Born right in the middle of the Wars of the Roses, Princess Cecily of York’s life was like a bloody episode of Game of Thrones made all too real. Except that was just the beginning: After surviving countless attempts on her life and honor, Cecily grew into a hardened and clever woman unwilling to back down from a fight…and her defiance came with a brutal price tag.
There’s a reason no one knows about Cecily of York—but it’s your turn to find out.
When Cecily was born in 1469, she came into the world as a Princess of England. After all, her father was King Edward IV and her mother was the renowned beauty Queen Elizabeth Woodville. But from the beginning, something was seriously wrong. In truth, Cecily didn’t inherit a shining realm, oh no. Instead, she was princess to a crumbling kingdom.
The infamous Wars of the Roses were already ramping up, and they were about to baptize Cecily into a brutal game of thrones.
Back before Cecily was born, her father Edward had deposed the old King Henry VI—and when Cecily was just a year old, it came back to bite the royal family in the butt. In 1470, the disgraced Henry played tit for tat, gathering supporters and completely ousting Edward, who had to flee to the continent for safety. In an instant, little Cecily’s life went from charmed to traumatic.
With her father gone and her royal titles in serious jeopardy, Cecily spent her toddler years in “sanctuary” in Westminster with her mother, hoping that the storm would blow over. It was a nightmarish existence in more ways than one. At the time, Cecily had two older sisters and her mother was heavily pregnant with another child, but the vulnerable brood had to share just a few small cramped rooms while praying for their lives.
Yet just when all hope seemed lost, fate dealt Cecily and her family another curveball.
After six excruciating months, Cecily’s father finally pushed himself back onto the English throne, reinstating the family and turning the tables once again. On top of that, Cecily’s mother gave birth to a baby boy, also named Edward, and then later to a son named Richard. With these surprising turns of events, the happy fate of the Yorks seemed sealed. Key word: seemed.
If anyone thought Cecily could escape from these early horrors scot-free, they were very wrong. They shaped her forever after—and as we’ll see, there was much more tragedy on the way.
No sooner was Cecily back as a Princess of England than her father started making big plans for her. In yet another bid to solidify the family’s power, he betrothed her to James, the Duke of Rothesay, the son of the current King James III of Scotland. This was utterly scandalous. Yes, both Cecily and James were only a handful of years old at the time, but the biggest problem came from an entirely different quarter…
Although Cecily’s betrothal to the Scottish noble earned her the rather fetching title of “Princess of Scots” for much of her young life, Scotland itself was none too pleased with England’s grand plans for their royal daughter. They didn’t like London encroaching on their freedoms at the best of times, and this seemed a bridge too far. Maybe that’s why the engagement unraveled so spectacularly.
In 1481, Cecily turned 12…and nearly kick-started another war. See, 12 was considered prime marrying age for girls at the time, because everybody knows a 12-year-old can carry a child to term. Accordingly, Scotland’s King James thought it was high time for King Edward to cart his daughter over the border to get hitched, and he started sending some serious nudges. It couldn’t have gone worse.
In 1482, the one constant in Cecily’s life shattered. Although she had spent most of her life as the “Princess of Scots,” that year England and Scotland got into an enormous political spat, and Cecily’s father retaliated by breaking off her engagement. Yeah, you read that right: Cecily’s own father used her as a pawn in a disastrous 15th-century game of The Bachelor.
The girl hadn’t even hit puberty yet, and she’d been through the wringer—but that was nothing compared to what was just around the corner.
In 1483, when Cecily was just coming to her teenage years, the worst disaster the girl had ever seen hit her family. Her father Edward passed on, throwing the Yorks into a state of utter turmoil for the second time in Cecily’s short life. Sure, Cecily’s younger brother Edward became Edward V, ascending to the throne after his father. But oh boy, things didn’t stay rosy for long.
Both little Edward V and Cecily’s even younger brother Richard were painfully inexperienced and green. As a result, no one could save them from the wolves at the door—or rather, wolf. With Cecily and her family still mourning their father, her uncle Richard, the then-Duke of Gloucester, swept in and tried to finagle the throne for himself. The results have lived on in infamy, and they must have shaken Cecily to her core.
With the English throne in a tenuous position, Cecily experienced a horrific betrayal. First, Uncle Richard insisted on locking both of her brothers in the Tower of London for “their own safety”…and then immediately began claiming that all the York children were illegitimate swine and that he was the true heir. His smear campaign worked, and in January 1584, he officially took the throne as King Richard III.
