There was one thing that Henry VIII and his siblings had in common: marrying whoever they wanted. Certainly we know how Henry went about this, but less known is the extent to which his sisters did. After James IV of Scotland died in 1513, Margaret went on to marry twice by her own choice. Today, however, we’re going to take a look at their younger sister, Princess Mary, who did her duty by the king of France and then went the Tudor way.

Mary was born on March 18, 1496 at Sheen (later Richmond) Palace to Henry VII and Elizabeth of York. While not the youngest child to join the Tudor nursery, she was the last to survive and grew up the baby of the family. The carefree portion of her childhood, however, was brief. The year she turned seven she lost her mother when the Queen unexpectedly died after childbirth and her sister, Margaret, left England to marry the King of Scotland. Her brother, Henry, grew up with her in the same household and by all accounts they were the closest of any of their siblings.

For the next six years she played a typical ceremonial role at her father’s court, making a notable appearance in 1506 when King Philip and Queen Juana of Castile showed up for a visit in which her father pulled out all the stops. At At the time, Katherine of Aragon was living in England in a sort of limbo waiting for her fate to be decided – back to Spain as the Dowager Princess of Wales (Arthur’s widow) or on to Prince Henry as the future queen consort. She was treated shabbily by both her father and her father-in-law, but she was known to have a sisterly connection to young Mary, who may very well have seen Katherine as a sort of older replacement for the loss of Margaret.

After Elizabeth of York’s death, Henry’s court was a fairly masculine environment and Mary didn’t have a plethora of female guidance on which to rely. First and foremost she had her paternal grandmother, Margaret Beaufort, Countess of Richmond. To a lesser extent she had her maternal aunt and cousin, Katherine of York and Margaret of Clarence.

She was betrothed to Philip and Juana’s eldest son, Charles, in December 1507 after Philip’s death. As Charles was only seven, his rule was maintained by his paternal aunt, Margaret of Austria, Duchess of Savoy, but it was a good match for Mary. Not only did Charles stand to inherit Castile and Aragon through his mother, but the Holy Roman Empire through his father.

A year later, in December 1508, the couple went through the motions of a proxy wedding. Jousts, banquets and dancing were held in England and Mary was presented with letters from her new husband, as well as three jewels, including a ring that was inscribed in Latin with, “Mary has chosen the best part, which will not be taken away from her.”

Politically, the match was a good sign for Katherine of Aragon, who was still waiting to be married. It was around this time that rumors swirled of a possible double wedding between Mary and Charles and Henry VII with the widowed Juana, however the latter never came to fruition. Had it, it would have been yet another bond cementing England with Spain.

Instead, Henry VII died the following spring and Mary’s brother ascended the throne as Henry VIII. The new King quickly married Katherine and set his sights on war with France, falling for the idea of a Catholic alliance with backing from the Vatican checking French power. In theory, his marriage and the planned match of Mary to Charles should have all supported that. In reality, the military campaign on the continent was a disaster and it led to a war with Scotland that resulted in the death of their sister Margaret’s husband, James IV.

Even so, rumors swirled around Europe in the spring of 1514 that Henry was planning a triple alliance with the Habsburgs – Mary to Charles, his widowed sister, Margaret, with the Holy Roman Emperor and the Duchess of Savoy with his good friend, Charles Brandon. There were numerous problems with this idea, not least of which was that the Habsburgs were a snobby lot and the Emperor was horrified by the idea of his daughter marrying an Englishman of whom he’d never heard. The alliance, however preliminary the notion, was abandoned.

Within weeks news reached England that the Emperor and Katherine’s father, Ferdinand of Aragon, had made peace with the French, excluding Henry. Livid, the King quickly broke Mary’s looming marriage to Charles and on July 30, 1514 she was called upon to renounce the union in Essex. Reportedly, when Charles learned of the latest development he captured a hawk and plucked its feathers one-by-one, saying:

“Because he is young he is held in small account and because he is young he squeaked not when I plucked him. Thus you have done by me. I am young, you have plucked me at your pleasure and I know now how to complain. Bear in mind that for the future I shall pluck you.”

