit Roll 1444–1445 as headmaster, was probably such from May 1442. If Waynflete was headmaster from October 1441 to May 1442, his duties must have been little more than nominal. As provost, Waynflete procured the exemption of the college from archidiaconal authority on 2 May, and made the contract for completion of the carpenter's work of the eastern side of the quadrangle on 30 November 1443.
On 21 December 1443 he was sworn to the statutes by Bishop Bekynton and the earl of Suffolk, the king's commissioners, and himself administered the oath to the other members of the foundation, then only five fellows and eleven scholars over fifteen years of age. He is credited with having taken half the scholars and fellows of Winchester to Eton to start the school there. In fact, five scholars and perhaps one commoner left Winchester for Eton in 1443, probably in July, just before the election. For three of them were admitted scholars of King's College, Cambridge, on 19 July, that college, by its second charter of 10 July 1443 having been placed in the same relation to Eton that New College bore to Winchester; i.e. it was to be recruited entirely from Eton.
The chief part of Waynflete's duties as provost was the financing and completion of the buildings and establishment. The number of scholars was largely increased by an election of 25 new ones on 26 September 1444, the income being, then £946, of which the king contributed £120 and Waynflete £18, or more than half his stipend of 30 a year. The full number of 70 scholars was not filled up till Waynflete's last year as provost, 1446–1447 (Eton Audit Roll).
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