- "My Order was...surprised at your Cardinal's willingness to help us hunt a monk."
"It is not His Grace of Canterbury's way to show greater mercy to guilty churchmen than guilty laymen. Nor, I assure you, is he an unworldly man. He is entrusted by His Majesty with great secular authority and for good reason; your brethren may trust his reports." - ―Leone Paleologo and Reginald Bray discussing Cardinal Morton's assistance in the Italian Assassins' search for Savonarola, c. early 1490s
Sir Reginald Bray (c. 1440 - 5 August 1503) was an English administrator and statesman. Along with Cardinal John Morton, he was one of the longest-serving and most trusted advisors of King Henry VII of England, under whom he held various offices. He was also an affiliate of the Assassin Brotherhood, serving as a vital go-between for the Order and the king's court.
Bray was born around 1440 in Worcestershire, the second son of John Bray, a surgeon. His father's profession ensured he and his brothers received a better education than most other commoners of their day, and by his 20s, Bray along with one of his brothers was in the service of Margaret Beaufort, Henry Tudor's mother. He often ferried clandestine messages and gifts from his matron to her exiled son. He played an active part in the machinations of Margaret, Henry, and their supporters to dethrone Richard III, and it is believed that the Assassins first established contact with him between 1483 and 1487, during the final phase of the Wars of the Roses.
Having known Henry Tudor since he was a boy, Bray immediately became a trusted fixture of his court when he ascended to the throne as Henry VII in 1485, afforded the rank of Privy Councillor and Chancellor of the Duchy of Lancaster among other honours. Noted for being best at gathering money for the king, he briefly served as Treasurer, and would retain some fiscal responsibilities for the rest of his life. The king's reliance on Bray was such that later historians would compare his function to that of a Prime Minister.
To the Assassins, he acted as their eyes within Henry's government, and in return would often pass on Assassin intelligence about Templar Yorkist activities to the royal court. The main Assassin envoys to Bray were Leone Paleologo di Pesaro (illegitimate half-brother of Byzantine princes Andreas and Manuel Palaiologos), and the Venetian father and son Giovanni and Sebastiano Caboto. Especially during the 1490s, Bray seems to have collaborated closely with the Assassins who shared his interest in preventing Henry's usurpation by Templar-backed Yorkist pretender Perkin Warbeck. It was in part thanks to Assassin intelligence passed to Bray that Sir William Stanley (the king's step-uncle and Chamberlain) was found to be secretly conspiring with Warbeck, and ultimately found guilty of treason and beheaded in 1495. Bray in turn passed on leads from Cardinal Morton's international network of informants to the Italian Assassins that helped them to relocate the fugitive monk Girolamo Savonarola. Bray's contact with the Assassins proved invaluable in other ways too; in 1496 the Caboti formally entered the king's service as explorers, and would conduct an expedition to North America with English backing in 1498.
When Morton died in 1500, Bray began to lean more heavily on his Assassin contacts, deprived of his most eminent and experienced ally at the English court. Through Paleologo and Sebastiano Caboto, he maintained close contact with Italian Assassin leaders Niccolò Machiavelli and Ezio Auditore da Firenze, working with them and their apprentices to snuff out lingering Yorkist dissent.
These efforts attracted the attention of King Henry's Templar Yorkist archrival, Margaret of York, Duchess of Burgundy and sister of Richard III and Edward IV, who had sponsored most if not all the Yorkist plots against Henry VII across his reign. Pinpointing Bray as the Assassin collaborator at Henry's court, and glad of an excuse to rid Henry of the longest-serving and most experienced advisor he had left, Margaret hired a Borgia-trained assassin to kill Bray. He was successful, killing Bray in London on 5 August 1503; Bray was around 63 years old.
However, having been warned some years earlier by Mario Auditore of the fate of his brother Giovanni, Bray seems to have prepared for this eventuality. He'd left the King a sealed letter explaining that should he die suspiciously it would likely be the Duchess' doing, and directing him to reconnect with Paleologo. Henry did so, leading to Margaret's own assassination only a few months later, and thus Bray was avenged.