#william herbert

Those two dates are relevant to the Yorkist establishment (hold this thought). I think it's possible those three men first met Elizabeth of York as she fled with her mother and siblings in 1470 to the Tower and then to Westminster Abbey, or they might have met her in 1471 when Edward IV returned and rescued his family from sanctuary. I don't know exactly what kind of ceremonies were held after Edward's triumph over the Lancastrians but it's possible Elizabeth was present on those occasions.

Some of the other witnesses said they knew Henry for sixteen/fifteen years as well — specifically Christopher Urswyck (Margaret Beaufort's confessor) and Sir William Knyvett. It would make the most sense for the majority of people to say they knew Henry since 1470/1, considering Henry Tudor came to London during the readeption of his uncle Henry VI, and would have met the courtiers at that time. But those three people* — the Earl of Nottingham, Sir Richard Croft and Sir William Tyler — said they knew Henry at least since 1466. What was Henry Tudor doing in 1466?

At that time Henry was a 9 year-old in the custody of William Herbert, an important representative of the Yorkist king in Wales described as 'King Edward's master-lock'. It's possible William Berkeley (later Earl of Nottingham), Sir Richard Croft and William Tyler all knew Henry from visiting the Herberts in Rhaglan Castle**, though it's impossible to say if they had any degree of personal friendship with the Herberts. In 1466 there was however an event that was of importance for both the Herberts and Edward IV.

In that year William Herbert married his eldest son and heir to Mary Woodville, the king's sister (in-law) in a ceremony that took place in Windsor Castle, one of the king's residences. It was apparently such a great event a Welsh poet later praised it in one of his poems dedicated to Willaim Herbert:

The foremost king of Britain and its realm / Gave his sister to him / He held a great wedding-feast in Windsor / For this man, in his royalty / A generous feast for our lord who is of our tongue, / May he be seen again as a prince!

This is pure speculation but I ask myself: is it possible William Herbert took his whole family to Windsor, including his ward Henry Tudor, for his son's wedding feast? If so, many Yorkist partisans such as the Earl of Nottingham and Sir Richard Croft would have had the opportunity to meet Henry on that occasion — in turn, Henry would have had the opportunity to at least see King Edward. Of course there's no way to really know that whilst no concrete evidence comes up, but it's fascinating to think Henry might have seen/know Edward IV.

This isn't taking into account, for example, the possibility that Edward IV might have visited William Herbert at Raglan in one of his travels, to which Henry would have seen him as well. A royal visit to Raglan is the only way I can think of that Henry might have seen Elizabeth of York, as she was only merely a few months-old at the time of her aunt's wedding in Windsor, and would not have attended the ceremony. Furthermore, if Henry and Elizabeth had been present on the same occasion/wedding the three witnesses above would have given the same number of years for knowing them both***, which was not the case.

However, I think a royal visit from Edward IV to Raglan is less likely, given it was not documented anywhere, not even in Welsh poetry, and William Herbert was enough of a patron to have this visit documented in that way. So all in all, I think it's very unlikely Henry Tudor ever met Elizabeth of York before 1485, though I think there's a slight chance that he have met Edward IV in 1466. Again, this is all pure speculation, though.

_____________

* It's important to notice that all three were Yorkist partisans: Sir Richard Croft fought at Mortimer’s Cross, Towton and Tewkesbury on Edward IV's side — he and his brother were tutored with or were the one who tutored Edward whilst Earl of March and his brother Edmund in Ludlow*. Apparently the letter Edward and Edmund jointly wrote to their father Richard of York complained about Sir Richard Croft and his brother. The Crofts were neighbours of the Mortimers, which then encompassed Richard of York and his sons. The Battle of Mortimer's Cross took place on Croft soil. Sir Richard's wife Eleanor ran the household of Edward Prince of Wales, Edward IV's son, and his younger brother (also called Richard Croft) was one of Edward's tutors in Ludlow. Henry VII later made Sir Richard Croft his treasurer, and also made him Prince Arthur’s steward in Ludlow later on.

William Berkeley was created Baron Berkeley by Edward IV and became one of his privy councillors in 1482/3. He might have been the same William Berkeley, knight of the Body, who was attainted in Richard III’s Parliament and joined Henry in exile. It would be weird for the act in Parliament not to mention his title, though, since he was created Earl of Nottingham two days after Richard III was declared king. Either William Earl of Nottingham or this other William Berkeley, knight of the Body, hosted Margaret of York when she visited England in 1480.

** It would be really awkward if William Berkeley (later Earl of Nottingham) was intimate enough to visit the Herberts, considering he killed in battle William Herbert's son-in-law, Thomas Talbot, 2nd Baron/Viscount Lisle (Margaret Herbert's husband) after Lisle challenged him to a trial of arms over the Berkeley lands in 1470. Lisle had been Herbert's ward in the same way Henry Tudor had been. His wife Margaret Herbert miscarried a boy shortly after his death. I believe this is the dowager Viscountess of Lisle that Henry granted a financial settlement in 1492.

William Herbert was an ambitious Welshman, and Walter Devereux was a prominent Hertfordshire knight, both dedicated to the House of York.

Facing them, the Lancastrian faction was led by Jasper and Owen Tudor. Jasper, as Earl of Pembroke and half-brother of the king, commanded great influence in southern Wales. His brother Edmund clashed with Devereux in 1456 as York tried to rise in influence in the region. James Butler was with them as Earl of Wiltshire and Ormond. The Butler family was powerful in Ireland and headed the Lancastrian faction in an unstable island where Yorkist influence was prominent. He fought with the Tudors. However, his marriages with the Beauchamp and Beaufort families gave him lands and interests in the Welsh Marches and the West Country, making him a powerful magnate outside of Ireland.

The stakes were high. Edward IV was the only adult Yorkist alive capable of championing the Lancastrians. More locally, Jasper and Owen had a grudge against Deveureux and Herbert, who waged war against their interest in 1456.

The Lancastrians were probably less numerous than the Yorkists, but their aggressive strategy gave them a shot at beating them.

Butler attempted an aggressive encirclement of the left flank, forcing Devereux to retreat. Meanwhile, Pembroke faced the duke of York. Owen's attempt at crushing Herbert and forcing an encirclement could have changed History, but it failed, and his 'battle' began to rout. Herbert's decisive hold allowed a Yorkist victory and the capture and execution of Owen Tudor.

This victory would mean much for the Yorkist. Everyone on the Yorkist side was eventually promoted. Deveureux and Herbert would become lord in 1461, just like Sir Humphrey Stafford, who fought with them. York would become king of England a few months later. The reverse was also true, as Jasper Tudor lost his earldom in favor of the Herberts (1469) and Butler lost his life a few months later and his family lost his earldom of Wiltshire with it. Jasper would regain his lands only after the battle of Bosworth twenty-four years later, in which Walter Deveureux, as lord Ferrers, would die fighting for Richard III.

Sun Dog in the Nuremberg Chronicle.