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Portrait of a Young Woman c. 1540–1545 from the Workshop of Hans Holbein the Younger

Did Catherine Howard cheat on Henry VIII?

Catherine Howard married the 49-year-old King Henry, aged just 17, a first cousin of the doomed Anne Boleyn she was Queen for only eighteen months

Portrait of a Young Woman c. 1540–1545 from the Workshop of Hans Holbein the Younger, thought to be of Catherine Howard

Two wives of Henry VIII were led to a scaffold on Tower Green at the Tower of London and executed. Both were cousins and accused of adultery and treason and both women had aristocracy in their blood and were once loved by a King once obsessed by them. But where one was a victim of trumped-up charges to get rid of her by the state, the other is believed to have been guilty, if not of a plot to replace the King or bring harm to him, then certainly to betray him sexually and possibly emotionally, for the love of a younger man.

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

Catherine Howard married the 49-year-old King Henry, aged just 17 A first cousin of the doomed Anne Boleyn she was Queen for only eighteen months. Her tragic story involves abuse, manipulation and unfortunate circumstances that took her promising life as one of the youngest Queens in English history to the executioner’s block with the hectic pace of an unstoppable juggernaut. Whereas there is doubt about King Henry’s second controversial wife Anne Boleyn’s alleged trysts with male admirers, there is little conjecture about Catherine Howard’s extramarital affair with a respected courtier, while she was married to the infamously obese and mobility restricted Henry Tudor.

Orphaned nobility

The turbulent and short journey of Catherine Howard from a vivacious, giggly and somewhat unsophisticated young girl, to adored teenage wife and Queen of Henry VIII, begins when she was 13 and placed into the wardship of her father’s stepmother, Agnes Howard, Dowager Duchess of Norfolk. Chesworth House, situated in West Sussex’s idyllic countryside was run by the Duchess as a Tudor finishing school for young women, mainly to instruct them in conventional skills of the time in preparation for marriage to men of nobility. Despite its serene and convent-like appearance, close to the River Arun, it was far from respectable behind its brick-clad timber walls.

Seduction and grooming

Finding herself in a heady atmosphere of adolescent sexual adventures at Chesworth, where some of the more advanced girls enjoyed liaisons with male visitors, Catherine was most likely seduced and forced upon by her predatory unmarried music teacher Henry Mannox. It is unlikely that the Duchess was aware of the secret and more salacious activities taking place at the 14th-century mansion but the staff, notably some of the housemaids, were very much privy to the amorous assignations taking place in dormitory bedrooms and the grounds with local males. Mannox, who was possibly only a few years older than Catherine, may have pressurised the still underage girl to lose her virginity to him, despite Catherine’s claims during later interrogation that she was repulsed by him and did not indulge in full coitus apart from exchanging light sexual favours.

Secret pre-contract

By 1538 Catherine was free of the manipulative Mannox and his insistent pestering due to him being relocated to the Duchess’s mansion in Lambeth. Soon afterwards another young man, Francis Dereham, Secretary of the Duchess at Chesworth House, set his sights on the possibly still virginal and by now 15-year-old Catherine. With an arrogant streak, the equally predatory Dereham treated Catherine as his property and a ‘wife in waiting’ as both lovers were known to address each other as ‘husband’ and ‘wife’. The relationship soon became common knowledge to Catherine’s roommates and also the Dowager Duchess’s attendants, as the young couple even discussed a ‘precontract’ intending to marry; an important factor relating to Catherine’s arrest for treason four years later.

Betrayal by letter

Catherine and Francis Dereham’s relationship, which is believed to have been emotionally sincere, came to end when a spiteful Mannox, consumed with jealousy, sent a letter to the Duchess suggesting she visit the teenage girl’s bedroom ‘half an hour after’ going to bed, adding in the letter, ‘You shall see that which shall displease you’. Caught together in an act of intimacy, Dereham was banished. According to some historians, the Duchess was more concerned with Catherine’s late-night ‘banqueting’ affecting her pretty looks than her morals. Allegedly forced to go to Ireland, Dereham left Catherine a large sum of money for safe-keeping, possibly intending to marry her after his return. Dereham’s re-emergence in her life a few years later would be the catalyst for his and Catherine’s dramatic downfall and the reason he alone would suffer the worst of a painful, unimaginably cruel and sadistic death.

