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Introduction

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The life of Henry VIII (see plate 1) is probably the best defined of any king of England. Plays, films and television series have focused on Henry’s life, particularly in relation to his six wives. Put simply, he loved his first wife, Catherine of Aragon (see plate 4), but divorced her because she failed to give him a son and grew old and unattractive. He married Anne Boleyn (see plate 6) for love and beheaded her when she, too, failed to give him an heir. Jane Seymour (see plate 7) was the quiet wife who died giving him that longed-for son. Anne of Cleves was the undesired one; Catherine Howard (see plate 8) the promiscuous one; and Catherine Parr the wife who survived Henry. However, this view portrays Henry as a two-dimensional, almost cartoon character, as epitomised by the Holbein painting (completed 1537) where he is dressed in red and gold, a massive figure standing, legs akimbo, seemingly the Lord of the World. In line with this image, he selects women to share his bed with a snap of his fingers and discards them just as easily when they cease to please him. All that matters to Henry is a male heir and nothing is allowed to stand in the way of his getting what he wants.

Of course, the real Henry Tudor is far more complicated. This book looks beyond Henry VIII’s six wives, examining the women with whom the King had, or is believed to have had, affairs and the illegitimate children he is believed to have fathered. Beyond the limits of policy and diplomacy, it presents the King as a serial monogamist, a man who spent his life searching for the one, perfect woman he was destined never to find.


Henry was born a second son: he spent his childhood in the shadow of an elder brother who would one day be his king and master. In the space of less than a year, however, he had lost both his brother and his mother. He became the adored and vital eldest son, the Prince of Wales, the future king – and everyone around him suddenly treated him as such. He was expected to be stronger, wiser and more talented than anyone else. That Nature endowed Henry with a beautiful face, an admirable body and a quick and receptive mind led him eventually to believe all those who told him he was the best and worthy of the best.

While he did not lack male role models in his childhood and youth (his father; brother Arthur; great-uncle Jasper Tudor, who died when he was four; his mentor William Blount, Lord Mountjoy; companions such as Charles Brandon, John St John and Edward Neville), Henry lacked close female company. He had two sisters, but Margaret, two years older, was never a friend and Mary, five years younger, was too much the baby to be of interest. The most formidable lady in Henry’s world was his grandmother, Margaret Beaufort, a woman devoted to the point of obsession to her only son, Henry VII (see plate 3). A woman of strong character, Margaret was already well past middle age, religious, a widow, obsessed with family, monarchy and wealth – Margaret, in fact, was the real power behind the throne. Elizabeth of York (see plate 2), Henry’s mother, was not allowed to play a significant part in his life as his father and grandmother ruled his household. Mother and son only met on the occasions when Henry VII and Elizabeth visited the young Henry or he was brought to Court (in 1494, aged three, Henry came to London to be made a Knight of the Bath and Duke of York, for example). He also knew of Elizabeth from ballads sung about her:

In a glorius garden grene

Sawe I syttyng a comly queen

Among the flouris that fressh byn.

She gaderd a floure and set betweene;

The lyly-whighte rose methought I sawe … 1

Elizabeth of York embodied perfection to Henry, a view endorsed by everyone at Court. She was beautiful, elegant, serene, gentle, loyal, loving – everything that a wife and queen should be. Thus, Elizabeth became the ideal against which all the ladies in Henry’s life were to be measured, and those that pleased him most invariably resembled her. Catherine of Aragon, his first wife and arguably Henry’s true love, probably came closest. She was every inch a queen, Henry’s intellectual equal, lover, friend, companion and counsellor. Catherine became to Henry what he perceived his mother had been to Henry VII.

