On June 21st, 1529, Catherine of Aragon knelt before her husband of more than twenty years and pleaded for her marriage. Henry VIII had summoned her to a court that would decide whether their union had ever been lawful. He claimed the marriage was cursed because Catherine had first been married to his elder brother, and he believed God had punished them by denying a surviving male heir. Catherine, who had given him six children, answered with quiet dignity: by me you have had divers children.

Although it hath pleased God to call them from this world, which hath been no default in me. When Henry and Catherine married in June 1509, Catherine chose the pomegranate as one of the symbols on her coat of arms. It was an ancient emblem of fertility, closely tied to her native Spain, and she had every reason to believe she would bear many children. Her mother and sisters had all produced healthy offspring.

In November of that first year, Henry wrote joyfully to Catherine’s father that his daughter had conceived a living child. The kingdom waited eagerly for a Tudor heir, for the dynasty was still young and far from secure. Henry was only its second king. Around seven months into the pregnancy, Catherine went into premature labor and delivered a stillborn daughter.

Her abdomen did not appear to shrink, and her physician concluded she must be carrying twins, with a second child still alive inside her. Catherine withdrew to her chambers and waited for a birth that never came. There had never been a surviving twin; the swelling was likely a postpartum complication. Catherine called the loss a great calamity, and Henry supported her through her grief.

Before long she was pregnant again. Shortly after midnight on New Year’s Day 1511, she gave birth to a prince, named Henry and titled Duke of Cornwall. England rejoiced. Henry arranged magnificent celebrations and a great jousting tournament in honor of his son.

But while the festivities were still underway, the infant suddenly died. He had lived only fifty-two days. He was buried with full honors in Westminster Abbey, though his grave was left unmarked. His remains were discovered by chance during the Victorian era, making him the only one of Catherine’s lost children whose burial place is known today.

Catherine turned even more deeply to her faith. She spent hours praying on her knees upon cold stone floors and fasted to show her devotion. The physical deprivation and the rapid succession of pregnancies can hardly have helped her health. She is traditionally believed to have experienced six pregnancies, though some historians have suggested the true number may have been closer to ten, with several ending so early that they never became known beyond her household.

More than a year passed before Catherine announced another pregnancy. In the summer of 1513, Henry left England to campaign in France and appointed her regent. The Scots seized the opportunity and invaded, advancing toward Northumberland with an army said to number around eighty thousand men. Though heavily pregnant, Catherine traveled to within about two hundred miles of the front and helped rally the English forces with a passionate speech.

She did not ride into battle herself, but she proved a gifted leader. The Scottish army was defeated at the Battle of Flodden, and King James IV of Scotland was killed on the field. On September 17th, 1513, Catherine gave birth to another son. The child either died during the birth or survived only a very short time.

Henry never fully acknowledged either Catherine’s victory or her sacrifice. His political relationship with her father had become deeply strained, and that resentment began to affect the marriage. The baby Catherine expected in the summer of 1514 was awaited with particular impatience, in the hope that a child might heal the cracks appearing in the royal union. In November, she went into labor prematurely at around eight months and delivered a stillborn son.

The loss was doubly painful because a son might have restored her husband’s favor. Catherine remarked that God must love her greatly to have granted her the privilege of so much sorrow. Her prayers were finally answered on February 18th, 1516, when she gave birth to a healthy daughter, the future Mary I. It was not the long-awaited prince, but at last Catherine had a child who survived.

Both parents adored the little girl. Henry was a loving and attentive father to Mary during her childhood. When Venetian ambassadors congratulated him, he replied confidently: we are both young. If it was a daughter this time, by the grace of God, the sons will follow.

Two years later, Catherine became pregnant again. During the night of November 9th to 10th, 1518, she gave birth to another daughter. The baby was weak and died before she could be baptized or given a name. That pregnancy was the last of Catherine’s life, ending nearly a decade of almost continuous attempts to give Henry an heir.

While Catherine grieved what felt like her final hope of motherhood, Henry was already involved with one of her ladies-in-waiting, Bessie Blount. Their affair produced an illegitimate son in 1519, also named Henry, given the surname FitzRoy, meaning son of the king. Henry presented the boy at court as proof that he could father healthy sons. By 1524, he had stopped sharing Catherine’s bed.

She was thirty-nine, past the age at which Tudor women were generally expected to bear children. Soon afterward, Henry’s attention shifted to another lady-in-waiting, Anne Boleyn. Anne Boleyn also had every reason to expect many children. After her secret marriage to Henry, she became pregnant very quickly.