By this time, the women had fled to sanctuary again, and Cecily had to watch, terrified for her life, as it all went down. When the dust settled, her blood must have run cold.
Throughout the new King Richard III’s usurpation of the throne, people would see Cecily’s little brothers playing in the courtyard of the Tower of London, and the women of the royal family could breathe a sigh of relief that they were still alive. This didn’t last long. At the end of the summer of 1483, those sightings abruptly stopped. There was only one conclusion Cecily could have drawn—and it was utterly grisly.
At this point, the royal family must have suspected (rightly) that King Richard III had executed both young boys, making sure that Cecily had no brothers left and the Yorks had no more true heirs. But this isn’t close to the end of the story. The York women, Cecily included, were fighters until the end. While holed up in sanctuary, they came up with a plot to exact revenge.
The Wars of the Roses weren’t short of blood feuds and rivals, and Cecily and her mother got to work finding the most formidable enemy to take down her Uncle Richard. They landed on Henry Tudor, a distant relative and the son of one of the most cunning women in court, Margaret Beaufort. Spoiler: The York women do not miss—it was a very good choice.
As it happened, scores of people were currently backing Henry to take over the throne. But Cecily’s role in this came with a twist. Making friends with Margaret Beaufort, they offered both Cecily and/or her older sister Elizabeth up as potential brides for her son Henry, as their lineage would strengthen his claim to the throne. Yeah, that’s a little icky…but it gets grosser.
See, since Elizabeth was the older sister, she got first dibs on Henry if he became King. Cecily, meanwhile, was officially sloppy seconds. And I do mean officially: Henry made a proclamation stating that Elizabeth was number one, but if she passed on from illness or some other twist of fate before Henry could topple Richard, he’d take Cecily, I guess. Aw, that’s one way to make a girl feel wanted. But as it happened, Cecily had bigger problems.
Some months into King Richard III’s dubious reign, Cecily’s mother Elizabeth Woodville decided it was high time to break out of sanctuary and start making some political moves. This had a terrifyingly high cost. Cecily and her sisters’ lives were still very much in danger, and the matriarch had to make Richard swear he wouldn’t harm his nieces before they stepped out.
If you have to extract that kind of promise from someone…maybe heading out of sanctuary isn’t the best thing. And you can bet this led to one awkward encounter.
In Christmas of 1484, a teenaged Cecily accompanied her mother for a stay over at King Richard’s. It must have been a true nightmare: After all, her uncle had not only killed her brothers, but had also thrown her legitimacy into question when he took the throne. Now here she was in the royal palace that used to be hers, stripped of her titles and prestige. Only, Richard had one more knife to twist into her ribs.
Around this time, Cecily’s uncle put her in her place in a brutal way. Remembering Cecily’s broken engagement to the Scottish prince James, he actually engaged his other niece, Cecily’s cousin Lady Anne de La Pole, to the Scot. Though the marriage never went through, it still rubbed it right in Cecily’s face that her family was no longer in power, and she was no longer a princess deserving of a prince. Um, but Richard didn’t stop there.
Unwilling to just leave poor Cecily alone, Richard came up with yet another way to torment her. In the early 1480s, the King actually did marry her off…and it was about as far from a prestigious union or a love match as you could get. The lucky bridegroom was the humbly named Ralph Scrope, a second son of an eminently unimportant baron.
In fact, up until his wedding day to a former princess, Ralph’s biggest achievement in life was being a loyal King Richard III supporter—which is what got him the gig in the first place. Need I say the marriage was horrific?
It’s hard to imagine sharp, battle-worn Cecily looking at her new husband Ralph with anything but disdain, but that’s not why her marriage was awful. It was awful because it barely lasted—and it went down in a blaze of glory. In 1485, just as Cecily’s wedding bells stopped pealing, Henry Tudor finally came through for the Yorks, slaying Richard III in the Battle of Bosworth Field and becoming King Henry VII of England.
One of Henry’s first acts was to annul Cecily’s sham marriage since he had no use for an old supporter of Richard in the family. This, however, got a lot more scandalous than you’d think.
While her lowborn marriage likely humiliated Cecily, she was with Ralph long enough that they had almost certainly consummated their union. Technically, this should have made getting an annulment much trickier...but not for Henry VII. Whatever a King of England wants, a King of England gets, and by 1486, Cecily was a free woman. And believe me, she was in her glory.
For the first time in her life, Cecily was securely on top of the world. After taking power, Henry made good on his promise and married Cecily’s sister Elizabeth, making our girl the sister-in-law to the Queen of England, not to mention an aunt to the heirs the royal couple were already popping out. When Crown Prince Arthur was born in 1486, Cecily even carried the baby to the christening ceremony.