Ambitious uncle

In 1539 a new exciting world opened up for 16-year-old Catherine when through astute manoeuvres by her ambitious and ruthless uncle the Duke of Norfolk, she was made lady-in-waiting to Henry’s fourth wife, the German-born and raised Anne of Cleves. It was a doomed marriage from the start when Henry took an extreme dislike to Cleves’ looks and clumsy manner and quickly looked for a get-out clause from the union after the wedding day. Catherine’s advantageous position, circulating in the same orbit as the King meant the attractive young girl soon caught Henry’s wandering eye as he distanced himself from his humiliated new bride. The disastrous royal marriage cost the life of Henry’s right-hand man and trusted advisor Thomas Cromwell, who was singularly blamed for the Cleves fiasco. Norfolk, a long-standing rival of Cromwell, seized the moment to enhance his career and that of the Catholic Howard family by parading the teenage Catherine as a possible replacement for Cleves. Once again, young Catherine was being manipulated, this time by her ambitious relatives and none more so than by her uncle the Duke of Norfolk, who three years earlier had presided over the trial of his doomed elder niece Anne Boleyn.

Thomas Culpepper: Gentleman or knave?

Thomas Culpepper was a young man all too recognisable as a shrewd type at the Tudor court. The ambitious, good looking courtier was in his late twenties, over-sure about himself and his capabilities and consciously using charm as part of his armoury. He was related to both the Howard and Boleyn families and was described as being ‘a beautiful youth’ and a great favourite of King Henry. Catherine fell for the gallant and sexually experienced Culpepper after becoming acquainted with him in the King’s Privy Chamber. Her early feelings may have been more to do with infatuation but by the autumn of 1539, she had fallen genuinely in love with him. Whether Culpepper felt the same way is not known but as Catherine became smitten with the 25-year-old a more momentous event was to change Catherine’s life when the King himself become besotted with the young lady-in-waiting.

Dangerous past

Catherine’s uncle and the rest of the Howard family made the most of their good luck when Henry fell for the Duke’s 17-year-old niece. Although Norfolk had planned for this outcome, Catherine was not an ideal candidate. Her unsuitability had little to do with the fact she had sexual history, as many young girls of the time had similar experiences. The main problem was that Catherine had been in some form ‘precontracted’ to Francis Dereham making any attempts to put her forward as the next bride for Henry not only illegal but treasonable if discovered.

If members of the Howard and Norfolk families were privy to this information they certainly kept the matter conveniently forgotten for Catherine had unexpectedly become the golden goose, with the potential to change the fortunes of the Howards and the Duke of Norfolk himself. Catherine’s step-grandmother, the Duchess, even began coaching her on ‘how to behave to the King’ as his passion grew. What members of the Howard family and employees of Chesworth House, notably the Duchess had forgotten was how serious the consequences would be for them if they were found to have purposely concealed knowledge of Catherine’s sexual behaviour, and more importantly, the existence of a pre-contract.

The First victim: Thomas Cromwell

Henry revealed his intention to marry the teenage Catherine when he granted lands to ‘Mistress Howard’ on 14 April 1540. She also received twenty-three gifts of quilted sarcenet (luxurious fabric used as lining material) from the King. It is believed that shortly afterwards, the king had sexual relations with the now 17-year-old Catherine while he was still technically married to Queen Anne of Cleves. By May, Henry had tired of the slow pace of divorcing his German wife, particularly as there was a chance Catherine had become pregnant. On May Day celebrations the royal marriage was annulled due to non -consummation, an event which also saw the arrest of Thomas Cromwell on charges of heresy and who was sentenced to death by an Act of Attainder with no trial.

Cromwell was the first to die by a technicality he had himself created to execute others. Lady Cleves, having played the game wisely and massaged King Henry’s ego by appearing to be a good submissive wife to his commands, was rewarded with a handsome settlement of stately homes and estates for a lifetime. On 28 July, the same day Thomas Cromwell was publicly executed on Tower Hill, Henry married Catherine. Although the teenage bride vowed to be ‘bonair and buxom in bed’ what she didn’t reveal was that this sensual promise also included her secret lover Thomas Culpepper. It was a dangerous game with a short fuse that would lead to an explosive climax of trauma and violence.

