Cecily of York has always perplexed me. A daughter of one queen and sister to another, she was not only at the epicenter of “Wars of the Roses” drama, but unlike her younger sisters, Anne, Katherine and Bridget, she was old enough to know what was happening. She also came very close to playing a more high-profile role thanks to her betrothal to the future James IV of Scotland, and had her first marriage abruptly annulled when power changed hands in 1485. So, who exactly was this woman?

Cecily was born on March 20, 1469, the third child of King Edward IV and his wife, Elizabeth Woodville. She joined two older sisters, Elizabeth and Mary, making her gender a marked disappointment to a dynasty that desperately needed a male heir. Her father, however, was no Henry VIII and also had the benefit of two able-bodied younger brothers. She was named after her paternal grandmother, the venerable Cecily Neville, Duchess of York and was described at birth as a “very handsome” child.

Her birth year was the beginning of yet another interlude of fighting in the midst of ongoing civil war. Still smarting over the unpopular marriage of Cecily’s parents, Edward IV’s cousin and right-hand man, Richard Neville, Earl of Warwick, launched a rebellion alongside Edward’s younger brother, George, Duke of Clarence. The plot was meant to remove Edward from the throne in favor of George, while Warwick defied his king by marrying George to his eldest daughter, Isabel. Edward spent several weeks under house arrest up north while Queen Elizabeth and their three daughters waited anxiously for the situation to resolve itself. In the end, the public had no desire for power to change hands yet again, Warwick was unable to gain control of the government and Edward was released. (We’ve covered this period many times before, particularly here.)

But despite a brief reconciliation, Warwick and George broke from Edward yet again in 1470. This time Edward was forced into exile, which he sought in Burgundy where his sister, Margaret, was married to Charles, the Duke of Burgundy. Warwick had aligned himself with the House of Lancaster and pledged to restore the deposed Henry VI to the throne alongside his wife, Marguerite of Anjou, and his son, Prince Edward, to whom he wed his younger daughter, Anne.

By October Warwick had opened a government in Henry’s name and England was once more Lancastrian. Queen Elizabeth and her children entered sanctuary in Westminster, and for roughly six months this is how the infant Cecily lived – confined to a few small rooms with her sisters, mother and a handful of servants and visitors. Queen Elizabeth was also heavily pregnant and that November she finally gave birth to a son, christened Edward after his father. By the spring of 1471, Edward defeated the Lancastrians and was restored to his throne. Elizabeth and her children left sanctuary and for the next 12 years there was peace under York.

Cecily was educated alongside her two sisters and there is evidence that their mother played a direct hand in teaching them reading, writing and the other skills they might need as possible queen consorts in foreign courts. All of the girls were literate, and at least the older girls seem to have been taught French alongside English. We can make some guesses on Cecily’s education based on what we know of her more famous sister, Elizabeth, who could speak French, but not Latin. It’s also a safe bet that the younger girls – Anne, Katherine and Bridget – received a lighter, or at least more uneven, education thanks to the events of the 1480s and so Cecily likely benefited from her formative years occurring when they did. According to Alison Weir, Cecily’s letters from adulthood show “abominable” handwriting and spelling, either evidencing a lack of skill on her part or that more attention was paid to the education of her elder sister, Elizabeth of York.

Nevertheless, literacy was highly valued by both the King and Queen. Edward was a known collector of manuscripts and members of the Royal Family owned numerous books, which were both rare and expensive in the 15th century. Certain books are inscribed as being shared by Cecily and her siblings, indicating she had access to reading material and likely used them. Queen Elizabeth, meanwhile, was also the patron of Queen’s College, Cambridge, and Cecily would have grown up watching her mother’s work on behalf of scholars.

In October 1474, when Cecily was five, she was betrothed to James III of Scotland’s son, the Duke of Rothesay. The alliance formed as Edward planned an invasion of France and didn’t want Scotland to help France defend itself thanks to the auld alliance. Even so, the 1475 campaign was considered a military failure, though it ended in a sizable annuity paid to England by France and the betrothal of Princess Elizabeth to the dauphin (the future Charles VIII). As such, Cecily and Elizabeth grew up and came into awareness both as future queens and were styled “Princess of the Scots” and “the dauphine,” respectively.

In the meantime, all three were present when their younger brother, Richard, the Duke of York, was married to the Duke of Norfolk’s daughter and heiress, Anne Mowbray, in January 1478. Cecily sat with her parents, siblings and grandmother at the wedding in the Palace of Westminster’s chapel. Two years later, all three were made Ladies of the Garter and, by the early 1480s, marriage negotiations became more and more intense. Elizabeth was still promised to France and Cecily to Scotland, but Mary was briefly betrothed to the future King Frederick I of Denmark and Prince Edward to Anne of Brittany, heir to the duchy of Brittany, which would have dramatically changed the configuration of Western European power. Indeed, it’s interesting to imagine how this would have all panned out if Edward IV lived longer, for had he been successful then England might have entered the prosperity it did in the 16th century much faster.

