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Anne Boleyn in the tower

Who was Henry VIII's most unfortunate wife?

Anne Boleyn in the tower painted by Édouard Cibot

The story of Henry VIII’s wives is a well-trodden and universally known part of the Tudor king’s life and is possibly the most famous aspect of his reign other than his gargantuan style and reputation for dispatching people who displeased him. As some of his wives were luckier, or less unfortunate than others, it is interesting to see how the fates of six very different women played out during Henry’s most active years as a lover and monarch in pursuit of siring a male heir to preserve the Tudor dynasty. They are listed here in order of least fortunate.

Catherine (Katherine) Howard (1523 – 1542): Queen (July 1540 – Nov 1541)

Even though Catherine Howard, who married Henry as a teenager at just 17 years of age was only queen for less than a year and a half, her tragic end on the scaffold along with her illicit lovers makes her a contender for taking the shortest straw of all Henry’s wives. Raised in a household with other girls, where an atmosphere of sexual permissiveness saw the vivacious and naive Catherine experience underage sexual activity, the doomed first cousin of Anne Boleyn, was a victim of both her past and her lack of maturity to understand the consequences of her behaviour.

With a noble pedigree from the Howard family in Norfolk, Catherine’s early life was far from comfortable as her father was insolvent and after her mother died, 13-year-old Catherine was placed into the wardship of her father’s step-mother, the Dowager Duchess of Norfolk. It was while living at one of the houses run by the Duchess – but rarely attended by her – that Catherine, schooled for marriage, began having sexual relations with a young man, who would be the principal cause for her death as Queen of England.

Encouraged by more sexually aware girls in the mansion at Chesworth House, Horsham, Catherine was molested by her predatory music teacher, who may have pressurised her to lose her virginity to him. Later Catherine became the willing lover of one Francis Dereham, a young secretary of the Dowager, who arrogantly treated Catherine as his property and a ‘wife’ in waiting. The couple discussed a pre-contract intending to marry; an important factor relating to Catherine’s potential get-out clause to survive execution six years later.

When Catherine became a lady-in-waiting to Henry’s fourth wife Anne of Cleves - wife in name only - Catherine met Thomas Culpepper, a handsome courtier at the royal court and one of King Henry’s ‘favourites’. By the autumn of 1539, Catherine fell in love with him. Not long after Catherine’s infatuation with Culpepper began, Henry himself fell for Catherine and decided that she should be his wife.

The problem wasn’t that Catherine had been promiscuous before she married Henry, it was that she was pre-contracted to Dereham, a fact her family, the Norfolks, chose to conveniently ignore. On 28 July 1540, Henry married Catherine at Oatlands Palace. The young teenager, barely eighteen was now wed to an obese, irascible and ageing monarch, often in great pain due to his ulcerous and puss-seeping leg injury that was caused by a jousting accident. It could well have been this reality, compelled the young and often neglected Catherine to reignite an affair with Culpepper, possibly as a means to become pregnant by him when the king was physically unable.

By spring 1541 Catherine and Culpepper’s assignations were secretly facilitated by the scheming Lady Jane Rochford, (sister-in-law of tragic Anne Boleyn), often at night and while the royal couple were on a tour of the country. Catherine’s infatuation with Culpepper’s - who would later deny having sexual relations with her - was soon to be discovered when her past relationship with Francis Dereham came to light when servants back at Chesworth House began to spread gossip. After blackmailers from Chesworth failed to attain positions at the royal court through Catherine’s patronage, her past indiscretions reached the ears of the Archbishop of Canterbury. Through painful torture, Dereham revealed that Catherine was having relations with Culpepper and that they had planned to marry during her time as maid-of-honour to Queen Anne of Cleves.

What has now become a legendary story detailing Catherine’s tragic end, Henry refused to see his wife as she desperately pleaded for his forgiveness. She was dragged by guards screaming down a corridor at Hampton Court. Henry, having been given proof of her affairs with both men, refused to see her again. Incarcerated at Syon House in Middlesex by the river throughout the bitterly cold winter of 1541, it was here that the hysterical and incoherent Catherine was interviewed. Had she admitted her pre-contract to Dereham, the disclosure may have saved her from death, as it would have annulled the royal union and seen Catherine banished. Instead, a Bill of Attainder found her guilty of treason for failing to disclose her sexual history to the king, a crime punishable by death.