If Cecily had her way, it probably would have stayed like this forever. But: Nope, absolutely not.
Being a woman in the 15th century was one raw deal, and Cecily learned that lesson the very hard way. Just a year after she finally became single again, Henry VII married Cecily off to one of his supporters, Viscount John Welles. To be fair, John Welles seemed like a semi-decent man, and he was the half-uncle of the king, so it was a step up from poor old Ralph. But that doesn’t mean it was easy.
At this point, the 18-year-old Cecily was in the bloom of her youth….while John was at least 15 years old than her, maybe 20. So, old enough to be her father, at least by Medieval standards. Even so, with her sister as queen and her family finally safe from the horrors they had trudged through, Cecily wasn’t about to mess this up. She set about doing her duty and making babies—but like everything else, this didn’t go to plan at all.
Although many of the women in Cecily’s family, including her mother and sister, were extremely fertile and had scads of children, Cecily didn’t have it so easy. She may have suffered from multiple miscarriages or stillbirths, and in the end, she only had two daughters with John, Elizabeth, and Anne, who were born in the late 1480s and early 1490s.
Now, don’t get me wrong, that’s accomplishment enough, especially given the maternal medical care of the day—but it still took a massive toll on her.
While married to John Welles and trying to grow her family, Cecily was very far removed from life at the Tudor court. For example, she was barely present at court when her infamous nephew, the future King Henry VIII, was born, and likewise with his sisters Margaret and Mary. In some ways, it was a peaceful existence for Cecily at long last—but it also led to great tragedy.
In the summer of 1492, more horrible news hit Cecily: Her mother, the dowager Queen Elizabeth Woodville, had perished at the age of 55, far away from where Cecily was living. To make matters worse, new evidence also hints that Elizabeth may have perished from the plague. Now, I wish I could say that Cecily rushed out to bury her mother, but that’s not what happened at all.
Sadly, Cecily failed her mother at the last moment. She didn’t attend the funeral, although she did send her husband John in her stead. To this day, no one is sure why she didn’t come, although some believe Cecily could have been pregnant at the time and unable to travel the distance to say one final goodbye. Either way, it wasn’t long before disaster decided to strike again, and this time it took everything she loved.
In the late 1490s, Cecily experienced her worst heartbreak yet. Her two daughters, still young and vulnerable, fell ill and died one after the other, likely from another illness that was sweeping through England. Cecily herself—survivor that she always was—seemed unscathed, but before she could get back on her feet, another strike came and knocked her right back to the ground.
While Cecily was still reeling from the loss of her two girls, her husband John Welles also passed on in 1499. In a cruel twist, some historians suggest that given the closeness of their deaths, John may have succumbed to the very same illness that ended his daughters and annihilated Cecily’s nuclear family. It was all way more than Cecily could take—and she broke.
We don’t know much about the intimacies of John and Cecily’s relationship while he was alive, but we do know Cecily must have come to love the older man eventually. According to historical records, Cecily deeply grieved his passing, and John, in turn, left much of his property to her, saying it was she “whome I trust above all oder.”
Given the heart-wrenching loss of her beloved husband and children, maybe it’s no surprise Cecily did a complete about-face.
Almost immediately after this series of horrific tragedies, Cecily jumped right back into life at the center of the Tudor court. She was even present at the wedding of her now-teenage nephew Prince Arthur as he married Catherine of Aragon; in fact, it was Cecily who held Catherine’s train as she walked down the aisle on the big day. But that wasn’t the only way Cecily made her mark.
After a decade of living as the distant aunt, Cecily became the woman about the palace. She deepened her friendship to King Henry VII’s mother Margaret Beaufort—after all, they were both high-performing women—and showed an excellent mind for finances, even lending her sister the Queen money in 1502 from her own coffers. But as always, Cecily’s life took another strange detour.
By 1503, Cecily’s old fiancé James, the Duke of Rothesay, had actually become King James IV of Scotland—and he waltzed back into her life in the strangest way possible. And no, he didn’t come as Cecily’s suitor. Instead, the grown man married her barely teenaged niece, Margaret Tudor, making her the Queen of the Scots instead of Cecily. Um, and it got more cringey than that.
Because Cecily had made herself so indispensable to the Tudors at this time, she, unfortunately, got a front-row seat as she watched The Scot Who Got Away marry her relative. She was even present when Scottish envoys arrived to negotiate the marriage treaty. Not where I’d want to be. And, well, that might be why Cecily went and messed it all up for herself.