For Cecily, she reached the milestone of 12 in March of 1481, the minimum age by which it was considered appropriate for young women to marry and James III began pressuring Edward to send his daughter across the border. Unfortunately, tension between England and Scotland was simmering and by 1482 the two countries were at war, with England supporting a rival claimant for the Scottish throne. Cecily’s betrothal was broken and she was instead briefly attached to the Duke of Albany, set on replacing James III on the throne with English backing. For better or worse, Cecily never made it to Scotland and she remained in England for the next phase of the civil war.

But before that happened, the family was struck by a personal tragedy when Mary died at the age of 14 in May 1482. While Edward and Elizabeth lost two children in infancy, they had been remarkably lucky in producing healthy children who survived the nursery. It’s unclear what she died of beyond a vague illness, but her tomb was discovered in the 18th century and opened. Her hair was described as pale blonde and her eyes, which were open, as light blue, though they turned to dust almost immediately after being exposed to the elements. Morbid, perhaps, but it gives a good indication of what Cecily and the rest of her siblings looked like.

The following April it was Edward himself who passed away, prematurely and tragically for his family. Without getting too much into the weeds of the events of 1483 (which you can read about here), what began with Prince Edward ascending the throne as Edward V ended in usurpation by Cecily’s uncle, the Duke of Gloucester, as Richard III. Edward V was conveyed to the Tower of London, while Queen Elizabeth and the rest of her children once again fled for sanctuary within Westminster, remaining there for over a year. The younger son, Richard, was removed from the Queen’s custody and sent to join his brother in the Tower.

This time, however, Cecily wasn’t an infant and at the age of 14-15 she had to have been affected by fear and anxiety over her family’s fate. While in sanctuary, Queen Elizabeth made an agreement with one of her former ladies-in-waiting, Margaret Beaufort, Countess of Richmond for the younger Elizabeth to marry her son, Henry Tudor, once he defeated Richard III. The plot was discovered, but even so, Henry Tudor pledged from abroad to marry Edward’s daughter and unite the two warring houses – specifically, he said that if he could not have Elizabeth, then he would marry Cecily.

That he would be able to was very much debatable by the dawn of 1484 and before the year was out Queen Elizabeth decided to try her luck at Richard’s court and left sanctuary, but not before he made a public promise not to harm his nieces. Cecily’s brothers, of course, had by now disappeared and their fate remains a mystery. Cecily moved with her mother and sisters to Heytesbury in Wiltshire, however that Christmas the family joined Richard at court. To say this would have been awkward is an understatement, for Richard’s claim to the throne was premised on Cecily and her siblings being bastards, the product of an illegal marriage between her parents. She was no longer a princess in the halls she walked, and what had once been considered home now belonged to the enemy, albeit one with whom they were currently making nice.

We have covered before the possibility of Richard III entertaining the idea of marriage to his niece, Elizabeth, before, but these months affected Cecily, too. Her betrothal to Scotland had long been broken and she was forced to stomach the insult of the Duke of Rothesay becoming engaged to her cousin, Lady Anne de la Pole, a daughter of her father’s sister, the Duchess of Suffolk, whose family had shown loyalty to Richard. As a Tudor chronicler later put it:

“Here may well be noted the disordered affection which this kind showed to his blood; for he, not remembering the tyranny that he had executed against his brother’s sons, the wrong and manifest injury he had done to his brother’s daughters, both in taking from them their dignity, possessions, and living, thought it would greatly redound to his honor and fame if he promoted his sister’s child to the dignity of a queen, rather than to prefer his brother’s daughter, whom he had disinherited.”

Nevertheless, Richard did orchestrate marriages for his nieces, perhaps knowing that they were less of a threat if he married them off to loyal men, making it harder for figures like Henry Tudor to use them as political pawns. Cecily’s younger sister, Anne, once been betrothed to Philip of Burgundy, was betrothed instead to Thomas Howard, heir to the dukedom of Norfolk. As for Cecily, she was married to Ralph Scrope of Upsall, second son of Thomas, the fifth Baron Scrope of Masham.

Tragedy of tragedies, we have no idea what Cecily thought of her husband, but it is mostly taken for granted that she felt it humiliating. She had once been preserved as a future queen of Scotland and instead found herself married to a relatively minor nobleman. At best, the match solidified her new station in life – that of a bastard daughter of a former king. Due to Cecily’s age and the marriage’s length, it’s a safe bet that the relationship was consummated, but unclear to what extent they lived together.

For Henry Tudor, biding his time abroad, it was nothing short of a disaster and, with Elizabeth still pointedly unmarried, it seemed to reinforce the rumors that Richard meant to marry her himself. While Elizabeth had four younger sisters, two of them were now off the market, and the youngest of the bunch, Katherine and Bridget, were mere children, while Henry would need to secure the succession as quickly as possible.

