On May 3, 1446, Margaret of York was born into a family that guaranteed she would never know an ordinary life. Her father, Richard of York, was one of the leading claimants to the English throne, and her mother, Cecily Neville, known as the proud Cecily, was one of the most unyielding women of her era. Because of her father’s ambition, Margaret spent much of her childhood watching England tear itself apart in the Wars of the Roses. Victory shifted between the Houses of York and Lancaster like a tennis ball.
At one point, her father was forced to flee the country, and her mother had to beg the king for an allowance just to feed her children. Later, Richard came close to winning the crown, and the family paraded triumphantly through London. But in the end, he was killed by Lancastrian forces. Margaret’s childhood, shared with her brothers George and Richard, who were close to her in age, was turbulent, unstable, and dangerous, and the experience shaped her character for life.
When Margaret turned fifteen, her older brother Edward seized the throne and became King Edward IV. Her position changed overnight. She entered the circle surrounding the new queen, Elizabeth Woodville, and the Yorkist court taught her the subtleties of politics and intrigue. But as the king’s sister, she was also a piece on the diplomatic board.
A match of the highest rank was arranged for her: Charles the Bold, Duke of Burgundy. The journey to the altar took almost seven years because the king of France, who feared an English-Burgundian alliance, did everything he could to block the marriage. He tried to persuade the Pope to withhold permission and even spread a rumor that Margaret had an illegitimate child. Despite these efforts, the marriage contract was signed in 1468, and Margaret traveled to Burgundy to meet her husband.
Their first meeting produced an amusing moment. Margaret was exceptionally tall for a woman, standing at almost 183 centimeters, while Charles could not boast the same height. She had to lean down to receive her husband’s kiss. Contemporaries did not describe her as a breathtaking beauty, but she possessed something more valuable: intelligence and a gift for building relationships.
This set her apart from Elizabeth Woodville, who may have been beautiful but collected enemies faster than friends. Margaret immediately befriended her mother-in-law, Isabella, and developed a warm relationship with her stepdaughter, Mary. She also won over the people of her new duchy. When she was carried through the city in a litter before the wedding, she refused to hide from the wind and rain and instead waved to the crowd, showing her friendliness and goodwill.
The people of Bruges loved her wedding celebrations so much that they still recreate the ceremony in historical reenactments to this day. Margaret brought a magnificent crown with her from England for the wedding. It survives to this day and is one of only two medieval English crowns that have come down to us, since most royal jewelry was destroyed during the English Civil War. The crown is small, only about 12 centimeters in diameter, but Margaret likely wore it over a hennin, the fashionable pointed headdress of the time, which required women to shave back their hairlines and even remove their eyebrows.
The relationship between Margaret and Charles was apparently good, and there was no enormous age difference between them, but they never had children. Margaret hoped to become a mother since that was considered a woman’s duty, and her own mother had given birth to twelve children. Yet Charles spent so little time with his wife that historians can practically count their meetings on their fingers, and he did not even share her bed on their wedding night. Margaret directed her boundless energy toward her stepdaughter and toward helping her husband govern his enormous territories.
She traveled constantly, completing no fewer than twenty-eight ducal tours, an exhausting undertaking in an age without cars or airplanes. She raised money and gathered men for her husband’s endless wars while also supporting science and the arts. William Caxton, who introduced printing to England, counted Margaret among his patrons. On January 5, 1477, Charles was killed in battle against the Swiss.
Margaret was only thirty-four, a relatively young widow who could easily have remarried. Instead, she chose to devote herself entirely to her stepdaughter Mary. Without Margaret’s support, the young woman would have had almost no chance of saving Burgundy, her crown, or even her position as duchess from the French. Mary faced enormous pressure from the nobility and intense questions over whom she would marry.
Proposals poured in from every direction, hardly surprising given her dowry. Margaret recommended only one candidate: Maximilian, the eighteen-year-old son of Frederick III, the Holy Roman Emperor. Maximilian was as poor as a church mouse, but he could help Mary in her struggle against France. Mary followed her stepmother’s advice and married him, and the union turned out to be extremely happy.
