This powerful and imposing portrait depicts one of the great tragic heroes of the Tudor age, Robert Devereux, 2nd Earl of Essex. Dubbed by his biographer Robert Lacy as An Elizabethan Icarus, whose dazzling career as favourite to Queen Elizabeth I was eventually dashed by treasonous rebellion resulting in execution, Essex's phenomenal rise and fall has captivated generations of those fascinated with the history of early modern England.¹ Painted during the 1590s, and possibly commissioned for a famous set of portraits for Weston Hall, Warwickshire, assembled by Ralph Sheldon (c. 1537–1613), this is the first time this painting has been sold in over one hundred and fifty years.

Born in 1565, the sitter was the son of Walter Devereux, 1st Earl of Essex (1541–1576) and his wife Lettice Knollys (1543–1634). His maternal great–grandmother, Mary Boleyn, was a sister of Anne Boleyn, second wife of King Henry-VIII and mother of Queen Elizabeth I, making him a first-cousin-twice-removed of the Queen, a connection which would stand him in good stead as a courtier. He first came to court in 1584 and fast became a favourite of the ageing Queen, replacing his step-father Robert Dudley, 1st Earl of Leicester (1532–1588), as Master of the Horse and being appointed to her Privy Council in 1593. In 1591 he was given command of a force sent to the assistance of King Henry IV of France and in 1596 distinguished himself in the Capture of Cadiz. This portrait must have been completed before this event, as his return from Cadiz was marked with him growing a beard, a feature captured in the well-known and often copied portrait by Marcus Gheeraerts (1561/62–1636) at Woburn Abbey, Bedfordshire.²

At the height of his powers, however, Essex overreached himself. Having talked himself into being appointed Lord Lieutenant of Ireland in 1599 he was dispatched to quell the rebellion led by Hugh O'Neill, Earl of Tyrone. Despite leading a force of 1,300 horsemen and 16,000 foot, however, Essex achieved little and his military failures, as well as perceived insubordination, led to growing calls for him to face trial on grounds of treason. Despite receiving the Queen's temporary mercy, he lost it all again early the next year when he became embroiled in plotting a coup d’état that was foiled by the Privy Council, who summoned Essex for questioning. Known for his hot headedness, he then tried to seize the City of London but the authorities held firm and he was forced to surrender at Essex House on the Strand when the building was surrounded by cannon. Essex was tried, found guilty, condemned to death and eventually beheaded at the Tower of London on 25 February 1601.

Essex's appearance in armour for this painting is significant. During the decade leading up to this painting his military career had advanced exponentially. This was particularly due to his socially-important appointment as colonel-general of the cavalry during the 1585–86 expedition to the Netherlands under the command of the Queen's favourite, Robert Dudley, 1st Earl of Leicester. His successes continued and the young Earl, now a Knight of the Garter, accompanied the Queen as General of the Horse during the famous military inspection at Tilbury, on the eve of the Spanish Armada in August 1588.

Aside from Essex's involvement in the theatre of war, the Earl was also a significant participant in the Tudor tournament and joust. The sumptuous gilded harness depicted in this portrait can be loosely identified as a tilting armour in the style produced by the Royal Workshops at Greenwich, with added embellishments and exaggerations where the gilded decoration is concerned.³ Essex's name appears in nearly all of the jousts and tournaments undertaken between 1586 and 1600.⁴ Part martial contest and allegorical performance art, these events were an arena in which Essex actively used his appearance to make political gestures. This included engaging writers such as Francis Bacon (1561–1626) to produce speeches and symbolic devices as part of the pageantry.⁵ It is very likely that his participation in tournaments resulted in the creation of portraits such as these. Both armoured portraits of the Earl at the National Gallery of Ireland, Dublin, also by Sir William Segar, and a miniature of the Earl by the miniaturist Nicholas Hilliard in the National Portrait Gallery, London (fig. 1), have been linked to his appearance in these martial spectacles.⁶

This portrait has long been attributed to Sir William Segar (act. 1580–1633), an elusive artist who was also actively employed as a painter of heraldry at court. It was connected by both David Piper and Roy Strong (see Literature) to another portrait of Essex believed to have been at Chavenage House, Gloucestershire, and now in the Museum of Fine Arts, Boston (fig. 2).⁷ The latter, in a poor state of preservation, uses the very same face pattern as the one found here. The presence of pouncing marks in the Jersey picture, visible with infra-red imaging, suggests that cartoons were employed to transfer the details onto the oak panel, a practice widely used by Elizabethan portrait painters of the period.⁸ In contrast to the militaristic connotations of this painting, the Boston portrait portrays Essex in the mode of a courtier, in his ornate black sashed robes and sporting a cartwheel ruff.