There was a strong element of subservience in Elizabeth’s relationship with Henry VII. Her motto was ‘Humble and Reverence’ and when Henry VII set Margaret Beaufort up as Elizabeth’s superior in matters of state or, indeed, their personal life, Elizabeth appears to have said nothing. She bowed to her husband in every way, striving to serve him as the perfect wife and mother to his children. There is no record that she ever spoke out against him or contradicted him. Henry VIII similarly expected his ladies to treat him with humility and reverence. His favourites were those who followed his lead, made his opinion their own and sought to please him. Jane Seymour, first mistress and then queen, was a case in point; a large part of her charm was her total acquiescence to Henry’s personality (this is discussed further in Chapter 10). Anne of Cleves, his wife, earned his friendship by giving in to him; on the other hand, Catherine of Aragon earned his enmity when she stood up against him. Anne Boleyn was beloved until she started arguing; and his last queen, Catherine Parr, almost lost everything when Henry believed that she was trying to influence him – to be the teacher in the relationship rather than the pupil (this is discussed further in Chapter 12). But where did this pattern begin?

The centre of attention from an early age, Henry became Prince of Wales at 11. By the time he was 14, he had started to take an interest in girls – to put it in context, the minimum age for marriage was 12 for a girl and 14 for a boy at the time. Life expectancy in the 16th century was about 35 and infant mortality was high and so it was not uncommon for a young couple to start their family in their mid to late teens. Henry was 19 when he came to the throne and he quickly married Catherine of Aragon, but it is highly unlikely that he was a virgin. Elizabeth Denton, a lovely lady and a servant of his family, was probably the first in what was a romantic, but stage-managed love affair organised by Henry VII and Margaret Beaufort (this is discussed in Chapter 2). However, when Henry became king, his only thought was to marry Catherine, his brother Arthur’s widow, and set her on the throne at his side.

Perhaps one obstacle to Henry and Catherine enjoying a fairytale union was that they belonged to an age and to a social class that considered extramarital affairs for men as perfectly normal. The king was practically expected to take a mistress. Henry’s grandfather, Edward IV, had been incredibly promiscuous; his great-grandfather, Owen Tudor, had a bastard son through a sexual liaison, as had his great-uncle Jasper Tudor. Henry VII, despite a reputation for fidelity, also had an illegitimate son, Sir Roland de Velville. It was, therefore, almost inevitable that Henry VIII would follow suit. He was, after all, extremely handsome and sexually desirable. The wealthiest and most powerful man in England, Henry was a leader of fashion and the focus of a Court that lived for pleasure. Women, often with the support of their families, quite simply threw themselves at him. Lord Herbert of Cherbury summed this up when he wrote, ‘One of the liberties which our King took in his spare time was to love … so it must seem less strange if amid many fair Ladies, which lived in his Court, He both gave and received temptation.’2


One of Henry’s earliest mistresses, Anne Hastings, became the object of his attention while Catherine of Aragon was pregnant for the first time, and Henry was excluded from her bed. The affair was light-hearted, and would most probably have passed without incident but for the Duke of Buckingham, Anne’s brother, who made the matter public and caused a scene. For a while after that, Henry returned to connubial bliss, although Catherine lost her baby, but when he took his armies to France in 1513, on his quest to conquer French territory, he fell in love with Etionette de la Baume, a lady of the Court of Margaret of Austria. Their affair was passionate, but brief – an amusing interlude on his part and a political manoeuvre on hers (this is discussed in Chapter 3). On Henry’s return to England, with his wife pregnant again, Henry enjoyed another brief fling, this time with Jane Popincourt. These relationships were primarily harmless and fun.

If one looks at Henry’s affairs of the heart, they can be divided quite neatly into those ladies who were important to him – and those who were not. His first wife, Catherine of Aragon, obviously was, but Anne Hastings, Etionette de la Baume and Jane Popincourt were not.

Henry’s first big extramarital romance came in 1514 when he fell in love with Elizabeth (Bessie) Blount. She was his ideal woman: young, beautiful, intelligent, acquiescent, well raised, musical, an enthusiastic rider and a graceful dancer. While Catherine remained his wife and the future mother of his heir, Henry was no longer deeply in love with her. In a very short time, Bessie Blount came to mean everything to him and for five years they enjoyed each other, a physical relationship that only ended when Bessie informed the King that she was pregnant. A husband was quickly found for Bessie – a little late admittedly – but Henry publicly acknowledged their son, Henry Fitzroy (see plate 10), the future Duke of Richmond and Somerset – the only one of his illegitimate children that he did so with. The affair had been public, added to which the boy looked just like Henry and, perhaps more importantly, Bessie did not initially have a husband who could usefully take responsibility for the child. This affair and its outcome taught Henry a valuable lesson. From then on those ‘light-hearted’ mistresses had husbands that could ‘hide’ any child born to such a relationship.