By the summer of 1485, Anne Neville was dead, the younger Elizabeth had been sent from court, and Cecily and her younger sisters were back in the countryside. That August, Henry defeated Richard at the Battle of Bosworth and he was declared King Henry VII and soon after the Titulus Regius, the legal instrument by which the York princesses were declared bastards, was overturned and destroyed. Still married to Ralph, Cecily joined her mother and sisters in London when Henry sent for his Elizabeth. Likely, given Ralph’s loyalties, he was either laying low or dealing with the physical and political repercussions of Bosworth.

Cecily lived at court with her family through the autumn and winter of 1485-1486. She served as her sister’s chief lady-in-waiting once Henry and Elizabeth married that January, and she attended upon her sister throughout the spring and summer while she was pregnant with her first child. When Prince Arthur was born in September 1486, Cecily carried the infant during his christening and handed him back to Elizabeth in her bedchamber after the ceremony.

By now, her marriage to Ralph had been annulled by Henry who was keen to do away with Richard’s supporters. After two years of marriage we have no idea what Cecily thought of the matter, but there is no record of her fighting it. The most interesting tidbit concerning Cecily from these years is that she formed a close attachment to Henry’s mother, Margaret Beaufort. She would have known Margaret well from her childhood when she served her mother as a lady-in-waiting, but of all the York girls, Cecily was one of the closest to her and it was she who likely facilitated Cecily’s next marriage.

At some point in December 1487, when Cecily was 18, she married John, Viscount Welles, Margaret’s younger half-brother. After the wedding, Cecily stepped down as her sister’s chief lady-in-waiting, a role that then passed to Anne, and lived quietly in the country. We have no idea whether she and John loved one another or even got along, but at the very least it was a slightly better match than her first marriage. John was somewhere between 15 and 20 years older than Cecily, but he was closely connected to the Tudor court by blood and she would have lived comfortably.

Unfortunately, Cecily was not blessed with the fertility of her mother or sister. She only produced two daughters that we know of, though there may have been stillbirths or infant deaths that went unrecorded. Her daughters, born around 1489 and 1491/2, were named Elizabeth and Anne and both died in the late 1490s. Indeed, the disease that killed them may well have been the same one which killed John, for Cecily’s husband passed away in February 1499. There was at least enough affection between them that he left the entirety of his estate to her, and the direction regarding his burial was that it be wherever she saw fit.

In the span of one year Cecily went from being a wife and mother, to once again being on her own. Her marriage had removed her from the major life changes underway at court, from the birth of several more Tudor princes and princesses, to the death of Elizabeth Woodville at Bermondsey Abbey in 1492. Cecily was notably not present at her mother’s funeral, perhaps because of pregnancy, however her husband attended on her behalf. In these new circumstances, Cecily returned to her sister’s household and resumed her duties as a lady-in-waiting.

She was present, then, in November 1501 when Katherine of Aragon arrived in England to marry the 15-year-old Prince Arthur. She was also on hand when envoys arrived in Scotland to negotiate the marriage between her niece, Margaret Tudor, and none other than her former betrothed, now King James IV. What she thought of her niece taking her place as queen of Scotland is anyone’s guess, but now in her 30s, she herself would have been deemed past her prime in terms of childbearing years.

Whatever the case, she was poised to make a major life decision of her own. At some point in the second half of 1502, Cecily chose to marry for love and wed Sir Thomas Kyme. Kyme was far beneath Cecily’s station and she apparently knew it wouldn’t be well-regarded by Henry, for she never sought his permission. When he found out, he banished his sister-in-law from court and took away her access to the Welles estate. Cecily was forced to turn to Margaret Beaufort, who swiftly offered the couple refuge at Colleyweston and began hammering out a financial agreement with the King. It’s unclear why Elizabeth herself didn’t intervene – and maybe she did privately – but it’s possible that she was more preoccupied with their sister, Katherine’s, situation.

By January 1504, Cecily’s interest in the Welles lands had been restored, but only for her lifetime. Under this arrangement she would have been unable to pass on the stake to any children she her marriag eproduced, though it’s unclear whether she ever did. Two children are mentioned in some records – Richard and Margaret – but since there weren’t titles or association with the Tudors, their lives (and existence, for that matter) are unclear.

Elizabeth died in February 1503 shortly after giving birth to her last child and while Cecily’s fate still remained unclear. Cecily herself passed away on the Isle of Wight on August 24, 1507 and is buried in Quarr Abbey there. Married to a man of no political importance and without great fortune, her last years were perhaps the quietest of all of her sister’s.

What Cecily made of her life is unknown. Did she wish she had made the glorious Scottish match? Did she resent having to attend on her sister or feel humiliated by her first marriage? We don’t know, of course, but I think there is something to be gleaned by her desire to throw caution to the wind by marrying for love near the end of her life after the loss of her first family. At the very least, her close relationship with Margaret Beaufort makes it difficult to believe so much of the hyperbole surrounding the Countess’s relationship with Elizabeth of York.