The Sheldon Portraits

This painting once formed part of the famous set of paintings at Weston Park, Warwickshire, the home of the local politician and tapestry maker Ralph Sheldon (c. 1537–1613). During the 1590s Sheldon had commissioned a significant set of portraits of at least twenty-two Kings and Queens, as well as English and European historical figures.⁹ Catherine Daunt has suggested that the group was formed by Sheldon, a Roman Catholic, to express and display visually his loyalty to the crown and in particular to Queen Elizabeth I herself.¹⁰ Most of the paintings, including this one, were dispersed at auction by a later owner of Weston in 1781 (see Provenance).¹¹

All conceived with the same arched-top format, the portraits were originally set into the architectural frieze of the Long Gallery at Weston Park. A later engraving of Weston by the antiquarian Henry Shaw (1800–1873), which has been shown to contain some fanciful inaccuracies, provides a sense of how exactly the set may once have appeared (fig. 3). The first record of the group was made by George Vertue (1684–1756) when he visited the house in 1737.¹² On his visit he noted portraits in ‘the great Room. all round almost. at the top. pictures of the Kings of England’. A list of some of the pictures he saw included:

‘h. K. Hen 5. H. 6. Ed. 4. R. 3. H. 7. his Qu. P. Arthur (P Arthur) with a white flower. H. 8. K. Franc, of franc Ed. 6. Qu. Scot. K. Hen of Franc. Card. Wolsey. Cromwell. Sr. T. More. & ... old Ld Cardigan.’¹³

Six other surviving identified panels from this set have often been given to an anonymous Tudor artist referred to as The Sheldon Master, examples of which are at Eton College, Berkshire; the National Portrait Gallery, London; Knebworth House, Hertfordshire; formerly at Audley House, Oxfordshire; and on the London art market.¹⁴ Daunt, who had only seen an old black and white image of the Essex portrait, suggested that all the paintings in the set were ultimately derived from pre-existing sources.¹⁵

However, comparison with other surviving panels speaks for the quality of the Jersey painting, thus warranting the attribution to Sir William Segar. A visual study of the few surviving Sheldon portraits suggests that several hands may have been employed in the set's creation, and that less able painters were employed in the historical portraits; including those of Cardinal Wolsey, Richard III, and Henry VI, for example. As the Sheldon set would have been compiled at the height of Essex's career, it seems likely that a significant painter like Segar would have been sought out to complete the likeness of one of the Queen's favourites. Dendrochronological analysis also supports this, as a study by Ian Tyers shows that the Baltic oak used for the panel support of this painting is not closely related to any other surviving panels analysed from the set.¹⁶ Analysis also indicates the much earlier and therefore unique dating of these boards, whose last tree rings predate any other surviving examples to have been studied.¹⁷ It is possible that Segar may have produced other portraits in the group or have been the artist in charge of the scheme. However, the survival of a mere seven out of twenty-two panels impedes further study and underlines the importance of this portrait.

In the mid-nineteenth century the painting was acquired by Lady Sarah Sophia Fane, Countess of Jersey (1785–1867), wife of the notable statesman George Villiers, 5th Earl of Jersey (1773-1859). Subsequently it hung at the Villiers family's principal seat, Middleton Park in Oxfordshire, where Sir George Scharf, the first director of the National Portrait Gallery, sketched it in his notebook during his visit there in May 1861 (fig. 4).