On 10 February 1542, Catherine was taken by barge downriver to the Tower of London. During her last solitary days, it was here that the pitiable and doomed teenager found the strength to face her execution and requested the ‘block’ be brought to her cell so she could practice her death by axe. Henry was more unfavourable to Francis Dereham accusing him of ‘spoiling’ Catherine and sentencing him to the gruesome and inhuman execution of being ‘hung, drawn and quartered’. Thomas Culpepper was spared a similar fate and beheaded swiftly on the same scaffold. Lady Rochford, for her part in abetting the young queen’s amorous meetings with Culpepper, faced the same end as her cousin Anne Boleyn six years earlier, but on Tower Green watched by commoners. At 7am, on 13 February 1542, Catherine Howard, despite being terrified climbed the scaffold in the Tower and with admirable fortitude and dignity gave a short traditional speech before she was blindfolded and beheaded. The still teenage girl, who was referred to as the ‘old man’s jewel’ as Henry’s young nubile wife, was a tragic character who didn’t deserve the cruel punishment that ended her short life.

Anne Boleyn (1501 – 1536): Queen (May 1533 – May 1536)

Possibly the best known and famous of all Henry’s wives, since Anne Boleyn and King Henry’s passionate relationship ended so violently, both emotionally and physically, with Henry ordering Anne to be beheaded on the grounds of treason. Anne who was educated at the French court was not known to be a great beauty but possessed charm, wit and sexual magnetism that caught the eye of Henry when she was about 25 years-of-age; she famously kept the philandering monarch on a leash until he promised to marry her. The result was the greatest political and religious schism in Europe; marrying Anne forced Henry to break from the Pope and church of Rome and set himself up as the Head of England’s church, defying Catholic Europe.

For a woman who had been pre-contracted to marry another man, before the King decided to woo her as his mistress, Anne Boleyn’s story is particularly unlucky and tinged with irony. Indeed, Anne may have led an uneventful but happy life with her first love Henry Percy, before the most powerful man in England cast his eye over her.

Boleyn was doubly unlucky that her presence, not only at the royal court, made a public loyal to Henry’s first wife Catherine of Aragon, view her as the king’s ‘whore’, making her enemies from the start. Her foes multiplied as her reformist views about religion became known. By the time she was into her second year of marriage to Henry, vociferous factions dedicated to destroying her and the Boleyn family were in full throttle.

Anne Boleyn’s punishment for not producing a male air was far harsher than Catherine of Aragon’s, her previous rival who was divorced and dismissed out of sight. Anne found herself victimised by a court led by Henry’s right-hand man Thomas Cromwell, a power-obsessed schemer, determined to see her executed. At just 36 years of age and having only been married to the king for three tumultuous years and bearing one child, a daughter Elizabeth, Anne Boleyn’s world crumbled. Her last days in the Tower before approaching the scaffold, where she was famously beheaded by a French swordsman, saw her deliver one of the most famous and generous speeches to the very man, King Henry, who had moved the earth to marry her.

Jane Seymour (1508 – 1537): Queen (May 1536 – Oct 1537)

Henry’s third wife Jane Seymour might not have been the most scintillating of his wives – unlike the feisty and challenging Anne Boleyn – but she did provide King Henry with the much longed-for living male heir, he had so desperately sought to continue the Tudor line. Henry’s secret betrothal to Jane Seymour took place at Hampton Courts twenty-four hours after his previous wife’s execution. Ironically, despite Henry’s concerns about offending ‘God’ – as he believed he had done by marrying Catherine of Aragon, his brother’s widow – he and the then 27-year-old Seymour who were fifth cousins required a dispensation for the marriage. Anne Boleyn’s heraldic leopard was transformed into Jane Seymour’s heraldic panther after the royal union. But this pasty-faced third wife was nothing like a cunning feline. She was servile – at least on the surface – and appeared willingly compliant to a man who had tired of challenging wives.

The new bride soon learned to conduct an elaborate game of Grandmother’s Footsteps with the volatile king.