The political insult aside, given Mary’s reputation for being one of the most beautiful princesses in Europe, it’s very possible Charles was personally upset.

A week later England and France signed their own peace treaty, which was then followed up on August 13th by the proxy marriage of Mary and Louis XII. Before agreeing, Mary made her brother promise that if she married Louis she could choose a second husband of her own liking, and while this may be part-hyperbole, it has a grounding truth. For one, Margaret Tudor had first been put forth as a possibility for Louis, but she secretly married a Scottish man without Henry’s input, offering her sister an example for what form a second marriage could take. Secondly, Louis was hardly a catch, however much he was king of France.

Unlike the years-long betrothal of Charles and Mary, the French match moved quickly. Within six weeks, Mary was seen off at Dover by Henry and Katherine and then underwent a turbulent crossing of the Channel to reach France. She and Louis met by “surprise” in-transit in early October, jointly entering Abbeville where they planned to marry. It was here that Mary met her step-daughter, Claude, who was only three years younger than her and recently wed to Francis of Angouleme.

Louis and Mary were married on October 9, 1514, the bride dressed in gold brocade trimmed in ermine. After the ceremony Mary dined privately with her ladies-in-waiting before an evening of feasting and dancing where Louis is said to have danced like a man half his age, whatever that means. Of his wedding night, the King boasted to his attendants in the morning that he had “crossed the river three times that night and would have done more had he chosen.” Let that be a reminder that Henry VIII wasn’t the only wildly insecure Renaissance monarch.

Within days, Louis dismissed many of Mary’s ladies, including Lady Jane Guildford, who was a mother-figure to her. Lonely and genuinely afraid of what would happen when she was left at the mercy of the French, Mary pleaded with her brother and his adviser, Cardinal Wolsey, to help at least bring her back. Louis wouldn’t budge, but when his son-in-law, Francis, decided to issue a tourney challenge to the English in late October, she was saved by the arrival of Charles Brandon, Duke of Suffolk.

So, Brandon: Usually described as Henry VIII’s “best friend,” Brandon’s father died fighting for Henry’s father at the Battle of Bosworth when Charles was an infant. He was brought up at court and by the time he reached maturity, he was both handsome and well-positioned for a successful career alongside the Tudors. In 1506, he became involved with a well-connected young woman named Anne Browne. They were betrothed and Anne became pregnant, however Brandon didn’t go through with the wedding. Instead he jilted her for her much wealthier, older aunt, Margaret Neville, in February 1507 causing a full-blown scandal at court.

Anne’s family was livid and within months the marriage was declared null and void. Brandon went back to Anne, married her properly and their daughter, also named Anne, was born that year. A second daughter, Mary, came in 1510 and there may have been complications from childbirth, because Anne died soon after. Brandon was back on the marriage market.

In 1513 he be came contracted to Elizabeth Grey, Lady Lisle, his child ward, taking on the title “Lord Lisle,” though that was quickly trounced by Henry VIII naming him Duke of Suffolk in early 1514.

And thus, while we don’t know exactly when Mary and Brandon first came into contact with one another, it stands to reason it was years before Mary’s French marriage since they both essentially grew up at court. At the latest it was June 1507 when Brandon jousted during a tournament that Mary attended. That December, he jousted again in celebration of Mary’s betrothal to Charles of Castile. Once Henry VIII ascended the throne, Brandon’s high profile became even more pronounced, as did Mary’s freedom to partake more regularly in court life and cross his path.

Brandon acquitted himself well during the war in France in 1513 and he was with Henry when the latter went to Lille to visit the Duchess of Savoy. Since the Duchess was a widow twice-over (once to Katherine of Aragon’s brother, Juan of Aragon), it apparently entered into Henry’s mind that Charles should attempt to seduce her, or at least woo her. And while the Duchess may have enjoyed flirting, there was never a question she was going to marry him – when rumors began spreading that undermined her reputation, she was horrified. By the next spring when it sounded as though the English king was entertaining ideas of offering her up Brandon on a platter, she and her father quickly put a stop to it.