¹ R. Lacey, Robert Earl of Essex: an Elizabethan Icarus, London 1971.
² Oil on canvas, 213.4 x 127 cm. The Duke of Bedford, Woburn Abbey ; https://www.mediastorehouse.co.uk/fine-art-finder/artists/marcus-gheeraerts/robert-devereux-2nd-earl-essex-c-1596-12933849.html
³ We are grateful to Dr Tobias Capwell for pointing out that the basic form of this armour, including the shape of the pauldrons (shoulder pieces), does loosely conform to the Greenwich type. However, the etched decoration, which is particularly elaborate and lacking in rhythmic unity, does not follow any of the ornament found on surviving Elizabethan armours of this period and was probably taken from imagination of the artist.
⁴ A full list of Essex's participation in tournaments can be found in R. Strong, The cult of Elizabeth: Elizabethan portraiture and pageantry, London 1977, p. 206–11.
⁵ For references to Francis Bacon's draft speeches for the 1595 tilt at Whitehall, London, see Strong 1977, p. 209.
⁶ Oil on panel, 112 x 86 cm. NGI.283. The Dublin painting has often been associated with the Accession Day tilt of 1590, where the Earl is recorded to have dressed in black to honour the late Sir Philip Sidney (1554–1586); http://onlinecollection.nationalgallery.ie/objects/6929/portrait-of-robert-devereux-2nd-earl-of-essex-15661601 ; Watercolour and bodycolour on vellum, 24.8 x 20.3 cm. NPG 6241. Hilliard's miniature has been associated with the Earl's appearance at the Accession Day tilt of 1595. ; https://www.npg.org.uk/collections/search/portrait/mw09281/Robert-Devereux-2nd-Earl-of-Essex
⁷ Oil on panel, 113.3 x 86.4 cm. Accession Number 44.621; https://collections.mfa.org/objects/32907/robert-devereux-2nd-earl-of-essex-as-a-knight-of-the-garte;jsessionid=7527C5D8C33C9415AF5A65EC964E77C1
⁸ For a rare surviving example of an Elizabethan cartoon of Sir Henry Sidney on paper see Strong 1969, p. 289; https://www.npg.org.uk/collections/search/portrait/mw05806/Sir-Henry-Sidney?LinkID=mp04112&role=sit&rNo=0
⁹ C. Daunt, Portrait sets in Tudor and Jacobean England, unpublished dissertation, University of Sussex, 2015, vol. 1, pp. 134–41, vol. 2, pp. 223–35.
¹⁰ Daunt 2015, p. 140.
¹¹ A full list of these portraits, which were in the posthumous sale of William Sheldon (1715–1780) in 1781 (see Provenance) included, Henry IV, Henry V, Edward IV, Richard III, Henry VII, Queen Elizabeth, Charles V, Prince Arthur, Henry VIII, Francis King of France, Edward VI, Queen Mother of France, Henry of Bourbon, King of France, Cardinal Wolsey, L. Cromwell Earl of Essex, Sir Thomas Moore, Duke of Alva, Comte Eglemont, Duke of Guise, Duke of Parma and Earl of Essex (this painting).
¹² 'Vertue's Note Book', in Walpole Society, vol. 24, 1935–1936, p. 140. Although a portrait of Essex cannot be found in this particular list, probably because it was not as noteworthy as Royal sitters, it is undeniable that the portrait follows the same format as the others. The portrait of Essex was also not mentioned in Horace Walpole's visit to Weston in September 1768, which too focused on the royal portraits, see P. Toynbee, 'Horace Walpole's journals of visits to country seats', in Walpole Society, vol. 16, 1927–1928, p. 62.
¹³ Walpole Society, 1935–36, p. 140.
¹⁴ Edward IV, oil on panel, 85.1 x 54.6 cm. Sold in these rooms, 5 July 2012, lot 195 ; https://www.sothebys.com/en/auctions/ecatalogue/2012/old-master-british-paintings-day-sale-l12034/lot.195.html ; Richard III, oil on panel, 83.2 x 56 cm. With Philip Mould & Co, London ; http://www.historicalportraits.com/Gallery.asp?Page=Item&ItemID=1030&Desc=King-Richard-III-%7C-The-Sheldon-Master ; Thomas Wolsey, oil on panel, 83.8 x 55.9 cm. The National Portrait Gallery, London. NPG 32.
; https://www.npg.org.uk/collections/search/portrait/mw06903/Thomas-Wolsey ; Henry VII, oil on panel, 85 x 57 cm. Eton College. ; https://catalogue.etoncollege.com/object-fda-p-451-2013 ; Henry VI, oil on panel, 85 x 75 cm. Eton College. ; https://catalogue.etoncollege.com/object-fda-p-122-2010 ; The Knebworth paintings, both oil on panel and measuring 83.8 x 58.4 cm. and 84.5 x 57.3 cm. respectively, are reproduced Daunt 2015, vol. 2, p. 224.
¹⁵ Daunt 2015, pp. 136–37.
¹⁶ Ian Tyers, Dendrochronological Consultancy Report 1468. May 2023. Tyers has undertaken analysis on the aforementioned portraits of Richard III, Henry VI, Henry VII and Cardinal Wolsey.
¹⁷ The results indicates that these were eastern Baltic boards derived from 2 different trees, with a latest heartwood ring of 1544. Allowing for the likely amounts of missing sapwood this panel dates from after c. 1550. The the last tree rings found in the paintings referenced in n. 16 date to 1572, 1570, 1570 and 1559 respectively.