What the egotistical, didactic and increasingly weighty monarch craved was stability in a wife who would adore him, not question him, cause agitation, and most importantly provide him with a son. In Jane Seymour, he found the perfect candidate. When Henry’s new bride looked out on a procession of 2,000 men and hundreds of constables in scarlet to celebrate the royal marriage, Seymour had already won the hearts of the English people through her support and compassion for the divorced Catherine of Aragon and her step-daughter Mary, the estranged princess who she helped reconcile with Henry. It is doubly ironic therefore that such grandeur and expense at the beginning of her marriage to Henry turned out to be a short-lived union, one that was ended because of her precious gift to Henry, a healthy boy, was to be her greatest sacrifice.

The Wiltshire born daughter of Sir John Seymour and Margery Wentworth was not well educated and her skills restricted to elaborate needlework and household management. Like Anne Boleyn before her, she was also a maid-of-honour to King Henry’s first wife, Catherine of Aragon. Jane was said to be gentle and meek but no great beauty. Despite her motto ‘Bound to obey and serve’ she was no complete cypher and had to be rebuked by Henry against ‘meddling’ in political matters. The new bride soon learned to conduct an elaborate game of Grandmother’s Footsteps with the volatile king. In February 1537, Jane discovered she was pregnant and took to her chamber in late September. After a difficult labour, she gave birth to a boy, Edward, on 12 October. At the age of forty-six, King Henry finally had a son and his love for Jane was forged for eternity.

The following celebrations that involved hogsheads flowing with wine, church bells ringing every night and the noise of 2,000-gunshots from the Tower were to be replaced within days with national mourning when Jane fell ill with a puerperal fever which turned into septicaemia due to lack of hygiene. At midnight on 24 October, Queen Jane Seymour at just 29 died. She has been queen for less than eighteen months. An emotional King Henry dressed in mourning apparel until February 1538.

Catherine of Aragon (1485 – 1536): Queen (June 1509 – May 1533)

Queen Catherine of Aragon, was Henry VIII’s first wife by default, having been originally betrothed to his elder brother Arthur. The young teenage girl, at just 15 had recognised the duty of a princess and taken the daunting step of arriving in a cold alien country for her wedding. That short-lived betrothal and the issue of whether or not it was consummated was to become the focus of Henry’s attempts to divorce her over two and a half decades later.

What was designed as a marriage to consolidate relations between England and the most powerful country in the Western World, Spain, ended in trauma for Catherine and a schism between England the rest of Catholic Europe. Catherine’s downfall began in December 1525, when after years of devotion to her husband, Henry fell in love with another woman, Anne Boleyn. It was the beginning of the end of a union that had won the love and loyalty of England’s citizens. The desperation of the king for a male heir saw Catherine treated cruelly. She was not just pushed aside for a younger woman of child-bearing age, she lost her status, her courtly comforts and was prevented from seeing her much loved daughter Mary, as she was shuttled between series of backwater houses and castles. Henry saw Catherine for the last time in July 1531 without bidding her farewell. After twenty-two years of marriage, he simply took to riding out with his lover Boleyn, leaving the unhappy Queen to find that he had gone...forever, out of her life. ‘Tell the Queen that I do not want any of her goodbyes’ retorted Henry to a messenger, believing that Queen Catherine, who stood resolutely against him divorcing her had caused him no end of trouble.

Despite Catherine’s protests to the King that she was his legitimate wife and engaging the support of both the Pope and the Emperor, Catherine’s nephew Charles V, the increasingly ill queen, who, 28 years earlier had been a radiant and adored new bride of Henry, was unceremoniously dismissed as an inconvenience and treated with contempt. She died broken-hearted but still, not just in her mind but the majority of England’s populace remained Henry’s true queen.

Catherine Parr (1512 – 1548): Queen (1543 – 1547)

The sixth and last of Henry’s wives may have survived the royal union from divorce, banishment or the axe but she wasn’t immune to having her life threatened by a pathologically paranoid and immobile monarch, beset by crippling pain and a waistline of 54 inches. Henry’s gargantuan size brought about through ill health, injury, overeating and lack of exercise meant he had to be moved with the help of mechanical inventions. By the time his advisors were looking for a new wife after the ill-fated teenager Catherine Howard, a new clause had been set, which made it explicit that any woman put forward to be Henry’s wife and was found not to be chaste when pretending to be so, would see her and any members of her family concealing such knowledge punished for treason. The consequences were at best imprisonment and at worst the axe. The days of inserting a young nubile woman in front of Henry’s eyes for marriage was over and his advisors understood that.

