Mistress Skipwith - a possible candidate for the King's wife?

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One of the most well-written attributes of King Henry VIII was his infamous penchant for mistresses. Although numbering nowhere near as high in comparison to his overseas rival King Francis I, Henry VIII nonetheless, at almost any given period, was entertaining an extramarital affair. Some of these women and their tenure within the king’s Chamber are considerably well-documented, most infamously Elizabeth ‘Bessie’ Blount. On the other hand, some female courtiers are only briefly mentioned as having caught the king’s eye, such Lady Anne Stafford; leaving their relationship with Henry down to considerable interpretation. More so, hardly any information is given at all, leaving us to question if they even had an extramarital relationship. One of such women was Lady Mary or Margaret Skipwith, who we will be discussing in this post.

Lady Mary/Margaret Skipwith was born in around 1520 to Sir William Skipwith of Ormsby and Alice Dymoke, hailing from Lincolnshire gentry. With close connections to court from her family seat, Margaret, as she will be entitled for the purpose of convenience, likely would have entered the royal court shortly following her coming of age at around thirteen years old. No mention of Margaret survives until January 1538, when John Husee sent a letter to his overseas employer Lord Lisle, preserved in the Lisle Letters. Arthur Plantagenet, 1^st Viscount Lisle, by this time was appointed Lord Deputy of Calais. As a result, Lisle was situated in the heart of the European continent during the time Henry VIII was seeking his fourth wife: to be made aware of what kingdoms or principalities Henry was desiring to negotiate a match with would have been vital. In his letter to Lisle concerning Henry’s matrimonial choices, John Husee wrote that: ‘The election lieth betwixt Mrs Mary Shelton and Mrs Mary Skipwith. I pray Jesu send such one as may be for his Highness’ comfort and the wealth of the realm. Herein I doubt not but your lordship will keep silence till the matter be surely known.’

It is particularly interesting that both ladies addressed in this letter hail from the English court, rather than overseas. Just a few short months after the death of his third wife Jane Seymour, this letter indicates that Henry had already sought comfort in the arms of another: either his previous alleged mistress Mary Shelton, or a new woman – Margaret Skipwith. However, it would be unwise to suggest that a torrid affair equated to a potential marriage prospect. It was around this time that Henry VIII had began to contemplate marrying, and as we know with the benefit of hindsight, he wished to found his latest marriage on political benefit and overseas alliance. What this does tell us is that whilst it would be made evident that Henry’s fourth queen would be a foreign noblewoman, for a time it was assumed that she would be another Englishwoman. In this case, that woman possibly being Margaret Skipwith.

Just as is the case with other Tudor women immortalised in document, discrepancies in palaeography have led to confusion surrounding her exact identity. The same occurs with the aforementioned Mary Shelton, Henry’s reputed mistress in 1535. Some confusion still exists as to whether Mary, as she is assumed to be called, was instead meant to say ‘Marg,’ a common nickname for ‘Margaret’. Whilst most scholars, myself included, concur that Henry’s mistress was indeed a Mary Shelton, it is likely that Husee was referring to Margaret rather than Mary Skipwith. Margaret Skipwith did have a sister by the name of Mary, though it is unlikely she was his mistress. In 1550, Mary Skipwith married George Fitzwilliam of Mablethorpe. In that case, it would be illogical to assume Mary had a relationship with Henry due to being too young. Nonetheless, Elizabeth Norton argues that Fitzwilliam’s date of birth remains unclear, as does the exact timing of the births of their eight children. In that case, it could be plausible that Mary was indeed Henry’s mistress, albeit a young one.

Unlike her sister Mary, Margaret Skipwith remained at court for the remainder of Henry VIII’s reign. As a member of the royal court, Margaret likely exceeded in all the skills necessary to remain at the court for an extended period of time, such as attending on the queen, instruments, reading and embroidery. Margaret was present in August 1539 on a trip to Portsmouth, with the purpose of seeing the king’s naval fleet. In a letter, alongside ten other ladies, Margaret thanked the king for arranging the excursion. Although not present, they praised the king and his ships, which were ‘so goodly to behold that in our lives we have not seen a more pleasant sight.’ According to a biography of her second husband, Peter Carew, Margaret was present for the formal welcoming of Anna of Cleves from Calais alongside her husband George Tailboys. This invites us to investigate an interesting link between Margaret Skipworth and another infamous royal mistress, Bessie Blount. In April 1539, Margaret Skipwith’s uncle Sir Thomaas Heneage confirmed in a letter to Thomas Cromwell that the king had given the all-clear to orchestrate a marriage between Margaret and the teenage George, Lord Tailboys. Tailboys was the son of Bessie Blount and Gilbert Tailboys, who Blount was married off to in swift succession after her tenure in the king’s bed ended. Margaret’s case closely mirrors that of Bessie’s, with the king commanding Heneage to arrange the marriage as quickly as possible, indicating that he wished for the matter to be concluded swiftly. By the end of that same month, Husee once again mentioned Skipwith in a letter to Lord Lisle: ‘it hath been shewed me that Mrs Skipwith shall marry the Lord Tailboys.’