Mary Boleyn (see plate 5), the first of the Boleyn women with whom Henry had sexual liaisons, was another such light-hearted lover. As soon as Henry declared his interest in her she was found a husband. Although some historians believe that Mary was a woman of loose morals – one who had been the mistress of Francis I of France – I do not believe that this is the case. Mary had sexual relations with only three men: Henry and her husbands, William Carey and William Stafford (discussed further in Chapter 5).

Henry’s affair with Mary lasted until she had her first child, who arguably may have been Henry’s. However, thanks to a compliant mistress and her even more compliant husband, no one needed to know. As the husbands of the King’s ex-mistresses, Gilbert Tailboys (Bessie Blount’s husband) and William Carey (Mary Boleyn’s husband) never had reason to complain. They acquired charming, agreeable wives with equally acceptable dowries and also the sincere gratitude of their monarch.

Perhaps it seems strange that Henry’s affairs with Bessie Blount and Mary Boleyn lasted for years and only ended when the ladies became pregnant. Was it that Henry could not accept a mistress who was also a mother? Did he feel that these children were, in some way, a kind of betrayal or danger? From personal experience Henry knew that bastards could potentially threaten a weak king or one without legitimate heirs. His own claim to the throne came from two bastard lines that had resulted in his father Henry VII, a man capable of toppling a dynasty.

Another way in which Henry could have felt betrayed is if he thought the pregnancies were deliberate. Both Bessie Blount and Mary Boleyn enjoyed five years of sexual intimacy with the King before they fell pregnant with their first children, suggesting that they were using some method of contraception. The experienced Catherine Howard is supposed to have commented, ‘a woman might meddle with a man and yet conceive no child unless she would herself.’3 Contraceptive methods existed, such as condoms, made of fine lambskin, known as ‘Venus gloves’4 but they were cumbersome to use and not always successful. The use of pepper as a spermicide was also unreliable. Anal sex was also recognised as an effective method of birth control. These methods, however, were considered immoral, if not illegal, between a man and woman as God had ordained sex as a means of procreation and to prevent it was contrary to the laws of God.

Although the pregnancies of Bessie Blount and Mary Boleyn may both have been accidents, the pregnancies of Henry’s later liaisons with Jane Stukeley, Mary Perrot and Joanna Dingley may have been more the result of his carelessness. Perhaps he practised unprotected sex with them, not caring if he impregnated them or not? After all, Henry did not have to acknowledge any children or worry about them making any later claims to be his offspring. In an age without blood tests or DNA testing, claims concerning paternity were extremely difficult to prove or disprove. They relied on the characters of the parents, the physical appearance of the child and reports on the relationships of the wife. The wife of William Knollys, the grandson of Mary Boleyn and William Carey, finally had children after 20 years of childless marriage, when he was in his 80s. Suspiciously, his widow, Elizabeth, married Lord Vaux immediately after his death, but Knollys was no fool: his will did not acknowledge any children and he was officially recorded as having died without heirs. His ‘son’ was subsequently refused a place in the House of Lords on the grounds of ‘adulterous bastardy’.5

By the time the King met Anne Boleyn, Henry had fallen out of love with Catherine of Aragon. They barely spent any time together and even the pregnancies that failed to go to term or ended in stillbirths had stopped. Henry was ripe for a real love – a deep, honest, true love that would replace what he had once had with Catherine. Anne Boleyn was the woman he chose, but it didn’t stop Henry from continuing to enjoy other brief, light-hearted affairs. Jane Stukeley, Mary Perrot and Joanna Dingley, all of whom are discussed later in this book, belong to this group and it may be that there were others too. Each of these aforementioned ladies had a child whom contemporary records claim was fathered by the King. The boys, Thomas Stukeley (see plate 11) and John Perrot (see plate 12), were said to resemble Henry VIII rather than the husbands of their mothers. All three ladies were considered to be ‘safe’ by Henry: Jane and Mary were married, while Joanna was a recent widow and would soon marry again. At a time (1526–33) when Henry VIII was being put through emotional turmoil by Anne Boleyn’s refusal to become his lover and then by her increasing desire to become his wife, he must have found occasional passionate but meaningless episodes with beautiful, adoring, willing partners absolutely irresistible. None of these ladies would further complicate an already complicated situation by suggesting marriage.

