Margaret Skipwith of Ormsby: Mistress of Henry VIII by Elizabeth Norton

Posted By on February 25, 2014

Elizabeth Norton

Elizabeth Norton

Thank you so much to author and historian Elizabeth Norton for writing this guest post on Margaret Skipwith. Over to Elizabeth…

Henry VIII’s love life was notoriously complicated although, unlike most of his royal contemporaries, he tended to marry women who would otherwise have been only his mistresses. The death of Jane Seymour in October 1537 left him without an immediate candidate for a fourth wife. For a few brief months in 1538, it looked as though his choice had fallen on the almost unknown Margaret Skipwith of Ormsby.

Margaret was first tentatively suggested as a possible mistress of Henry VIII’s in the 1980s, but it has never been considered in detail before.

Mary or Margaret Skipwith?

Direct evidence of Margaret’s affair with Henry VIII is scant. In a letter of 3 January 1538 to his employer, Lord Lisle, John Husee, who was resident at court commented 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”.1

Muriel St Clare Byrne, in her commentary on the Lisle letters, suggested that the recently widowed king, who was already searching for a fourth bride, was casting an appreciative eye on both ladies, looking to make one of them either his mistress or his wife.2 This is very probable. Mary Shelton, who was referred to in the letter, was a cousin of Anne Boleyn. There is some confusion over her identity, since both Margaret and Mary Shelton were resident at court and the name Margaret, when written as an abbreviation, resembles Mary. A ‘Madge’ Shelton, who is generally identified as Margaret, had already filled the role of royal mistress during the king’s marriage to Anne Boleyn. It may be that the Mary Shelton of January 1538 was the second sister or, more probably, both ladies were the same (whether actually Margaret or Mary). Henry VIII’s interest in Mistress Shelton in 1538 was widely known, with his ambassador to the court at Brussels commenting of Christina of Denmark, whom the king was hoping to marry, that she resembled the English lady.

There is some evidence that it was Mistress Skipwith, rather than Mistress Shelton, who succeeded in winning Henry VIII’s affections. In his letter, John Husee identified Mary Skipwith as the subject of the king’s interest. Like the Sheltons, there were also two Skipwith sisters named Mary and Margaret who could be identified as the lady. The sisters were the daughters of Sir William Skipwith of Ormsby and his second wife, Alice Dymoke.3 They came from a solid Lincolnshire gentry family.

The lady in question is usually identified as Margaret Skipwith, but is this correct? In a recent study, it was claimed that it was likely to have been Margaret rather than Mary since Mary married George Fitzwilliam of Mablethorpe around 1550, suggesting that she was too young to have been considered as a potential royal mistress or bride in 1538.4 Evidence however suggests that the 1550 date is wrong.

Mary’s husband, George Fitzwilliam, was described as aged over thirty in the Inquisition Post Mortem taken for his father, John Fitzwilliam of Skidbrook in August 1547, suggesting that he was born in c.1517.5 Mary Skipwith bore her husband four sons and four daughters. In his Will dated 13 January 1560, her husband named all eight of the children, with the eldest son, William described as being under the age of twenty-one.6 None of the daughters were then married, although the eldest, Frances, was betrothed, with the terms of her father’s Will implying that the marriage was imminent, something that would suggest that she was already approaching, or over, fourteen – the age of consent for girls. While it would have been just possible for Mary Skipwith to bear her husband eight children in ten years of marriage, given the likely older age for Frances in 1560, coupled with high infant mortality in the sixteenth century, it is improbable. This pushes the date of Mary’s marriage back some years earlier than 1550.

This can also be seen from the surviving evidence of later generations of the family. Mary Skipwith’s eldest son, William, fathered eight children by his first wife. While the youngest was baptised in 1589, an elder daughter, Hester, was baptised on 15 May 1566.7 This suggests a birth date for her father of the early to mid-1540s. William’s daughter, Mary, married on 12 October 1590, while her sister, Bridget, may have married as early as 1587. Assuming that both women married at around twenty, this would support an earlier birth date for their father and, thus, also an earlier date of marriage for his parents. It is therefore entirely possible that Mary Skipwith was old enough to be considered as a potential mistress or wife for the king in 1538. Mary and Margaret’s parents married in around 1520 (after the death of their father’s first wife).8 Both sisters must have been young in 1538, but, both were potentially old enough to attract the king’s attention.