Finding a suitable match for a volatile royal invalid in decrepit health and famously known for having beheaded two of his wives and divorcing two, did not endear the English monarch to European princesses. Neither did Henry want to remarry Anne of Cleves who he had dismissed as unsuitable years before. In 1543 courtiers noted new life in the king and a re-energised bonhomie. It was an apt moment for Henry to cast his approval of his next wife, known as Lady Latimer, also known as Catherine Parr, a tall, plain but lively widow at 31-years-of-age who far from being dull was intelligent, an exquisite dresser and loved dancing and music. Her patronage of musicians (from Venice and Milan) and artists, revealed a creative spirit. What made Parr satisfactory as a sixth consort was primarily because she was a widow twice over, which removed any pretence at being a virgin. Like three others of Henry’s queens, Catherine had been a lady-in-waiting to Catherine of Aragon.

Parr had a lot of experience in running a large house which was left by her deceased husband John Neville, 3rd Baron Latimer to whose daughter, Catherine was a kindly step-mother. As Latimer’s health declined she fell in love with Sir Thomas Seymour, brother of Henry’s third wife Jane Seymour. But the shadow of the galleon sized King Henry loomed large over Catherine, who first received his attention while Baron Latimer was dying in February 1543. Torn between love for Thomas Seymour and duty, she chose duty, a move which later enriched and ennobled many members of her family.

King Henry married Catherine Parr on 12 July 1543 at Hampton Court. The wedding was unlike Henry’s previous marital celebrations. This time there was a sense of union and peace as Henry’s daughters Mary and Elizabeth, newly restored to the succession line along with their young brother Edward, all attended. Possibly realising that Catherine was to be his last wife and having little urgency to sire a male heir may have allowed Henry to be happy, as his contented bloated face showed during the ceremony.

Proving to be a dependable nurse-maid for King Henry and an agreeable companion, who could deal with his tantrums, Queen Catherine Parr also showed commendable skill at acting as regent while Henry was occupied with a French campaign abroad. She also won over Henry’s children as a much-loved step-mother to the very different siblings, elder Mary, her step-sister Elizabeth and their young step-brother Edward. However, Catherine did suffer a brief and frightening moment when her fate could have led her to the scaffold. It was her subversive views on Evangelical matters, despite her outward appearance of conformity that was to ignite fury in Henry.

Catherine’s interest in religious reform with a radical Evangelical slant and her belief the bible should be read by ordinary people put her on the road to heresy. Her actions involved exercising her influence to protect reformers and even inviting them into her household. By doing so she created tension between herself and the Catholic factions at court.

In 1546 the pace of persecution towards heretics gathered speed and particularly against those with connections to the court. Worse for Catherine, she lectured Henry, who in a state of physical agony and irritability was vulnerable to being persuaded by Catherine’s enemies that she should be charged with heresy. The panic-stricken queen, fearing the same fate as Anne Boleyn and Catherine Howard had to resort to a performance of self-abasement and grovelling supplication to appease the enraged Henry. She didn’t flunk it and saved her neck, but only just.

Henry died on 28 January 1547. Six months later Catherine married her fourth husband, the man she loved before Henry, Sir Thomas Seymour. Sadly, their union was short-lived when she died a year later due to complications during childbirth.

Anne of Cleves (1515 – 1557): Queen (Jan 1540 – July 1540)

Despite being the most maligned Queen due to legendary tales of her looks which King Henry took exception to, Anne of Cleves (Anna von Kleve in her native German) came out triumphant from her brief marriage to Henry, making her one of the richest women in England and living a relatively trauma-free and relatively long life for the time. But her journey to riches and fame involved the most humiliating of starts.