On the 15^th May, Skipwith was briefly mentioned as being married to Tailboys. Despite the fact that it was mentioned without further comment, it is notable that Husee thought to mention it to his master in the first place: evidently, news concerning Margaret and Henry’s relationship had become common knowledge outside the court environment.

Similarly to his other mistresses, Henry guaranteed Margaret a number of financial and societal protections on the occasion of her marriage. One such example was an Act of Parliament, in which Tailboys’, who had yet to reach adulthood’s, wardship was gifted to Margaret’s kinsman, the Earl of Southampton. As a result of the act, Margaret and her husband were given considerable financial flexibility to arrange their estates and jointures as they wished, making the arrangement of their newlywedded life significantly easier. In accordance with the same laws bestowed upon his father Gilbert, George was able to circumvent usual laws concerning the inheritance of his estates. George and Margaret were then able to purchase numerous manors in Lincolnshire, as well as accede to his lands in Somerset. Whilst these benefits were in accustom with her husband’s own birthright, it is likely that Margaret’s role as Henry’s mistress provided them with favour and an extra security blanket as they began to charter married life.

Shortly after their marriage, in 1540, Tailboys passed away in his late teens. However, Margaret continued to reap the benefits of her royal and courtly connections, all the while acting as a landowner in her own right. In 1543, Margaret was granted the wardship of one Charles Toffoft, from Lincolnshire landowners. It would not be until 1546 that Margaret would wed again, when she married Sir Peter Carew. Margaret continued to call herself Lady Tailboys however, in accordance with the superior social ranking of her deceased husband. Carew would soon become embroiled in scandal as one of the chief architects of the 1554 Wyatt Rebellion, narrowly escaping the executioner’s block.

Margaret’s life thereafter became burdened with her husband’s disgrace. It is reputed that Margaret, at one point, pleaded to Mary I’s council for her husband’s pardon. To escape a spell in the Tower, Carew spent years fluctuating around Europe – spanning from Venice, Brussels to Strasbourg. This led to Carew accumulating significant debts, owning the crown £820 by 1556. As she was a landowner in her own right, as well as overseeing land left to her by Tailboys, Margaret spent most of her days in Lincolnshire and Somerset. In 1579, Margaret would once again marry to Sir John Clifton of Barrington, but as with her other two marriages, they would be unfruitful. The burden of her second husband overshadowed Margaret by the time of her death in May 1583, with his crippling debts still owed to the crown.

Without ceremony or pomp, Margaret Skipwith died in the same way many of King Henry’s other mistresses did. Whilst the remainder of her final years were spent navigating the tribulations of landowning, exertion and inherited scandal, Margaret had at one point almost been the talk of Europe. Whilst it remains unclear how long her relationship with Henry VIII lasted, what the nature of their bond was – or how long it even lasted – one thing remains certain. If tides had shifted differently, if passion and desire had overcome political ambition, if Margaret Skipwith had been as ambitious as her other English predecessors, she may have been Henry’s fourth queen.

References:

1. Hart, Kelly, The Mistresses of Henry VIII, (The History Press, 2015)

2. St Clare Byrne, Muriel, The Lisle Letters, (Chicago, 1981)

3. The Anne Boleyn Files, Norton, Elizabeth, Margaret Skipwith of Ormsby: Mistress of Henry VIII, (2014), Accessed at: https://www.theanneboleynfiles.com/margaret-skipwith-ormsby-mistress-henry-viii-elizabeth-norton/  

4. Tudor Place, Margaret Skipwith, Accessed at: Margaret SKIPWITH (B. Talboys of Kyme)