Of all the rather memorable personalities and (borderline) incestuous pairings during the Wars of the Roses, the one that I find the strangest is without a doubt Jasper Tudor and Katherine Woodville. They literally make zero sense to the point that I honestly sometimes forget about them. And yet! They existed.

For the uninitiated, Jasper Tudor was a younger half-brother of Henry VI. The two shared a mother, Katherine of Valois, though Henry was a result of her first marriage of Henry V and Jasper was the product of her secret second marriage to Owen Tudor, a Welshman far below her station. Jasper is generally presumed to be the second son of that marriage, born about a year after his elder brother, Edmund. Katherine died in early 1437 when Jasper was still a child. He and Edmund spent the next few years at Barking Abbey under the protection of William de la Pole, Earl of Suffolk (later duke) via his sister, who was Abbess.

In the early 1440s, Henry brought his brothers out from the religious house and funded a secular education. In the early 1450s he brought them to court, invested them in the peerage and relied on them as trusted members of his council. Unfortunately for both young men, England was veering right into civil war and it wasn’t a particularly fun time to be at the epicenter of political power. Jasper, now the Earl of Pembroke, served for a few years as a mediator between Henry and his rival, the Duke of York, before finally casting his lot in whole-heartedly as a member of the House of Lancaster.

Edmund, meanwhile, married the royal-adjacent heiress Lady Margaret Beaufort and quickly died, but not before fathering a son, Henry. Jasper quickly took his sister-in-law and nephew under his wing, arranging a speedy remarriage for Margaret with a son of the Duke of Buckingham. Throughout the 1460s, once Henry VI was deposed, Jasper worked tirelessly to topple the Yorkist regime and reinstate his half-brother. He was a constant nuisance to Edward IV on the Welsh border and was pivotal to the Lancastrian resurrection of 1470-1471. Reunited with Margaret and Henry Tudor, he was there for the legendary meeting of the two Henrys, though it’s unknown what exactly went down.

When Edward IV took back the throne in the spring of 1471, executing Henry VI and his son, Prince Edward, Jasper spirited Henry Tudor out of the country. Headed for France (Jasper was first cousins with Louis XI thanks to his mother), the two ended up in Brittany at the court of Francis II. There they essentially lived as honored hostages while Francis dangled them as bait before Edward IV and then Richard III, though he never gave them up to the English. Eventually Henry made it to France where the government of Louis XI’s son, Charles VIII, helped finance his 1485 invasion, toppling Richard III and establishing the House of Tudor.

Katherine’s trajectory was understandably a bit different. Most importantly, though, she was as Yorkist as Jasper was Lancastrian. Born in 1458, she was considerably younger than her future husband (25+ years). When Edward IV ascended the throne 1461, her parents, Richard Woodville, Earl Rivers and Jacquetta of Luxembourg, Duchess of Bedford, switched sides to the pledge allegiance to the House of York. Three years later, Katherine’s elder sister, Elizabeth, married Edward IV, to the great surprise of Western Europe, not to mention the King’s court and government.

Only a child when this all went down, Katherine was raised in her sister’s household amidst considerable luxury. A lofty marriage was arranged for her within months of her sister’s marriage to Henry Stafford, Duke of Buckingham. (Usually I refer to people by their Christian names, but because of all the Henrys, I’ll use his title). Buckingham was only about four years older than Katherine and both were well-below the canonical age of consent. He assumed his title after his grandfather’s death in 1460 (his father had already died) and became a ward of the King.

There has always been whispering that Buckingham was horrified by his marriage to a Woodville, believing his wife to be far too common for him. There’s no contemporary evidence to support this notion and it likely stems from the Yorkist political split that opened up a couple decades later. While it’s true that Katherine wouldn’t have been a candidate for Buckingham prior to Elizabeth’s marriage, the fact remained that she was the Queen’s sister and on those ground alone, it wasn’t a bad marriage for Buckingham. And given his age at the time (around 10 or 11), it’s even less likely that any opinion was recorded.