Rich man’s jewel

The rejuvenated King lavished affection on his young wife, who he had been led to believe had been a virgin when he married her and showered her with rich gifts while often referring to her as his ‘rose without a thorn’. Such attention must have been overwhelming for a young girl who had been brought up as a poor relation to the grandees in her own family and was now in a position to make them richer and more powerful. As her new glamorous world continued to dazzle her with a stream of magnificent jewels and expensive ornaments, as well as being granted the castles, lordships and manors that had belonged to Henry’s third wife Jane Seymour, danger was lurking in the form of Francis Dereham. He was back not just in England but at the royal court itself, possibly in a job handed to him by the Duchess to keep him quiet about past indiscretions.

This arrogant and indiscreet young man had been given the role of ‘secretary’ to Catherine, a dangerous move that took great risk to keep Dereham’s boastful mouth shut. Meanwhile, King Henry paraded Queen Catherine like a rich man’s jewel at banquets and celebratory events to show the world that he was still a virile monarch in love and lust with a nubile young bride.

Fatal attraction

Despite King Henry’s lust for his young Queen, he was by now in the summer of 1540 an increasingly obese and ill man with a 54-inch waist. It was at this time that a new suit of armour was specially commissioned for him that was customised to fit his increasing corpulence with a somewhat over-generous steel codpiece. Worse for Henry’s health, mobility and temperament were the painful varicose ulcerations of his legs which became chronic. As the inflamed veins became thrombosed, resulting in swelling of the lower legs, Henry suffered regular bouts of fever causing the King to display rage and frustration beyond his usual displays of daily irritation. This vicious circle of pain and ill health meant Henry could be confined to his quarters, separating him from Queen Catherine for long periods.

During the spring of 1541 when Henry suffered an agonising attack of swollen suppurating legs, was a period when a neglected Catherine may have decided to indulge in what to her appeared to be just light-hearted flirtations with Thomas Culpepper, a man she had developed amorous feelings for before she married King Henry.

Playing with fire

Whether clandestine meetings between the Queen and Culpepper resulted in sexual activity before March 1541 is not known, but when a much recovered Henry decided to take his wife with him on a northern tour, culminating with a planned coronation of Catherine in York, Culpepper, in his envied position in the King’s Privy Chamber also went with the entourage. If Culpepper’s decision to become intimate with Queen Catherine appears not just merely rash but insane considering the potential dangers, his thinking may have been influenced by more far-sighted reasons. There were rich pickings for a young man like Culpepper to be a favourite of the Queen, while her husband Henry was alive and possibly even greater ones after he died. The fact Henry was beset with ill health and of an advancing age meant that Catherine as a Dowager Queen would have a great deal to offer an ambitious man who was her true lover.

Henry’s northern progress during that spring had political aims, mainly to show his dominating presence in a part of the country known for rebellious insurrections. What Henry wasn’t aware of while the royal tour made its way to Pontefract, York and Hull was another form of rebellion that was taking place, that between his wife and Thomas Culpepper, whose clandestine late-night trysts were being facilitated by one Lady Jane Rochford, one-time sister-in-law of the doomed Anne Boleyn.

Whatever Lady Rochford’s motivations were for taking such risks to act as a look-out and go-between for the two lovers, neither of the trio had any idea that back in London, rumours about Catherine’s past indiscretions at Chesworth House had now reached the ears of the Archbishop of Canterbury.

Scandalous rumours

What prompted characters associated with Chesworth House, where Catherine had been a teenage ward, to approach Archbishop Cranmer with details about the young Queen’s colourful past is not known for certain. But one John Lascelles came armed with startling information relayed to him by his sister, Mary Hall, who was a chamber woman to Dowager Duchess Agnes who had disapproved of Catherine’s behaviour while she was staying at Chesworth. Damning details included salacious stories about Catherine and sexual activities with Francis Dereham, but more importantly, the alleged precontract. Another witness to what went on in the Sussex house was in the form of Margaret Benet, who told Cranmer when interviewed by him that she ‘looked through a hole in the door’ and saw Catherine and Francis Dereham having sex. 'Her clothes were above her navel and I saw her naked body' confessed Benet adding that Dereham said to Catherine, '...although he used the company of women, he would not get her pregnant'. Catherine, according to Benet, is alleged to have replied, 'A woman may meddle with a man and not conceive.'