A few months later, Brandon was one of the witnesses who heard Mary renounce her Spanish marriage as she prepared to embark on her French. Thus, by the time Brandon showed up in France that autumn, he and Mary were already intimately friendly. And by all accounts, Mary had developed a bit of a crush on her brother’s dashing older friend – an attraction that may have been mutual, though we also can’t forget Mary was a princess and Brandon had a history of marrying ambitiously. Before Brandon departed, Henry made him swear not to seduce his sister.

Part of Brandon’s mission was to help coordinate a meeting between Henry and Louis the following year to plan a military campaign against Spain. He met up with the French court on October 26th, the King receiving him from bed where he was convalescing from a bad bout of gout (yet another comparison to an older Henry) with Mary by his side. Brandon traveled with the royal party as they continued to progress through the country, stopping on November 5th for Mary to be crowned queen at Saint Denis. From there, the party entered Paris so that Mary could be formally shown off and it was around then, on November 13th, that the tournament was held between the English and the French, Brandon performing particularly well.

On December 28, Louis wrote to Henry expounding on Mary’s virtues and showering Brandon with praise. By January 1, he was dead.

When the news reached Mary she formally proclaimed herself not pregnant, allowing the smooth succession of the crown from Louis to his son-in-law, Francis. She then barricaded herself in her darkened apartments for 40 days per French custom.

By the time news of Louis’s death reached England, Brandon had already returned home, but when Henry heard, he immediately ordered his friend back to help ensure the French let Mary come home. Both Henry and Francis had financial incentive for taking custody of Mary via her dowry and political incentive for arranging her next marriage. The choice of Brandon is a remarkable one given what it appears their relationship already was – with Mary now free and clear and Brandon not yet formally married to his ward, Henry would have been an idiot not to realize the two might seize the day and marry.

Reportedly, knowing that Mary wanted to take Brandon as her second husband, Henry made his friend swear that he wouldn’t take advantage of the opportunity until they both returned to England. Meanwhile, Mary learned that there was a good chance her brother would go back on his word and force her into yet another political alliance, this time back with Charles of Castile.

Brandon arrived in Paris on January 31 and met Francis at Senlis. In just a month on the throne, Francis had already managed to embroil himself in a scandal involving a woman by visiting her stepmother-in-law so frequently rumors circulated he meant to annul his marriage to Louis’s daughter, Claude, and marry Mary instead. Whether he ever had such an intention is unclear, but he does appear to have developed a good enough rapport that Mary confessed to him she wanted to marry Brandon.

To Francis, this was a relief. Letting Mary go back to England without any strings attached could very well have been disastrous for him, particularly if Henry did in fact marry her off in Spain. He went back to Brandon, letting him know that Mary had taken him into her confidence, displaying her trust in him by sharing a secret word that held some symbolism for Mary and Brandon. Stunned, Brandon immediately wrote to Cardinal Wolsey twice, both time swearing his allegiance to Henry and desire not to be deceitful.

Mary’s reunion with Brandon amounted to her clinging to him while hysterically crying. She spent the next days writing letters to her brother where she laid it on thick, reminding him of her loyalty and affection and, more importantly, his loyalty and affection for her. In the middle of February she confessed to Henry that she had told Francis she wanted to marry Brandon, asking him to write him on their behalf, which he did. However, she added the small detail that she had only done so to deny Francis’s own pursuit of her, which she said had become annoying.

By the end of the month Wolsey responded to Brandon that Henry intended to consider the proposed marriage, but only once Mary’s financial situation with the French crown had been sorted out. Apparently this wasn’t good enough for Mary and she convinced Brandon to break his promise and marry her immediately. They were wed in a secret ceremony at the Hotel de Cluny with Francis and a handful of other witnesses. The exact date of the wedding is unclear, but had to have happened in the very last days of February or early days of March. It was certainly done by March 5 when Brandon referenced the wedding as having already passed.