The couple even shared a bedroom at a time when royal spouses normally slept separately. In gratitude, Mary rewarded Margaret with enormous wealth, making her the richest widow in Europe. Margaret repaid her with unwavering loyalty. Even when the French king tried to buy her support with a generous allowance, Margaret chose Mary.
She held Mary’s son, Philip the Handsome, in her arms during his christening, the same Philip who would later marry Joanna of Castile. Mary became not just a stepdaughter but a daughter, and through her Margaret gained a son-in-law and two grandchildren. She had a real family, even if not related by blood. But devastating blows were still waiting.
In 1482, Mary went hunting, fell from her horse, and injured her spine. She was pregnant with her third child and died several days later. On her deathbed, she begged Margaret to look after her children, and Margaret devoted the rest of her life to doing exactly that. News from her homeland was no better.
Her brother George, with whom she had shared a close bond, was executed on the orders of their own brother, Edward. Edward himself died soon after, and their younger brother Richard took the throne as Richard III. His reign was short, and he was killed in battle by Henry Tudor, who became Henry VII. The House of York had effectively fallen.
Margaret, a true white princess of York, was ready to support anyone who dared challenge Henry Tudor, the man she had come to hate. She first backed Lambert Simnel, a ten-year-old son of a baker or merchant. A priest named Richard Simon noticed that the boy resembled one of the princes in the Tower and decided to turn him into a prince. He later changed his mind and presented Lambert as the Earl of Warwick, the son of Margaret’s brother George.
The boy was taught courtly manners, rumors spread of a miraculously rescued heir, and Lambert was even crowned in Dublin. Margaret, hearing of her supposed nephew, sent two thousand Flemish mercenaries to Ireland to support him. The rebel army was defeated. The boy confessed everything, was pardoned by Henry, and given a job in the royal kitchens.
Margaret remained a thorn in Henry’s side and soon supported another claimant, Perkin Warbeck. This young man declared that he was Richard of Shrewsbury, Duke of York, the younger son of Edward IV. When he appeared at Margaret’s court in Burgundy, she immediately recognized him as her nephew, though it is unclear how she could have done so, having spent years away from England and having returned only once. Nevertheless, she began teaching him the details, secrets, and subtleties of life at the Yorkist court.
When Henry learned of this, he complained to Margaret’s grown ward, Philip the Handsome, but Philip would do nothing against his beloved grandmother. Maximilian, who maintained a warm and respectful relationship with Margaret years after Mary’s death, invited Perkin to the funeral of the Holy Roman Emperor, a gesture that amounted to open recognition of Perkin’s claims. Henry was furious and imposed a trade embargo on Burgundy, breaking off important commercial ties. In 1495, Perkin sailed toward the English coast to seize the throne.
Margaret hired mercenaries to accompany him. He also gained the support of the Scottish king, ever eager to trouble the English, who arranged for Perkin to marry one of his distant relatives. In the end, the young man proved far less skilled in warfare and intrigue than Henry. He surrendered, fell into the king’s hands, was imprisoned in the Tower, and executed several years later.
Realizing that Margaret might cause him trouble many more times, Henry VII agreed to restore trading relations with Burgundy only on the condition that the agreement explicitly prohibited her from helping any of the king’s enemies. This clause was included in the Treaty of 1496. Margaret publicly promised to respect the terms for the sake of her country’s interest, though what intrigues remained hidden behind the walls of her castles is unknown. Margaret devoted her final years to arranging the personal lives of her grandchildren.
Philip the Handsome married Joanna of Castile, whom he would later accuse of madness and who is known to history as Joanna the Mad. The younger Margaret married Joanna’s brother John, but he died within the first year of their marriage, and the child she carried was stillborn. Margaret helped raise the children of Joanna and Philip, including the future Emperor Charles V, who became one of the principal architects of the Habsburg empire. Margaret of York died on November 23, 1503, at the age of fifty-seven.
She was deeply mourned by the family not related to her by blood but whom she had chosen to make her own. Overshadowed by the famous figures of the Wars of the Roses, she was the one who kept Henry VII constantly on edge, held the French in check, and helped shape the future of the Habsburg dynasty. She may have been only one piece on the great chessboard of history, but she knew exactly how to move the others.