The usual reason for discounting Mary Skipwith as the mistress of Henry VIII in 1538 is therefore incorrect. However, there is still strong evidence that the royal mistress was indeed her sister, Margaret. With the exception of John Husee’s letter, there is no surviving evidence to place either sister at court in 1538, but Margaret was there by at least the early months of the following year, implying a possible earlier arrival.

Margaret remained resident at court for the remainder of Henry VIII’s reign. In a sixteenth century biography of her second husband, Peter Carew, it was recorded that he first came across Margaret after returning to England from Calais where he had been sent, with her then husband, George Tailboys, to welcome the new queen, Anne of Cleves:9

“At his return home, he still continued at and about the court, being wrapped in Venus bands, and stricken with Cupid’s darts: for he had been, and was, a suitor to a lady in the court, being the widow of a baron deceased.”

Margaret remained at court following the death of her first husband in September 1540 something which suggests that she may have had long-standing connections with the court and that her presence there was not merely due to the position of her husband.

In all probability, therefore, the reference to Mary Skipwith by John Husee, in fact refers to Margaret. It is now necessary to consider the evidence for whether she can be considered to be one of Henry VIII’s mistresses.

Mistress to Henry VIII

Henry VIII

Henry VIII

For a sixteenth century king, Henry VIII took few mistresses. The two most well-known, and longest lasting, affairs were with Bessie Blount and Mary Boleyn early in the reign. Bessie Blount makes a particularly interesting point of comparison with Margaret Skipwith as, when the king had tired of her, he arranged for her to marry Gilbert Tailboys of South Kyme. Less than twenty years later, Margaret Skipwith was married off to Elizabeth Blount’s son, George Tailboys.

The strongest evidence that Margaret Skipwith was a mistress of Henry VIII’s is found in the arrangements made for her first marriage. The affair obviously only lasted a few months, with the king taking steps to marry Margaret off quickly. On 17 April 1539, Margaret’s uncle, Sir Thomas Heneage, wrote to Thomas Cromwell to confirm that the king had given his consent to a match between Margaret and the sixteen year old George, Lord Tailboys. Tellingly, the king commanded Sir Thomas that it would be well to have them married as soon as possible, something that suggests that he was anxious for matters to be concluded.10 Arrangements were made with some secrecy, with John Husee informing his master on 26 April 1539 that “it hath been shewed me that Mrs Skipwith shall marry the Lord Tailboys. This it shall please your lordship to keep secret till you hear more”.11 The reason for this secrecy, or even Lord Lisle’s interest in the match, is pertinent, particularly as on 15 May 1539 Husee deemed it important enough to inform Lady Lisle that “the Lord Tailboys is married” with no further comment.12 The suggestion must be that Margaret, as the king’s most recent love, was newsworthy.

St Clare Byrne speculated that the reference to Margaret Skipwith as a potential love interest for Henry, coupled with the king’s interest in her marriage and the secrecy with which it was conducted “perhaps justify the suspicion that the youthful George was happy to follow obligingly in his father’s footsteps for the sake of an attractive young wife and the enjoyment of his own inheritance at sixteen, instead of having to wait until he was out of wardship at the age of twenty-one”.13 This is highly probable, as the evidence of George’s parents’ marriage shows.

In 1517 the lands of Gilbert Tailboys’ father, George, were placed in the custody of Cardinal Wolsey and eight trustees on account of “the said Sir George being a lunatic”.14 Gilbert, who had by then reached his majority, but had no position in society given his father’s continued survival, passed into the Cardinal’s custody at the same time as a member of his household. He was therefore very conveniently placed in early 1522 when the king decided to discard Bessie Blount, a woman who had borne him a son and, perhaps, also a daughter during an affair that had lasted approximately five years.15 Gilbert’s price was freedom and, within a few months of his marriage, he was able to act largely free of the Cardinal’s influence in Lincolnshire, building his own powerbase.16 He may also have sat in parliament that year. He was certainly a member of parliament by 1529, in the year that he was also created Baron Tailboys of Kyme.17

In addition to this, Gilbert and Bessie received grants of property from the king, such as the manor of Rugby as a wedding present.18 More significantly, they were given access to Gilbert’s inheritance, in spite of his father’s continued survival. In 1523 an Act of Parliament was passed in Bessie’s favour, ostensibly following a petition by Gilbert and his father, the incapacitated Sir George:

“Humbly shewith unto your most excellent Highness your true and faithful subjects and servant Sir George Tailboys Knight and Gilbert Tailboys son and heir apparent to the said Sir George, That where the said Gilbert hath married and taken to wife Elizabeth daughter of John Blount Esquire, by which marriage as well the said Sir George Tailboys Knight as the said Gilbert Tailboys have received not only great sums of money, but also many benefits to their right much comfort. In consideration whereof and for the great love favour and affection that as well the said Sir George Tailboys as the said Gilbert Tailboys his son have and toward the said Elizabeth, your said Oratours most humbly beseecheth your Highness that by the assent of the Lords Spiritual and Temperal and the Commons in this present parliament assembled and by authority of the same, to ordain establish and enact that the said Elizabeth may have hold and enjoy for terms of her life natural without impeachment of any waste this Lordships Manors Lands Tenements and Hereditaments hereafter ensuing which be of the inheritance of the said Sir George Tailboys”.19

Bessie received a life interest in Tailboys lands in London, Lincolnshire, Yorkshire and Somerset. The grant enriched Gilbert and Bessie at his parents’ expense, with the value of Gilbert’s lands rising rapidly during the 1520s from £66 13s. 4d. to £343: a vast increase given that his father was still very much alive.20 In addition to this, the claim that Gilbert and his father “have received not only great sums of money, but also many benefits to their right much comfort” from the marriage hints at the negotiations that must have gone on between Wolsey, the king and Gilbert in order to secure the young man’s consent to his marriage. That these grants were solely for the benefit of Gilbert and Bessie are clear from surviving letters written by Gilbert’s mother complaining that the couple were attempting to put pressure on her and her incapacitated husband to relinquish further lands, with the elder lady’s suspicion being that her daughter-in-law was directly making suit for them with the king at court.21 Bessie Blount was well rewarded for her relationship with Henry VIII.

Matters followed a similar pattern with her likely predecessor as the king’s mistress, Elizabeth Carew, who later wrote that “all that I have had in my life hath been of his grace, and I trust that his grace will not see me lack; but whatsoever his grace or your lordship shall appoint me, I both must and will be content”.22 The estates mentioned by Elizabeth Carew in her letter written after the execution of her husband, Sir Nicholas Carew, in 1539, had been settled on the couple by the father-in-law at the time of their marriage.23 It appears that it was common for the king to provide for a former mistress through grants from her new husband’s family estates. This can be paralleled in the case of Margaret Skipwith.

Soon after her marriage to Bessie Blount’s son, Margaret’s financial future was safeguarded by an Act of Parliament, which recited that the king was in possession of George’s lands during his minority and that he had granted his wardship to Sir William Fitzwilliam, Earl of Southampton. According to the Act, the king, at the request of the earl, who was a kinsman of Margaret’s, and in gratitude towards the “good and faithful” service given by Gilbert Tailboys, had:

“Pondered and considered that the said George now lord Tailboys hath not ne can have by the order of his laws any part or portion of the rents or profits of his said inheritance to support and maintenance of his convenient and reasonable living during his said minority, but only by the appointment and assignment of his said most gracious highness; and also considering that the said George lord Tailboys, by the order of his said laws, during his said minority cannot make any effectual feoffment, ne estates or jointure, to the said now lady Margaret, wife to the said George lord Tailboys, towards her necessary living.”24

As a result of the Act, George and Margaret were granted the use of a number of their Lincolnshire manors, as well as Tailboys lands in Somerset. George, like his father, was, by his marriage, able to circumvent the usual laws governing inheritance in order to enter into estates before they were due to him. This Act of parliament, like the earlier Act made for the benefit of Bessie Blount and the grants to Elizabeth Carew suggest that Margaret Skipwith, like her mother-in-law before her, received a rich marriage as her reward for an intimate relationship with the king.

Margaret Skipwith and Henry VIII

Although no details of the actual affair survive, Margaret remained in high favour with the king, a position that parallels the respect in which her mother-in-law, Bessie Blount, continued after the ending of her own affair with Henry VIII. At New Year 1541, Margaret was one of a select number of favoured ladies who gave the king a gift, with her servant receiving 13s. 4d. for his pains, the same sum that had been given to Bessie Blount’s servant for delivering a gift in 1529.25 While details of the gifts made by the king do not survive, it is highly probable that he reciprocated. Lists of Henry VIII’s New Year’s gifts are fragmentary, but it is clear that he often honoured former mistresses with a present.26 In addition to this, on 16 June 1543, Margaret was granted the wardship of Charles Tottoft, the son of a substantial Lincolnshire landowner, taking custody of the boy’s lands until he came of age.27 It may be Margaret to whom the king’s letters were directed in 1546, for which a receipt survives confirming that they were addressed to “Lady Talboys”.28