The witness admissions from Benet and Mary Hall were seen as proof that Queen Catherine was no virgin when she married the King, but more seriously that she knew of her status at the time of marriage, a fact that was treasonous.

Investigation and torture

On 2 November 1541, the now 50-year-old Henry was taking mass in his private chapel at Hampton Court when he came across a letter secretly left for him under a seat. The letter was from Archbishop Cranmer and its contents were explosive. Detailing Queen Catherine’s sexual past at Chesworth, Henry initially dismissed the letter’s accusations of his wife’s promiscuity as vicious lies. After the tribulations of Anne Boleyn’s downfall due to alleged adultery, it was difficult for him to believe that he had been betrayed again. But the shocking allegations of ‘immoral living’ at Chesworth prompted Henry to agree to investigations on the quiet. Henry was emotionally devastated by Cranmer’s news and on returning to his private chambers broke down in tears.

Soon afterwards Francis Dereham was arrested and tortured, most likely on the rack, at the Tower. In horrendous pain, he confessed that he had been Queen Catherine’s lover but denied he was still having sex with her, even though he had been given a position at court near to her.

During the torture, Dereham dropped a bombshell that would condemn Catherine further, revealing that Henry’s most trusted advisor and friend, Thomas Culpepper, was having relations with her. This revelation was more shocking because of the intimacy Culpepper had with the King, he would even dress and undress the monarch and at times sleep in his private chambers.

Culpepper was arrested and like Dereham brutally tortured. As the truth emerged the King’s ‘perplexity’ and desperation not to believe the accusations gave way to an orgy of self-pity. Blaming his Council and others for this devastating state of affairs his mood turned to anger at the Queen’s ingratitude and what he felt was a monstrous betrayal. He called for a sword to slay her and in a momentary state of rage vowed she should be tortured, before breaking down with more tears. Pride was the main victim here, as Henry felt once again he had been cuckolded and made to look a fool in the eyes of the world, this time by a teenage girl. Investigations continued to seal Catherine’s fate.

Evidence of betrayal: The love letter

The damning evidence of the illicit relationship between the Queen and Culpepper was found in a letter to him, which displayed tenderness and the kind of love a woman would have for a man she could not always be with. The letter, discovered in Catherine’s private chambers had been written in April 1541. It was a love letter to Thomas Culpepper, the only one of Catherine’s letters to survive, and provided evidence of a relationship that was not only adultery but also potentially threaten the Tudor bloodline. Had Catherine become pregnant by Culpepper, she could have passed the child off as Henry's. The first eighteen words of the letter appear innocuous enough before Catherine’s prose demonstrates a more passionate tone: ‘I would you were with me now that you might see what pain I take in writing to you’.

Her concern for her lover’s health is evident. ‘I heard you were sick and never longed so much for anything as to see you’, ending with unmistakable passion for Henry’s once trusted courtier. ‘It makes my heart die to think I cannot be always in your company’. The letter is signed with heartfelt emotion ‘Yours as long as life endures – Katheryn’.

It was as good as a death warrant.


Archbishop Cranmer took it upon himself to interview Catherine, where his account of his conversation with her makes pitiful reading as the man himself was moved by the emotional distress the young girl was suffering. ‘It would have pitied any man’s heart in the world, to have looked upon her’ wrote Cranmer after he had witnessed her behaviour and mind as that of being in a ‘frenzy’. At first, Cranmer believed Catherine’s ‘precontract’ to Dereham would make Henry’s marriage to Catherine invalid, meaning at most she would simply be disgraced. But more witness statements, including that of Lady Jane Rochford, painted a more serious picture of Catherine and Culpepper’s love affair taking place, usually at night in places which included Greenwich, Lincoln, Pontefract and York. Lady Rochford attempted to present herself as an innocent bystander who was unaware of what was going on, while Catherine herself countered Rochford’s statements by describing her as a knowing facilitator who tempted her with seductive notions of dalliance with Culpepper.

