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Douglas Sheffield, Baroness Sheffield
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Douglas (or Douglass) Sheffield, Baroness Sheffield, née Howard, (1545 – 1608) was the mother of Robert Dudley, styled Earl of Warwick, the illegitimate son of Robert Dudley, 1st Earl of Leicester, Queen Elizabeth I's favorite. Seventeen years after the earl's death, she claimed in court that she had been his secret wife, notwithstanding she had herself remarried while the earl was still alive.
Douglas Howard was the daughter of William Howard, 1st Baron Howard of Effingham, and Margaret Gamage. Her father was brother of Elizabeth Boleyn, Countess of Wiltshire, uncle to Anne Boleyn and great-uncle to Elizabeth I. Douglas was thus herself a first cousin to Anne Boleyn. One of her brothers was Lord High Admiral Howard of Effingham.
Douglas Howard was at Court in c.1559, probably as a maid of honour. She married a wealthy peer, John Sheffield, 2nd Baron Sheffield, around 1562. They had two children, Elizabeth Sheffield, who married Thomas Butler, 3rd Earl of Ormonde and died in November 1600. The son was Edmund Sheffield, 1st Earl of Mulgrave (7 December 1565 – 6 October 1646).
Lady Douglas Sheffield began an affair with the Earl of Leicester, either before or shortly after the death of John Lord Sheffield, which occurred in December 1568.
Sometime in the following years, Leicester wrote Douglas a remarkable letter, pondering on the history of their love, and explaining to her the reasons why he could not marry, not even to beget a legitimate heir; it would result in his "utter overthrow":
You must think it is some marvellous cause, and toucheth my present state very near, that forceth me thus to be cause almost of the ruin of mine own house...and yet such occasions is there...as if I should marry I am sure never to have [the queen's] favour.
He continues, proposing to accept one of the suitors for her hand, who she had so far declined for his sake: "The choice falls not oft, and yet I know you may have now of the best; and it is not my part to bid you take them...so it were not mine honesty to bid you refuse them." However, he says, he still loves her as he did in the beginning. Yet he would help her, in case she wanted to marry elsewhere for reasons of respectability: "for when you have made your election you shall find me a most willing and ready friend to perform all good offices toward you". In May 1573, it was observed by the court correspondent, Gilbert Talbot, that the Earl of Leicester was pursued by Lady Douglas and her sister:
There are two sisters now in the court that are very far in love with him, as they have long been; my Lady Sheffield and Frances Howard. They (of like striving who shall love him better) are at great wars together and the queen thinketh not well of them, and not the better of him.
In August 1574, Douglas' son Robert was born. Leicester acknowledged paternity of his "base son", and took custody of him, being very fond of him and caring much for his well-being and education.
Around 1578, in order to marry his new lover, Lettice Knollys, widow of Walter Devereux, 1st Earl of Essex, Leicester wanted to end his relationship with Douglas Sheffield. They had a meeting at Greenwich in the garden, where he wanted her to agree to end the affair, offering her 700 pounds a year. According to her own later words, she passionately rejected the offer. Leicester also became furious, saying he could as well part from her, leaving her penniless. Upon some reflection, she accepted the offer at last. Leicester, newly married, kept a portrait of Lady Douglas Sheffield in his country house at Wanstead until his death.
Second marriage and Star Chamber trial
On 29 November 1579, Douglas married Sir Edward Stafford, whose mother, Dorothy Stafford, Lady Stafford served as Mistress of the Robes to the queen, and was very influential with her. Edward Stafford was appointed English ambassador to the court of Henry III of France, and Douglas accompanied him. They resided in Paris from 1583 till 1591, Douglas moving in the highest circles of society as the ambassador's wife. They had two sons, who are thought to have died young. Edward Stafford honoured his wife greatly, he had to cope with the fact though, that Douglas was still emotionally agitated by remembrances of the Earl of Leicester. Stafford himself was politically opposed to Leicester, and the personal component only aggravated this.
