Sir Reginald Bray is often mentioned as Margaret Beaufort’s man of business and then as Henry VII’s advisor – a sort of Tudor prime minister and chancellor of the exchequer rolled into one politically astute package. Bray first came to Tudor attention when he was master of the household to Margare Beaufort’s third husband (if you count the childhood proxy marriage and annulment from John de la Pole), Henry Stafford and given that Richard III issued him with a pardon of Lancastrian sympathies. His father is mentioned by Leland as one of Henry VI’s doctors. Indeed Sir Reginald is also mentioned as doctoring Henry. There seem no end to the man’s talents. In the meantime after Sir Henry Stafford’s death, following injuries sustained at the Battle of Barnet in 1471, Bray continued as the steward of Margaret’s household.

Somehow or other Bray often found himself at the centre of things. Whilst Margaret Beaufort was conspiring with the Duke of Buckingham in 1483 it was Bray who carried messages for Buckingham on the advice of his ‘house-guest’ Bishop Morton of Ely who described Bray as “secret, sober and well-witted.” Following Bosworth it was Bray who allegedly retrieved Richard’s crown from a thorn bush so that Lord Stanley could place it on his step-son’s head. It was Bray who told Henry VII during his progress to York in April 1486 that Lord Lovell and the Stafford brothers (Sir Thomas and Humphrey) intended to break out of sanctuary in Colchester. Henry initially didn’t believe him because Bray’s source would not reveal the name of the person who had told him the information. On a later occasion Sir Francis Bacon records that bray paid a bribe of £500 from the king’s privy purse to Sir Robert Clifford to betray Perkin Warbeck.

Bray appears to be something of a polymath since not only did he do finance and spying but also a spot of doctoring and architecture. He had a hand in the design of Henry VII’s chapel at Westminster and also St George’s Chapel Windsor. The image of the Sir Reginald on the left hand side of the picture in this post comes from the Henry VII window at Worcester Cathedral. Sir Reginald was one of the donors.

Sir Reginald reaped the rewards for his service. As well as being made a knight of the Bath he also became a knight of the Garter, was granted the constableship of the castle of the castle of Oakham in Rutland, and was appointed joint chief justice of all the forests south of Trent, and chosen of the privy council. After this he was appointed high-treasurer and chancellor of the duchy of Lancaster. He was also made keeper of the parks of Guildford and Henley, with the manor of Claygate in Ash for life. He was also high steward for the university of Oxford and a member of Parliament.

In Jun 1497 following the Cornish Rebellion and the Battle of Blackheath he was rewarded with more titles. He also landed Lord Audely’s estate in Surrey when the unfortunate lord was found gulty of treason and lost his head.

He was born in Worcester in 1440 and buried in St George’s Windsor in 1503 after a career devoted to the Tudors. Edmund Hall extolled him as “a sage and grave person.”