It’s unclear when Buckingham and Katherine consummated their marriage, but she conceived her first child in the summer of 1477 when she was 18 or 19 years of age. Her son, Edward, was born on February 3, 1478 and was followed by three more children: Elizabeth (b. 1479), Henry (b. 1480/1) and Anne (b. 1483).

1483 was a bit of seismic year for Katherine, to put it mildly. Edward IV died, her nephew, Edward V, ascended the throne, and was promptly set aside by Richard III. Elizabeth and her other children fled for sanctuary within Westminster Abbey. The catch was that Buckingham was Richard’s closest advisor in all of this, thus putting Katherine on the opposing side of her sister. Indeed, it was Richard and Buckingham who implemented a rationalization for the new king’s deposition that branded Edward and Elizabeth’s marriage illegal and their children bastards. It’s unclear where Katherine landed on all of this, but given her later good standing in the Tudor court, it’s fair to say that she wasn’t actively involved in her husband’s actions.

Buckingham eventually split from Richard (more on that some other time) and aligned himself with Elizabeth and Margaret Beaufort as they plotted to marry their children, Elizabeth of York and Henry Tudor. What was in this for Buckingham? Debatable. But it’s not out of the realm of possibility that Katherine played some role in facilitating a rapprochement between her husband and sister.

Unfortunately, Richard found out about the hatched rebellion and Buckingham was quickly arrested and put to death on November 2, 1483.

Katherine plead for leniency before Richard on behalf of herself and her children, a plan which somewhat worked, though her financial situation wasn’t ideal and her eldest son remained in Richard’s custody. By early 1484, Elizabeth and her daughters had returned to court and all parties remained uneasily free and loyal until Henry Tudor bested Richard at the Battle of Bosworth in August 1485.

But strangely, before Henry Tudor even followed through on his promise to marry Elizabeth of York – thus uniting the two houses – Henry arranged for the marriage of his uncle to Elizabeth’s aunt. On November 7, 1485, Jasper and Katherine were married in London, ensuring Katherine a place of security in the new reign.

What’s odd about that is that there is some angst about what the relationship between Elizabeth Woodville and the Tudors was – some even argue that she was instrumental in a 1487 plot to depose Henry that failed at the Battle of Stoke Field. Yet, Henry chose a Woodville for his beloved and loyal uncle, not a Plantagenet Yorkist.

Some of that may be fairly uninteresting. Regardless of anything, Katherine was also Elizabeth of York’s aunt and Henry Tudor was due to marry her in January 1486. The Woovilles were also beautiful women and Katherine, still only 27, was young and fertile enough to be physically attractive and provide the never married, much older Jasper with an heir.

Whatever the motivation, the marriage remained childless. Katherine mainly stayed away from court despite her high rank (Jasper was made Duke of Bedford after Henry’s accession, making Katherine a duchess once more), residing at Thornbury Castle in Gloucestershire. We have almost no information about the marriage itself, including the relationship between the two. One can assume, though, that it was certainly not a love match. Jasper died on December 21, 1495 and Katherine only receives a brief mention in his will. The lack of honor in Jasper’s will combined with the fact that they were childless despite neither being infertile (Jasper had illegitimate children) indicates the marriage may have been less than warm.

Katherine immediately (within weeks of Jasper’s death) married for a third time to Richard Wingfield, presumably for love. They had no children and Katherine died on May 18, 1497 at the age of 38 or 39.

So, why is this marriage so strange? Well, for a marriage that lasted 10 years there’s almost zero mention of them in the history of Henry VII’s court despite their familial relationship to the king and queen. Both are worthy of mentions in the dynastic history of the Wars of the Roses, yet separate and apart from one another. They came from opposing ends of the political spectrum, married one another and then dissolved into, well, nothing. It’s a strange footnote to both of their lives, but a substantial one at that. Barring discoveries, the motivation and reality of this marriage has been lost to history.