He was an estate officer and senior councillor to both Henry VII and the king's mother, Margaret Beaufort.

He was a major benefactor to St George's Chapel, Windsor, where some of the building work for which he provided funds can still be seen and identified.

[3] With his younger brother, John, Bray entered the service of Margaret Beaufort during the period of her first marriage to Sir Henry Stafford, acquitting himself sufficiently well to become the couple's receiver-general by 1465.

For example, in 1469 he brought the young Henry Tudor a gift of money from his mother to enable the boy to purchase a bow and arrows.

To this end, he acted jointly with the merchant Avery Cornburgh as under-treasurer of the Exchequer from mid-October 1485; and, on 28 February 1486, he replaced Archbishop Thomas Rotherham as Treasurer, serving until July 1486.

[5] Neither Bray's office of Chancellor of the Duchy, nor the various receiverships, stewardships, custodianship of castles, and the like, to which he was appointed by the king, fully explain his influence.

This spilled over into personal profit, whether such minor gifts as food and drink, or larger rewards of money and appointments to estate office and trusteeship by those seeking his favour.

[18] It would be more accurate to call him a prodigious builder, both on his own behalf, and by funding and assisting friends and projects in which he took an interest.

[21] He contributed to Jesus College in Cambridge[19] and lent his assistance to Bishop Oliver King for building works at Bath Abbey.

[26][27] The hemp-bray was a fairly crude implement used to separate the fibres of hemp from the tough outer coating of the dried stems of the plant, and was an effective pun on Bray's name.

[23] A further ten such images, carved in wood, have recently been added by way of embellishments to the new furniture created by Treske of Thirsk for the Bray Chapel.

[30] In 2017 the Royal Mail issued a commemorative set of postage stamps celebrating Windsor Castle and St George's Chapel in which one of the quartet of stamps showing the Chapel was an illustration of a stone roof boss carved with Bray's initials set within the garter.