Brandon and Mary immediately wrote to Henry begging for his forgiveness, their marriage a calculated gamble. Mary’s letter is by far less conciliatory, however, as she takes the time to remind him that he promised her freedom in her second marriage. Henry, meanwhile, took his sweet time in responding, no doubt knowing that his silence was even more fearsome than his anger. Whatever his initial written response eventually was, it’s unfortunately now lost to us.

Mary and Brandon returned to England on May 2, Mary having been gone less than a year, all told. They were welcomed back by Henry, who made it clear he would forgive them, but at a steep financial price. Mary had to pay Henry back for the cost of her wedding to Louis, give up the jewelry she had taken to France, and Brandon had to give up his wardship of Elizabeth Grey.

Charles and Mary went through an English wedding ceremony on May 13, 1515 in the Church of the Observant Friars in Greenwich, marking Henry’s public acknowledgement that all was forgiven (so long as the money was paid). He even used it as an opportunity to hold a tournament.

In honor of the marriage Brandon wrote the following verse:

“Cloth of gold, do not despise,

Though thou be match with cloth of frieze.

Cloth of frieze, be not too bold,

Though thou be matched with cloth of gold.”

From then on, Mary devoted herself to finally being able to live a life of happy independence. The couple moved into Suffolk House in London and Westhorpe Hall in East Anglia and set about renovating them to their tastes. Brandon’s eldest daughter, Anne, had taken a position in the Duchess of Savoy’s household and Mary sent for her and his younger daughter to come live with them as a family.

In the autumn of 1515 Mary was back at court where she spent time with her sister-in-law, Katherine of Aragon. Both were in the last months of pregnancies, Katherine desperately needing a son – unhelpfully, the Queen gave birth to a daughter in February 1516, christened Mary, likely after Henry’s favorite sister. Mary, meanwhile, gave birth to a son that March and christened him Henry.

Before her son’s birth, Mary’s sister, Margaret, returned to England, having given birth to a daughter by her second husband. Her marriage in trouble, Scotland in turmoil and without custody of her son, James V, the visit may have brought some relief to the Tudor family, but the reunion was short-lived. When Margaret returned to Scotland in 1516, it was last time either sister ever saw the other.

In 1517, Mary and Katherine once more found themselves pregnant at the same time. For Katherine this resulted in a miscarriage and for Mary it led to the birth of her daughter, Frances, on July 16th.

Mary went on to have two more children, another daughter, Eleanor, in 1519, and another son, Henry, in 1523. The younger Henry replaced his elder brother who died in 1522, devastating his parents.

In 1520, then 24, Mary returned to her roots by swanning back to Henry’s court to play the ceremonial role of princess. That May England was honored by a formal visit by Charles of Castile, Mary’s one-time betrothed, only now he was Charles V, Holy Roman Emperor. Mary debuted an entirely new wardrobe for the occasion, delighting in the banquets and tourneys organized in his honor. For his part, he is said to have wept after seeing her, newly outraged that their marriage contract was broken.

When the Emperor left on May 31, so did everyone else. Mary accompanied Brandon, Henry and Katherine for the Field of the Cloth of Gold, an elaborately-planned meeting between Henry and Francis in Calais. What transpired was two weeks of merriment, jousting and literal feats of strength – archery, wrestling, fencing and, of course, diplomacy. Here, Mary was resplendent, honored as both an English princess and the Dowager Queen of France.

When it was all over, Mary – not Katherine – accompanied Henry and Brandon to visit Charles where she finally made the acquaintance of the Duchess of Savoy.

But if the first five years of her marriage were happy, the 1520s would make up a different sort of decade for Mary. The death of her eldest son and subsequent pregnancy took her from court and she appears to have spent considerable time in East Anglia with her children and stepchildren. Her marriage also seems to have become strained, in addition to money always being tight thanks to the debts they were paying to Henry, Charles took a mistress and fathered an illegitimate child around 1521.

