Portrait of Robert Devereux, 2nd Earl of Essex (1565-1601), three-quarter-length, in a black doublet with white ruff and cuffs, wearing a badge of the Order of the Garter, the 'Lesser George'

Amongst the various depictions of Robert Devereux by the portraitists active at the Tudor court, there is an intriguing affinity between the head and shoulders in the present portrait and a miniature on vellum by Isaac Oliver at the National Portrait Gallery, London (inv. no. 4966).

Robert Devereux was the elder son and heir of Walter Devereux, 1st Earl of Essex (1539-1576), and his wife Lettice née Knollys (1543-1634). After his father’s death in 1576, Essex became a ward of the crown and was the responsibility of William Cecil, Lord Burghley, Lord Treasurer. After studying at Trinity College, Cambridge, he joined his stepfather, the Earl of Leicester, at court in 1585, and subsequently accompanied him to war in the Netherlands, returning in 1586 as a war hero. He quickly became a favourite of Queen Elizabeth I and was made Master of the Horse. In 1589, he took part in Sir Francis Drake’s English Armada, after the Queen specifically forbade him from going. He returned after the failure of the English fleet to take Lisbon. In 1590, he secretly married Frances (1567-1632), the widow of Sir Philip Sidney, but the marriage was revealed when it became clear that the Countess was pregnant, in 1591. Shortly afterwards she gave birth to Robert Devereux, Lord Hereford (later 3rd Earl of Essex). They had two more sons and four daughters together, despite Essex’s dalliances with other women at court. Enjoying a high public profile, Essex received as many dedications as the Queen during the 1590s and was a key patron of portraiture, poetry and music, as well as being a poet himself.

During the late 1590s, Essex campaigned to be promoted as the Queen’s next Chief Minister, after Lord Burghley’s retirement, and achieved a small victory at Cadiz. A failed expedition to Spain weakened Essex’s influence at Court, although he retained the Queen’s favour and was created Earl Marshal in 1598. That same year, however, after an argument with the Queen over the choice of a new Lord Deputy of Ireland, Essex removed himself from court. In 1599, as the new Lord Lieutenant of Ireland, he sailed to Ireland to command the Queen’s forces against the Earl of Tyrone (as part of the Nine Years’ War, 1594-1603), but contrary to the Queen’s orders, conferred a large number of knighthoods on his soldiers, wasted funds, garrisoned his men, all of which resulted in several defeats. Sensing that victory was no longer in his grasp, Essex reached a truce with Tyrone, independent of orders from the Crown. Although Essex was ordered not to return to court, he did, and was subsequently imprisoned. On 5 June 1600, he was charged with acts of insubordination whilst in Ireland and detained under house arrest, but granted his liberty on 26 August.

When his monopoly on sweet wine customs was not renewed, Essex led a failed coup in 1601. Arrested and tried for treason, he was executed at the Tower of London on 25 February 1601—the last person to be beheaded there. Despite his downfall, Essex’s legacy endured, with historians praising his military leadership, intelligence efforts, and cultural patronage.