Oliver de Bordeaux was one of a number of Gascon gentlemen who had found employment under the English kings since their country had become so closely associated with his home province after the marriage of Henry II to Eleanor of Aquitaine in 1152. He was a wise and able man who belonged to the great family which, having once governed the capital of Aquitaine, retained its name as that of the House. His father's branch of the family apparently settled in Morlas in the time of King Henry III. Oliver probably first arrived at Court of King Edward I as a very young man. By 1310, he had entered the service of King Edward II as a valet. He was a firm favourite of the King, though, unlike his fellow Gascon, Piers Gaveston, there is no evidence to indicate that he was one of Edward's lovers. However, the King certainly heaped land and other favours upon young Oliver.
In 1308, Edward gave lands in Old Windsor to him, rent free, and many similar grants followed. In 1310, Oliver received, for himself and his heirs, subject to rendering a lance at the Exchequer annually and doing the customary services, all the estates in Windsor and Eton of which John of London and Roger de Mowbray had enfeoffed the King and, in 1312, all the Crown lands at Old Windsor, free of any rent. two years later, he was succeeded in his position as King's Valet by his fellow Gascon, John Brocas. The two were to be close friends and neighbours for the rest of Oliver's life. Nothing seemed too good for De Bordeaux and, in 1317, Foliejon Park and the adjacent Hyremere, both in Winkfield, were added to his possessions, to be held by the service of a rose at Midsummer, should it be demanded. These properties, with all the goods and chattels on them, the King had recently purchased from the Bishop of Bath and Wells, John Drokensford, for £1,000. Difficulties arose about some of Oliver's grants, and they were revoked by Parliament, but finally confirmed on the condition that his heirs paid the usual rents.
The favourite became Constable of Windsor Castle on 6 October, 1319, for a few months only. About this time, he obtained additional land at Old Windsor from Roger the Palmer and his wife, Beatrice. It consisted of 30 acres held directly of the King, and 40 more held of the manor of Old Windsor, "which is of the ancient demesne of the Crown." Oliver was allowed to retain possession, though the transfer had been effected without the necessary Royal sanction. By 1324, he had been appointed Constable of Guildford Castle, a post for which (with only a brief break) he paid the King an annual rent of thirty marks (£20) until he was succeeded by his friend, John Brocas, in 1337. Both men seem to have managed to skilfully steer their way through the troubled times of Edward II’s imprisonment, his assassination and the government of Queen Isabella and her lover, Mortimer. During this period, both Oliver and John kept their heads down. However, very soon after the young Edward III took personal control of his kingdom in 1330, both returned to favour and Oliver was confirmed in his various possessions.
After the death of Sir William Trussell, the proto-Speaker of the House of Commons, in 1346, Oliver married his widow, Matilda, a daughter of Sir Warin Mainwaring of Kibblestone (Staffordshire) & Wormington (Cheshire) and they lived together at Foliejon. They had no children of themselves and decided to secure the succession of their lands to William Trussell Junior, the Constable of Odiham Castle and Matilda's second son by her first marriage. In order to do so, they made a fictitious grant of most of their Old Windsor, Windsor and Eton estates to Matthew, Vicar of Old Windsor. He, in return, regranted them to Oliver and Matilda, and to the heirs of their bodies. These failing, they were to go to William Trussell and his heirs. The arrangement affected only such properties as were held of the King, ie. three messuages, 360 acres of arable, 40 of meadow, 80 of pasture, 10 of woodland, and rents amounting to £14 a year. It had nothing to do with those held in Windsor held of Thomas Uppenore, or in Eton from the Abbess of Burnham. The Old Windsor estates referred to, apparently, did not include Wychemere, adjoining the Great Park. This area seems to have consisted of forest purprestures acquired by Oliver, out of which he formed a separate manor and built a moated house at Bear's Rails.
With the institution of the Order of the Garter in 1348, Edward III's decided to create a fitting home for them by almost completely rebuilding his castle at Windsor – as apparently suggested by his prisoner there, King David II of Scots. The then constable, Thomas Foxley, requested some help in overseeing the construction works and, in 1351, the King commissioned Oliver, as well as Sir John Brocas, to "survey the workmen and their work, to encourage such as did their duty, but to compel those who were slothful". Four years later, however, the War had restarted and Sir John was called abroad once more. William of Wykeham was there architect and he took on the second commission to complete the work when the others moved on in 1356, Oliver into retirement.
King Edward had had an eye on De Bordeaux's extensive holdings so near Windsor Castle as early as 1345, when the merits of taking some of them into the Great Park were discussed in Parliament. Nothing more was done, however, until Oliver was an old man. On 2nd January 1359, his heir, William Trussell, agreed to accept the manor of Eton Hastings, in North Berkshire instead. Oliver was to receive £76.12s.10½d per annum from his former possessions for the rest of his life, and William was to pay the King £50 annually for Eton Hastings till his step-father's death which is believed to have occurred soon afterwards.
Partly edited from TE Hardwood's 'Windsor Old & New' (1929)
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