In 1523, Brandon was sent by Henry to lead a military campaign in France, attacking Paris in the dead of winter. The assault was a disaster, but through no fault of Brandon’s, who did as well as could be expected. He disbanded the army, drawing the King’s ire and leading to a brief forced retirement for the Duke.

Certainly relations were back in place by June 1525 when Henry named Mary and Brandon’s son the Earl of Lincoln, the customary title for the heir of the Suffolk dukedom.

By the early 1520s, Henry took up with Mary Boleyn, sister to a young woman who had served his sister when she was queen of France. Indeed, one of the more interesting twists in the story of Anne Boleyn is that she first came into contact with the Tudors by serving Mary at French court, long before she met the King. By 1522, Anne was back in London, Mary Boleyn was sleeping with Henry and by the middle of the decade, her brother’s embarrassing and prolonged pursuit of her former damoiselle was on.

By 1527, Mary was horrified by her brother’s decision to not only aggressively pursue Anne, but a divorce from Katherine. After watching a court dance in which Henry had only eyes and hands for his would-be mistress, Mary expressed her displeasure and then abruptly withdrew from court. Their relationship never fully repaired and as the “great matter” waged on, Mary frequently retired from court, spending more time in the country.

Her animosity for Anne Boleyn was well-known, even by her brother. And while many others would lose their royal favor for saying and doing far less in the remaining years of Henry’s reign, Mary was always given a pass as his sister. Her behavior, including public statements denouncing Anne’s character and birth, did nothing to bring the siblings closer, but Henry pointedly never took action to punish her.

In 1528, Mary and Brandon took in another ward, Katherine Willoughby. Her mother, Maria de Salinas, was a Spanish lady-in-waiting of Katherine of Aragon’s who had married an Englishman. The couple planned to marry her to their son Henry when they were of age, her fortune and familial connections a good match.

By the early 1530s Mary’s health was on the decline. She passed away on June 25, 1533 in Suffolk at the age of 37, the same age that her mother, Elizabeth of York, died. And perhaps, on some level, the timing of her death was a blessing. When she passed away Henry had just managed to obtain his divorce and marry Anne, but she missed the true fallout of the Reformation, the destruction of the monasteries and the last decade of her brother’s reign which saw him go through four more wives.

Even closer to home, her son, Henry, died on March 1, 1534 at the age of 10 or 11.

Six months before – just three months after Mary’s death – Brandon chose to marry his son’s 14-year-old betrothed, Katherine Willoughby. The new adolescent Duchess of Suffolk went on to deliver him two more sons, however it would be his daughters by Mary who continued to be dynastically important.

Shortly before Mary’s death, her younger daughter, Eleanor, became contracted to Henry Clifford, heir to the earldom of Cumberland. The couple married in 1537 and produced three children, only one of which grew into adulthood – Lady Margaret Clifford who married into the Stanley family during Mary I’s reign. Eleanor died in September 1547, months after Henry VIII’s death.

Mary’s elder daughter, Frances, married Henry Grey, Marquess of Dorset the same year Mary died. Dorset was a great-grandson of Elizabeth Woodville via her first marriage, while Frances was her great-granddaughter via her second. Five pregnancies resulted in three living daughters, the eldest of whom was Lady Jane Grey. After Edward VI died in 1553, Frances and Dorset, in coordination with others, helped prop their daughter up as the Protestant heir to England’s throne in lieu of her cousin, Mary I. The rebellion failed, Jane and Dorset lost their lives, while Frances was brought back within the royal fold thanks to the family connection.

Frances made a second marriage later in life to the Queen’s Master of the Horse and had three more children who all died young. She passed away on November 20, 1559, a year after Elizabeth I ascended the throne.

Mary Tudor’s tomb can be found in Bury St. Edmund’s in Suffolk.