By the time of her coronation in the summer of 1533, her condition was obvious. Astrologers confidently predicted a prince. So much depended on the pregnancy that even the tapestries were removed from Anne’s chambers, for fear that the figures on the walls might influence the unborn child. On September 7th, 1533, Anne gave birth not to the expected prince but to a healthy daughter, the future Elizabeth I.

Henry’s disappointment was evident. Printed announcements celebrating a prince had already been prepared, and clerks were forced to add an S by hand, changing prince to princess. The grand celebrations planned for a male heir were quietly reduced. Only a few months later, Anne became pregnant again.

By January 1534, the Imperial Ambassador, Eustace Chapuys, was reporting the news. Henry commissioned a magnificent silver cradle decorated with precious stones. He even postponed a diplomatic meeting with Francis I of France. But the long-awaited prince never arrived.

The exact circumstances are uncertain; some writers have suggested a false pregnancy, but it is more likely the pregnancy ended in an early miscarriage leaving little evidence. By 1535, Henry’s passion for Anne had cooled. She had one more chance to give him a son. That autumn she became pregnant again.

On January 7th, 1536, Catherine of Aragon died, and it seemed Anne had finally triumphed. With Catherine gone, Anne was undisputedly Queen of England. Then disaster struck. On January 24th, Henry took part in a jousting tournament at Greenwich.

Something went terribly wrong, and the king was injured. The Duke of Norfolk broke the news carefully to Anne, who was pregnant and emotionally vulnerable. Henry was alive, and there was no reason to panic, but Anne was horrified. Had Henry died without a male heir, the Tudor dynasty could have been plunged into chaos.

Elizabeth was barely two years old, and it was uncertain whether the divided factions at court would have accepted her as queen. Henry regained consciousness after a few hours, but the shock left its mark. A few days later, on January 29th, 1536, the very day Catherine of Aragon was buried at Peterborough, Anne miscarried. She lost a male child believed to have been around fifteen weeks old.

Anne’s enemies later claimed the child had been malformed and would never have survived, but that story is not supported by reliable contemporary evidence. The main source behind the rumor was Nicholas Sander, a Catholic polemicist writing decades after Anne’s death, determined to portray her in the worst possible light. After losing the long-awaited son, Henry became convinced that God did not approve of his marriage to Anne. At the same time, Thomas Cromwell began setting in motion the plan that would destroy her, ultimately leading to her execution on May 19th.

On that January day, Anne did not lose only a child. She lost her final chance to secure her future. Had she given birth to a healthy son in the spring or summer of 1536, English history might have taken an entirely different course. The only woman who fully realized Henry’s dream was his third wife, Jane Seymour.

She gave him a legitimate son who survived infancy, the future Edward VI, but she died less than two weeks after giving birth. Henry’s subsequent marriages never produced another surviving heir. His marriage to Anne of Cleves was annulled, and both parties maintained it had never been consummated. Catherine Howard may have briefly carried a potential heir; several ambassadors reported rumors that the young queen might be pregnant, and Chapuys wrote that there was some presumption the queen was in the family way.

But nothing came of these reports, and the surviving evidence is too limited to know whether she truly became pregnant and lost the child early. Henry’s final wife, Catherine Parr, had no confirmed pregnancy during his lifetime. Her first and only confirmed pregnancy came after Henry’s death, during her marriage to Thomas Seymour. Why was a king so desperate for a son so unsuccessful in producing healthy heirs?

Over the centuries, many theories have emerged. Some researchers believe Henry may have been Kell positive, carrying a rare blood antigen that could have caused serious complications during his wives’ pregnancies. Others suggest Henry himself may have been a product of inbreeding, since his parents shared common ancestors, as did many royal families of the period. Generations of marriage within a limited group may have increased the likelihood of inherited health problems.

Another possibility is that Henry suffered from type 2 diabetes later in life, which can affect male fertility, though such a diagnosis remains extremely uncertain for a man who died almost five hundred years ago. The truth was likely a combination of genetics, illness, stress, repeated pregnancies, and the limits of sixteenth-century medicine. Henry left behind many graves, including those of his own children. The queens who married him were unlucky not only as wives but also as mothers, carrying fear with every pregnancy: the fear of losing another child, of disappointing a husband whose love was never unconditional, of losing their position, their security, and perhaps their lives.

In the end, these women and their children became casualties in Henry’s relentless race for an heir.