Just a few short years into her widowhood, Cecily met Sir Thomas Kyme, an unknown and entirely unremarkable Lincolnshire squire. Then the strangest thing happened. Despite her first unequal marriage to the forgettable Ralph Scrope, Cecily found she quite liked the modest Thomas—in fact, she loved him. And you know what they say, love makes you do some crazy things.
After meeting Thomas, Cecily made a jaw-dropping announcement to the royal court. She hadn’t just gone and fallen in love, she’d gone and married Sir Kyme without anybody’s permission—in particular, without the permission of her brother-in-law, King Henry VII. That was one huge faux pas for the time…but Cecily may have had ulterior motives for her nuptials.
Even people during Cecily’s day knew her third wedding was, as one source put it, "rather for comfort than credit,” since Thomas was dirt poor. Yet some historians believe that besides her real affection for Thomas, Cecily was also being as cunning as ever, trying to choose a husband who King Henry VII wouldn’t be jealous of, nor see as a court enemy.
So when she presented herself as a married woman that day, she probably thought it would all go smoothly. She was so, so wrong.
Instead of viewing her love match with happiness, King Henry VII viewed it with fury. Henry despised that she had gone behind his back to find a husband, rather than letting him make another advantageous match for her. And, despite the fact that Cecily was his wife’s sister, Henry wasn’t willing to show her any mercy nor give her any quarter for her error. Instead, he gave her a bitter punishment.
Before Cecily could counteract the King’s fury, Henry had banished her and her new husband entirely from his court. And he just kept going. He also confiscated every last estate Cecily had in her name, essentially driving her into poverty. After a lifetime of surviving for herself, Cecily’s hard-won independence was under threat—but she knew just what to do.
Before King Henry VII decided to exile Cecily, he should have taken a better measure of the kind of woman he was dealing with. Using the cunning she had developed throughout the Wars of the Roses, Cecily called in one of her allies to help—none other than Henry’s domineering mother, Margaret Beaufort. And as always, she was the right person to call.
Margaret Beaufort had always liked and supported Cecily, and she wasn’t about to let one of the few powerful women in England lose out on all of her influence, especially not because of her hare-brained son. This led to Cecily’s first coup. With Cecily ousted from the central court, Margaret offered up her own Collyweston Palace for the couple to stay at. And then she gave her son a royal talking to for the ages.
Margaret gave King Henry VII a motherly tongue-lashing that was so definitive, Henry had no choice but to put his tail between his legs and partially recant his punishments. He eventually gave some of Cecily’s lands back to her, a reversal few absolute monarchs would ever want to make. Still, even with this victory, Cecily’s future was far from comfortable…or content.
Cecily may have gotten her lands back, but she had to give up one crucial right. Although she had those lands for her own lifetime, Henry absolutely denied her the ability to pass them on to Thomas Kyme or any of the children she might have with him. Likewise, none of her children could have any royal titles. There’s no doubt that this led to Cecily’s utterly tragic end.
For all that she fought tooth and nail to keep what she had earned throughout her life, Cecily all but fades away during these final years. Moreover, thanks to King Henry’s ban on passing down any of her titles or her lands, Cecily’s ancestors also disappear. She may have had two children with Thomas named Richard and Margery, but they are so obscure they may not even exist at all.
Although the York women were survivors, weathering the Wars of the Roses even as the bloody conflict felled many men, they were not very long-lived in the end. In 1503, Cecily’s older sister Queen Elizabeth of York died after a post-partum infection on her 37th birthday. King Henry VII and the nation mourned her…but sadly, Cecily’s fate was somehow worse.
Cecily didn’t survive her sister Elizabeth long—and, like Elizabeth, she never got to see her fourth decade. In 1507, when the princess was just 38, Cecily succumbed to illness. She got only a few precious years with Thomas Kyme, the man she had given up everything for. And after her passing, the crown dealt her one final betrayal.
King Henry VII always made good on his oaths, and he made sure that no one would remember the defiant Princess Cecily in the years to come. To this day, no one is even sure where she was buried. Besides that, most mentions of her in the history books call her the wife of John Welles, completely erasing her rebellious third marriage. There is, however, one trace of Cecily left.
Thanks to King Henry’s brutal agenda, we have very little material evidence about Princess Cecily of York’s life—save for one spectacular example. A stained glass portrait of her father Edward IV’s family is still in existence, and one panel depicts all his daughters lined up together, including Cecily herself. A modern restoration now sits in Canterbury Cathedral. Take that, Henry VII.
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