Further evidence that Margaret Skipwith was the king’s mistress can be found with regard to Peter Carew’s courtship of her. When the widowed Bessie Blount was courted by Lord Leonard Grey in 1532, her suitor petitioned Thomas Cromwell to ask the king to intervene on his behalf.29 He also took steps to ascertain that the king would not be displeased if he proposed marriage to Bessie.30 A very similar approach was followed by Peter Carew, whose suit was met as lukewarmly by Margaret as Grey’s was by Elizabeth. According to his biography, Carew attempted for some time to woo Margaret:

“But having used all the means he could to obtain his purpose, and minding not to have the repulse, he went unto the king, and opening unto his grace his suit, did most humbly beseech his highness to stand his good lord. The king at first seemed to strain courtesy at the matter, neither would have any good liking thereof: nevertheless, in the end, he did so consider of the worthiness and nobility of the gentleman, that he did not only grant his request, but also wrote his most earnest letters unto the lady in his behalf, and promised also to give with that marriage a hundred pound land to them and to the heirs of their bodies”.31

Henry’s intervention and his promise to dower Margaret suggests a connection between the pair.

While no portrait of Margaret survives, given Carew’s affection for her and her evident relationship with the king, she must have been attractive. As a member of the court, she is also likely to have been accomplished. In a letter written on 4 August 1539 Margaret, along with a number of other court ladies, wrote to Henry VIII to thank him for arranging a trip for them all to see his fleet at Portsmouth.32 The ladies were able to assure the king that, whilst they were disappointed that he had not been present, the ships were “so goodly to behold that in our lives we have not seen (excepting your royal person and my lord the Prince your son) a more pleasant sight”. The king laid on entertainments and gifts for the ladies and invitations to the event must have been highly sought after. The fact that Margaret was one of the ten women invited to attend hints strongly at her close relationship with the king. When Henry’s fourth wife, Anne of Cleves, arrived in England at the end of December 1539, Margaret was one of the ladies appointed to receive her.33

Margaret Skipwith: Mistress to Henry VIII

The evidence strongly suggests that it was indeed Margaret Skipwith to whom John Husee referred in his letter of 1538 and that, in the months that followed, she was involved in a love affair with the king. If John Husee’s comments are reliable, it appears that Henry VIII even considered making Margaret his bride, as he would do with four other Englishwomen during his reign. If circumstances had been different, Henry VIII’s fourth wife could have been comely Margaret Skipwith rather than the disappointing Anne of Cleves.

Elizabeth Norton has her own blog – http://elizabethnortonhistorian.blogspot.co.uk/ and has written several books, including biographies of four of Henry VIII’s wives, biographies of Margaret Beaufort and Bessie Blount, and The Boleyn Women.