After the death of Elizabeth I, in May 1603, Douglas' son, Sir Robert Dudley, began trying to establish his claim to the title of Earl of Leicester. He had been apparently told by a shadowy adventurer called Thomas Drury that his parents had been secretly married . The case ended up in the Star Chamber (1605) and aroused great public interest. The court heard ninety witnesses for Dudley and fifty-seven for Leicester's widow, the Countess of Leicester and former Lady Lettice Knollys. Lady Sheffield declared in writing (she did not attend the trial personally) that Leicester had solemnly contracted to marry her in Cannon Row, Westminster in 1571, and that they were married at Esher, Surrey, "in wintertime" in 1573. Yet all of the ten putative witnesses ("besides others") to the ceremony were long dead since. Neither could it be remembered, who the "minister" was, nor the exact date of the marriage. As an explanation for marrying Edward Stafford, she asserted that Leicester had tried to poison her, and, "life being sweet", she determined to marry "for safeguard of her life". The Star Chamber rejected the evidence and fined several of the witnesses. It was concluded that Sir Robert Dudley had been duped by Thomas Drury, who in his turn had sought "his own private gains".
Sir Edward Stafford died while the proceedings were in progress. He had to answer questions regarding his wife's putative marriage with the Earl of Leicester. In his answers he wrote that he had asked Douglas back in December 1579, on the Queen's command, if she had been contracted to Leicester, to which "she answered with great vows, grief and passion that she had trusted the said earl too much to have anything to show to constrain him to marry her."
Douglas herself died in 1608. In her will she left a black velvet bed among other things to her "honorable and beloved son Sir Robert Dudley". She was buried on 11 December 1608.
^ Warner p. ii
^ Rickman p. 49
^ Read p. 21
^ Rickman p. 51
^ Read pp. 15–16; Jenkins p. 186
^ Read p. 25
^ Read pp. 25, 24
^ Read pp. 23–24
^ Read p. 23
^ Read p. 26
^ Wilson p. 207
^ Warner p. vi
^ Warner p. vi; Wilson p. 246
^ Jenkins p. 217
^ Jenkins p. 283
^ Jenkins p. 249
^ a b Doran p. 161
^ Jenkins p. 298
^ Jenkins pp. 285–286, 325; Haynes p. 44
^ a b Warner p. xli
^ a b Warner p. xlv
^ Warner p.xlvi; In the 19th century, the question of Sir Robert Dudley's legitimacy was again raised in the House of Lords, but again, it remained unresolved. Historians have had different views on the problem: Wilson p. 326 believes in a marriage; Warner p. v–ix, xxxviii–xlvii is very sceptical; Read p. 23, Adams pp. 144–145, and Rickman p. 51, reject it.
^ Warner p. xlvi
Adams, Simon: Leicester and the Court: Essays in Elizabethan Politics Manchester UP 2002 ISBN 0719053250
Doran, Susan: Monarchy and Matrimony: The Courtships of Elizabeth I Routledge 1996 ISBN 0415119693
Haynes, Alan: Invisible Power: The Elizabethan Secret Services 1570–1603 Alan Sutton 1992 ISBN 0750900377
Jenkins, Elizabeth: Elizabeth and Leicester The Phoenix Press 2002 ISBN 1842125605
Read, Conyers: A Letter from Robert, Earl of Leicester, to a Lady The Huntington Library Bulletin No.9 April 1936
Rickman, Johanna: Love, Lust, and License in Early Modern England: Illicit Sex and the Nobility Ashgate Publishing 2008 ISBN 0754661350
Warner, G.F: The Voyage of Robert Dudley to the West Indies, 1594–1595 Hakluyt Society 1899 
Wilson, Derek: Sweet Robin: A Biography of Robert Dudley Earl of Leicester 1533–1588 Hamish Hamilton 1981 ISBN 0241101492
Douglas Sheffield's Timeline
Lambeth, Surrey, England
December 7, 1565
Boston, Lincolnshire, England
August 7, 1574
December 11, 1608
Effingham, Surrey, England
December 11, 1608
Effingham, Surrey, England