The conventional method for selecting an eligible princess was either through a personal inspection by an entrusted envoy or through commissioning a portrait. It was Hans Holbein’s famous portrait of Dusseldorf-born Anne that became the source of controversy and which led to the most famous of romantic u-turns in royal history. After several attempts to impress Henry with paintings of willing princesses, Holbein was sent to paint Lady Anne of Cleves, who was way down the list of top contenders. The young German-speaking lady, one of four children, had the political advantage of representing the territory of Lower Rhineland that proved strategic in a climate where Henry’s England was often at loggerheads with either France or Spain.

Henry requested Holbein to be as accurate as possible when painting Anne at around age 23 and her younger sister Amalia, who was also being considered as a wife for Henry. In what felt like a rushed arrangement to get Henry and Anne betrothed, the king’s right-hand man Thomas Cromwell appeared to have overlooked the fact that his master admired cultural sophistication in women and the poorly educated Anne had no such attributes. She was unable to play an instrument, dance or show any artistic talents expected of Renaissance nobility. Neither could she speak English. Her accent known as ‘deutsch’ was also oddly grating to English ears. Despite being pleased by Holbein’s portrait, Henry’s first glance of the German princess in the flesh has gone down in history with varying degrees of interpretation.

One popular story is that Henry disguised himself before entering the room where Anne was waiting for her introduction at Rochester Abbey on New Year’s Day 1540, shortly after she had arrived from Dover. The prank backfired spectacularly with Anne displaying a mix of bewilderment and repulsion at the appearance of an overweight man, bursting like a bull into her room. Henry, taken aback by this lack of reverence by his kingly presence took to disliking the nervous maid who failed to enchant a corpulent, testy husband, uncertain of his virility and who was twenty-five years her senior. Possibly as a defensive reaction Henry is alleged to have complained that she was ugly and nothing like the painting he had admired. In reality, even though she was not conventionally beautiful, Anne had been painted by Holbein ‘full-face’, which although the fashion, may have been intended to conceal fewer appealing features such as her high forehead, pointed chin and heavy-lid eyes.

The King’s disappointment in his new German bride reached its peak on the wedding night of 6 January 1540 when it is alleged that the marital bed was left cold and without sexual union taking place. It is this claim by Henry that he was unable to consummate the marriage due to lacking desire for Anne that was to set in motion a speedy chain of events that resulted in an annulment being granted within six months. One humorous story which has entered folklore and could be apocryphal was that instead of consummating the marriage, King Henry and Queen Anne played cards all night. It was one recreational skill she was good at. The divorce was granted for two reasons, non-consummation of the marriage and the question of a pre-contract between the Lady Anne and Francis of Lorraine. To counter any rumours of impotency, Henry’s physician stated that the king experienced ‘nocturnal pollutions’ during sleep.

Lady Anne survived all of Henry’s wives and even the King himself.

Although Lady Anne's moment as Queen of England was brief, lasting less than six months she saw her life enhanced by the fact that she received a generous settlement which included magnificent palaces including Richmond Palace and Hever Castle, the family home of the doomed Anne Boleyn. As Anne evolved with confidence and the ability to speak English she became a trusted figure in the royal household, particularly with Henry’s children and cultivated a friendship with Henry devoid of the tensions associated with his previous wives. She was even referred to as ‘the King’s Beloved Sister’, endearing her as a companion to Henry’s fifth wife, the ill-fated Catherine Howard. In fact, so jolly were King Henry and Lady Anne together by the August of 1541, that rumours began to spread that he was about to restore her to her previous position. But Anne was no fool and understood that her good fortune as one of the wealthiest women in England and a respected ex-wife of Henry was due to bowing to his will and massaging his ego.

Lady Anne survived all of Henry’s wives and even the King himself. As a much-admired member of the royal court, she also took part in the coronation procession of Henry’s eldest daughter Mary on 28 Sept 1553. The new Catholic reformist Tudor Queen remained on good terms with Anne and allowed her to live at Chelsea Old Manor when the then 40-year-old unmarried maid suffered ill-health. Lady Anne's one regret was that was unable to return to her family home in the Rhineland having signed a binding contract that prevented her from going overseas. But compared to five of King Henry’s wives, two of whom suffered humiliating divorces, two who were executed and one who died in childbirth, Lady Anne can be seen as the most fortunate of his queens. Anne of Cleves died, most probably of cancer, on 16 July 1557, eight weeks before her 42nd birthday.