On 24 November 1541, the Council formally demoted Catherine’s title of Queen and indicted her for having led ‘an abominable, base, carnal, voluptuous and vicious life’ before marriage, while maintaining ‘the outward appearance of chastity and honesty’. In other words, she had tricked the King into loving and marrying her and concealed the precontract she had with Francis Dereham. The seriousness of the last count was seen as a threat to the King with the possibility that any children she had with him could have been bastards. The fact that Catherine had instigated a love affair with Henry’s close aide Thomas Culpepper, could have also rendered the Queen pregnant and equally threatened the royal lineage which amounted to one thing – an unquestionable case of treason. Along with Francis Dereham, Thomas Culpepper and Lady Jane Rochford, the Queen was condemned to death by an act of Parliament.

The Executions

Both Thomas Culpepper and Francis Dereham were taken by cart from the Tower and through the streets of London to Tyburn, where after Culpepper made an exhortation to the crowd to pray for him was quickly beheaded as a terrified Dereham looked on, fearing the worse fate in store for him.

If anyone doubted the potential savagery of Henry VIII, few examples illustrate his penchant for cruelty than the barbaric death he chose for Dereham, simply because as a reckless youth he had ‘spoiled’ Queen Catherine for him. The fact that Dereham had sexual relations with the young Catherine before she even became known to King Henry was of little consequence. Dereham like Culpepper had earlier petitioned King Henry to commute his sentence to beheading but was refused. Instead, he was subjected to the inhuman execution of a ‘traitor’s death’, that of being ‘hung, drawn and quartered’.

Seconds after Culpepper’s head had been smitten from his neck, Dereham was strung up on a gibbet, hung for several minutes and cut down while still alive. His writhing body was dragged to a board where placed belly-up he was brutally disembowelled by the executioner. Still conscious, his stomach was sliced open and his internal organs were wrenched out from his body. The hideous spectacle ended with castration and finally beheading. Both men’s heads were stuck on spikes on London Bridge.

Several people had also been taken into the Tower in connection with the scandal, their crime was ‘misprision of treason’ relating to their advance knowledge and concealment of the secrets of Catherine’s past. The prisoners included Catherine’s step-grandmother, Duchess Agnes and other Howard family members. Surprisingly Thomas Howard, Duke of Norfolk who was Catherine’s uncle and who had masterminded his niece’s journey from a ward of Chesworth House into the bed of King Henry, was not amongst the arrested. His cunning nature along with a grovelling letter to the King blaming his niece and the Duchess, not only saved him but paved the way for his continuing occupation in the Tudor court. Catherine’s relatives were originally sentenced to life imprisonment but in time later released.

Catherine had been transferred to Syon Abbey (now House) in Middlesex during a bitterly cold December in 1541, before waiting for her execution at the Tower. Knowing of Culpepper’s death she was to spend nearly two months in moderately furnished rooms and with servants rather than jailers. On 10 February 1542, the once royal prisoner was transferred to the Tower by a small sealed barge. It was reported that the enormity of her fate suddenly hit home as she became hysterical and had to be forced on board. On reaching the Tower, Catherine may have seen the boiled heads of her lovers Dereham and Culpepper on London Bridge as her boat went under it. The following day Catherine was informed she was going to die on the 13 February at seven o'clock. Lady Jane Rochford was poised to end her life on the same scaffold after Catherine’s execution.

Rehearsal for death

What has now become a legendary part of her tragic story and last hours on earth was when Catherine requested that the executioner’s block be brought to her rooms, so that she may practice her death with grace and dignity. The next morning on 13 February 1542 Catherine, said to look pale and terrified was, according to the French Ambassador, ‘so weak that she could hardly speak’ and had to be assisted to the scaffold. She managed to confess a few words, praising the King for having treated her so graciously before she was blindfolded and quickly beheaded. Lady Jane Rochford, standing on the same scaffold on Tower Green showed less bravery as she became hysterical and was pushed to the block, freshly stained with the blood of Catherine and quickly dispatched.

Catherine Howard who had only been Queen for eighteen months was executed on the same block and place as her cousin Anne Boleyn less than six years earlier. Like her tragic cousin, she was interred at the nearby chapel of St Peter ad Vincula in the Tower.