Henry’s wives, on the other hand, were part of an elaborate political network. When Henry married Anne Boleyn and their relationship became increasingly strained, Margaret Shelton, Anne’s cousin, became his mistress for a short time. It may even be that Anne herself supported this move; if the King were to stray, much better that he do so with a member of the Boleyn–Howard faction (see page 102 – the Boleyn–Howard family tree) rather than with a lady belonging to some other great family reaching for power who would try and replace the Queen. When Anne finally fell from favour, it was Jane Seymour who used Anne’s own strategy to get her way; she refused to surrender her virtue and held out for marriage. She was supported by a rival Seymour-based faction trying to oust the Howards from power.

When Jane Seymour died, after having given birth to Henry’s son, the pattern changed. Having three illegitimate sons must have helped convince Henry to keep trying for a legitimate male heir with his wife, whoever she might be, and Edward’s birth lifted the major pressure of securing the succession from Henry’s life. Now his aims became different, as he looked beyond his own borders to select a queen for political gain. It was one of history’s great ironies that, when faced with Spanish, French and Italian beauties, he ended up with Anne of Cleves, the plain daughter of a German duke. History usually has Henry turning straight from Anne to Catherine Howard, but, in fact, once Henry had decided that the Cleves marriage must be ended, he took a little time to find her successor. He had access to the Queen’s ladies-in-waiting, the usual hunting ground for a king in search of female interest. He had met Bessie Blount when she was lady-in-waiting to Catherine of Aragon; Mary and Anne Boleyn both came to his attention through the same route, and Jane Seymour had been Anne Boleyn’s lady. Now from amongst Jane Seymour’s ladies, Henry showed interest in Anne Bassett, Elizabeth Brooke and Elizabeth Cobham, before finally settling on Catherine Howard, the most unsuitable lady of all. Catherine Howard had a loving nature and absolutely no self-control when it came to personable young gentlemen. She was devoid of any sense of self-preservation, actually bringing two ex-lovers into her household while she was Queen, one of whom she had previously acknowledged as her husband.

After Catherine Howard followed Anne Boleyn to the scaffold, Henry settled down to a quiet and contented old age with Catherine Parr, but old habits were hard to break. Whether he loved Catherine or not, it didn’t take long for Henry to become irritated with her extreme Protestantism, and in the last months before his death, he was considering yet another change of wife. Katherine d’Eresby (see plate 9), widow of his best friend, Charles Brandon, was a good-looking lady and a renowned wit. She expressed her opinion freely without fear and was said to be deliciously malicious in her humour. Katherine’s spice was attractive to the ageing Henry, but he never came to enjoy her charms and wit for himself. He died on the night spanning 27 and 28 January 1547.

Henry VIII enjoyed the reputation of a womaniser, but he was never in the league of other kings such as Charles II (1630–85; king of Great Britain and Ireland, 1660-85). He did not have a harem, although some historians suggest otherwise. He was a serial monogamist and was essentially a man who loved being in love. He was the king and a handsome, intelligent and charming man into the bargain. He could have ordered any woman to his side, yet he set out to charm and to win; writing letters and poems, composing songs, sending gifts, arranging meetings, and behaving, in fact, like any lovelorn teenager. For Catherine of Aragon he arranged jousts and masques in the disguised character of Sir Loyal Heart. Mary Boleyn had a ship named after her. Anne Boleyn received love letters and jewels for years while she admitted her love for him, yet refused Henry a physical relationship. Jane Seymour was lodged in a house Henry could visit by secretly slipping away from Court. Anne Bassett was given a riding horse and saddle, and moved into the healing atmosphere of the country when she fell ill, and Catherine Howard was showered with clothes and jewels. Henry gave generously and expected complete adulation in return. He wanted to be forever that young man who had taken possession of a throne, the Great Lover, whom no woman could resist.

Other Tudors: Henry VIII's Mistresses & Bastards

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