  1. The Lisle Letters, V vols, St Clare Byrne, M., ed. (London, 1981) vol V n.1086
  2. Ibid., pp11-13
  3. Cook, R., The Visitation of the County of Lincoln in 1562-4, Metcalfe, W.C., ed. (London, 1881)
  4. Hart, K., The Mistresses of Henry VIII (Stroud, 2009)
  5. Massingberd, W.O., History of the Parish of Ormsby-Cum-Ketsby in the Hundred of Hill and County of Lincoln (Lincoln, 1991)
  6. The National Archives, PROB 11/43: Will of George Fitzwilliam Esquire of Mablethorpe
  7. Maddison 1902
  8. Maddison, A.R., Lincolnshire Pedigrees, vol III (London, 1904) and Monumental Inscriptions in the Church of Beakeby, Lincolnshire’ in The Topographer vol I number III, 1789:113-116)
  9. Hooke, J., The Life and Times of Sir Peter Carew, Maclean, J., ed. (London, 1859:15)
  10. Letters and Papers, Foreign and Domestic, of the Reign of Henry VIII, Vols I-XXI, Brewer, J.S., Gairdner, J. and Brodie, R.H., eds. (London, 1862-1932). L&P XIII pt I 795 (Sir Thomas Hennege to Cromwell, 17 April 1538)
  11. Lisle Letters V 1394
  12. Lisle Letters V 1414
  13. Lisle Letters V p12
  14. Richardson, W.C., The Surveyor of the King’s Prerogative (English Historical Review 56, 1941:60), TNA C142/31/41 and L&P I 2979.
  15. Norton, E., Bessie Blount (Stroud, 2011)
  16. L&P IV pt I 390, 819, 1795, 2002, L&P IV pt II 5083, L&P III pt II 3282 and 3504 and L&P III pt II 3583
  17. L&P IV pt III 6042
  18. L&P III pt II 2356
  19. Statutes of the Realm, vol III (London, 1817)
  20. Bindoff, S.T., The House of Commons 1509-1558, vol III (1982:419)
  21. Elizabeth, Lady Tailbois to Cardinal Wolsey, 11 June 1528 (West Yorkshire Archive Service WYL 230/3788) and Elizabeth, Lady Tailboys to Mr Thomas Heneage, 1 April 1529 (Wood, M.A.E. (ed.), Letters of Royal and Illustrious Ladies, 3 vols: vol II pp43-45)
  22. Elizabeth, Lady Carew, to Lord Cromwell, 1539 (Wood 1846, vol III pp110-111)
  23. Mitchell, R., The Carews of Beddington (Sutton, 1981:27)
  24. Quoted from Maclean, J., ‘Remarks on the Barony of Tailboys’ in Proceedings of the Society of Antiquaries of London, vol III, 1856
  25. L&P XVI 1489
  26. Elizabeth Blount received a gift in 1529 (Hayward, M., ‘Gift Giving in the Court of Henry VIII: The 1539 New Year’s Gift Roll in Context’ The Antiquaries Journal 85, 2005. Elizabeth’s gift is known from the reward given to her servant by the king on New Year’s Day 1529 for bringing her gift (L&P V 307)). In 1532 Elizabeth received the heaviest present of plate given to any lady below royal rank (The National Archives E101 420/15 f.3). Mary Boleyn also received a gift in 1532.
  27. L&P XVIII pt I 802(52)
  28. L&P XIX 312
  29. Lord Leonard Grey to Thomas Cromwell (The National Archives SP1/70, f.56)
  30. Lord Leonard Grey to Thomas Cromwell (The National Archives SP/70 f.144)
  31. The Life and Times of Sir Peter Carew p46
  32. Lisle Letters V 1513a
  33. L&P XIV 572

10 thoughts on “Margaret Skipwith of Ormsby: Mistress of Henry VIII by Elizabeth Norton”

  1. Esther says:

    Great post … thank you so much! Is it possible that Henry’s relationship with Mary Boleyn was early enough to fit into the same pattern as did Bessie Blount and Margaret Skipwith (i.e., her marriage to William Carey and the gifts to the couple were after the affair, not during it)?

    1. Claire says:

      Esther,
      That’s what I want to know! I know that historians date the start of the affair with Mary Boleyn to 1522 because of the jousting motto, but Mary was married at that time and it just doesn’t fit Henry VIII’s usual ‘MO’, does it? Isn’t it more likely that he had a fling with Mary before her marriage, perhaps when she first arrived back in England, and that the motto was aimed at another courtly love? Hmmm…

  2. Steve says:

    Fascinating – thank you. Interested that you refer to H VIII having a long lasting affair with Mary Boleyn when I understood that the evidence that they even had an affair was pretty thin?

  3. Ann Russell says:

    It occurs to me that Henry VIII is similar to another much married person, Elizabeth Taylor. She said that the reason she was married so many times was the she was uncomfortable having affairs, so she married the man, instead. At least Henry didn’t marry any of his wives twice.

  4. Anne Barnhill says:

    Great post–of course, I’m always interested to read more about the Sheltons! THanks!

    1. I am a descendent and would be very interested to hear of any informest
      Sorry, computer playing up!

  5. Moniek says:

    Interesting! I had never of her!

  6. BanditQueen says:

    Interesting post, not heard of this lady so nice to learn about her, but the letter of 3rd January does not prove she was Henry’s mistress and he was still in seclusion at this time after the death of Jane Seymour. I think the link to Henry is circumstantial and not evidence that she was his mistress, but intresting all the same.

  7. RiverCityGirl says:

    Interesting essay about my great-aunt, many generations removed. Thank you, Elizabeth, for a fascinating story!

  8. I am a descendent and would be most interested in any info re Shilton family. Have visited Little and Gt Snoring and the old chuch and beautiful hall now renovated by a German couple

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