ON THIS DAY - 09 August 1586
- thedudleywomen
- Aug 9
- 3 min read
On This Day (09 August) in 1586, Mary Dudley, Lady Sidney, sister of Robert Dudley, 1st Earl of Leicester and Ambrose Dudley, 3rd Earl of Warwick, and former Gentlewoman of the Privy Chamber and close confidant of Queen Elizabeth I, died.

Mary had become widowed only three months earlier, on 05 May 1586, when her husband of 35 years, Sir Henry Sidney, Lord President of Wales, died at Ludlow Castle, located on the border of England and Wales, known as the 'Welsh Marches'. Despite years of service to Elizabeth I, Sidney had not been elevated to the peerage, as many of his contemporaries had been, as he was reportedly been unable to afford the costs that accompanied this position, despite the offer of a barony.

Mary had been in poor health since she had contracted smallpox whilst caring for the queen in October 1562, who herself was suffering and gravely ill from this virulent disease at Hampton Court Palace. Whilst Mary also recovered from the illness, it left her scarred and disfigured, with Henry himself commenting on her changed appearance. Mary subsequently withdrew from court and public life, although continued to attend events at the invitation of a grateful Elizabeth. Their relationship was soured, however, in 1578, with news of Mary's younger brother and the queen's longstanding 'favourite' Robert Dudley had secretly married Lettice Knollys, Countess of Essex, a perceived betrayal Elizabeth never forgave.
In her later years, Mary's health had deteriorated so much, that Henry began to speculate a future marriage; in correspondence sent to Sir Francis Walshingham, Secretary of State, in 1583, whilst celebrating the upcoming nuptials of their children (Sidney's eldest son Philip, to Walsingham's daughter Frances), Sidney expressed his opinions of his own marital status. Whilst he acknowledged that he himself was "toothless and trembling", being slightly older than his wife, he did not believe that his end was near, commenting that he was not “so old, nor my wife so healthy, but that she may die, and I marry again and get children” (Targoff, 2024, p.92).
However Mary defied expectations, outliving her husband, and dying in her early 50s, reportedly at her City of London home, Baynard's Castle, a magnificent Tudor mansion located on the banks of the Thames, near Blackfriars and St Paul's Cathedral.

Mary's funeral was reportedly held two days later, on 09 August 1586, at the Church of St John the Baptist, Penshurst, and was buried in the family vault beneath the Sidney Chapel, where other generations of the Sidney family were and would be interred. Her husband, Henry Sidney, had also been buried in the vault following a spectacular funeral procession and service, costing in excess of £700; however, Sidney's heart, at his request, had been placed in their daughter Ambrosia's tomb at St Lawrence's Church, Ludlow.
Mary's eldest son poet and scholar Sir Philip Sidney was in the Netherlands, along with his brothers Thomas and Robert, having accompanied their maternal uncle, Robert Dudley, 1st Earl of Leicester there. Leicester, who as appointed Governor-General of the Netherlands, was (unsuccessfully) attempting to provide leadership to allied-Dutch Rebels against the Catholic Spanish forces. Philip's own life would end only two months later, on 17 October 1586, weeks after being shot in the thigh during the Battle of Zutphen.



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