The sitter of this unusual portrait is almost certainly Sir Robert Dudley, the illegitimate son of Robert Dudley, Earl of Leicester. Given his status as an illegitimate son, Dudley’s prospects at court were limited, and he was unable to inherit his father’s titles and political standing. He was, nevertheless, a cultivated and ambitious figure, and as can be observed clearly in the present work, he led an interesting life.

In a bold move, young Dudley, who lacked experience but wielded the same flair and confidence as his father, decided in 1594 to lead an expedition to the West Indies. Exploration was an opportunity to increase wealth, bolster status, and demonstrate bravery – an exciting prospect, no doubt, for a fledgling courtier eager to escape the shadow of his dominant father. After initial hesitation – likely on account of the ship’s value and Dudley’s inexperience – the Queen granted her permission and Dudley set sail on 6 November 1594 with a crew of 275. Although his initial attempt was scuppered by a storm, his second departure was successful, and by December, he was in Tenerife, where he captured two Spanish ships. The aim of the expedition was to pursue and capture Spanish vessels, so it was a positive start. Dudley and his men then sailed to Trinidad and anchored at Cedros Bay at the end of January 1595. It was there that he discovered an island which he named ‘Dudleiana’ and claimed it for the English crown. Following a failed attempt to find gold, Dudley and his fleet sailed north, where they captured a Spanish merchant vessel. Due to dwindling provisions, Dudley decided to sail home, and following a two-day tussle with a Spanish man-of-war, he finally arrived in St Ives, Cornwall, at the end of May 1595.

Following an expedition to Cadiz with Robert Devereux, 2nd Earl of Essex (cat.?), Dudley was knighted and soon after married Alice, daughter of Thomas Leigh of Stoneleigh. Following a failed attempt to claim his late father’s peerages and establish himself at court, he left England with his cousin Elizabeth Southwell and converted to Catholicism. The pair were married in Lyon, and later settled in Florence, where Dudley became a naval advisor to Ferdinand I, Grand Duke of Tuscany. In 1607, on refusing to travel back to England on the orders of James I, Dudley’s lands were confiscated, although he maintained contacts at the English court through a network of friends.

In his later years, Dudley self-published ‘Dell'Arcano del Mare’ (‘The Secret of the Sea’), a six-volume maritime encyclopaedia including an atlas of the entire world. It was published in 1646-7 and covers topics including shipbuilding, navigation, and astronomy. Dudley died in 1649, and his collection of scientific instruments is now on display in the Museo Galileo, Florence.

The present work is dated 1594 and was therefore commissioned to commemorate his first voyage and discovery of ‘Dudleiana’ – an event possibly recorded in the present work. It was likely painted sometime after his return to England in 1595 and before he left England for Italy in 1605. Dudley’s iconography is sparse, and his best-known portrait is Nicholas Hilliard's, in the National Museum of Fine Arts, Sweden, painted in the 1590s. Although painted in a different medium, Hilliard’s likeness of Dudley closely resembles the subject in our work.

In this portrait, Dudley is shown standing on the foreshore with his left hand on his hip and his right hand holding a halberd (a combination of spear and battle-axe). It is a pose of strength and defiance through which he adopts the guise of a conqueror. His intricately detailed helmet and shield are placed beneath a tree, symbolising strength, seriousness of purpose, and his willingness to fight for his cause. Ivy coils around the tree, a traditional symbol of immortality, perhaps here alluding to survival in the face of adversity. This sentiment is echoed in the small shield which hangs from a severed limb of the tree, bearing the Latin motto: 'non reiecienda reiecta' (‘that which has been rejected should not have been rejected').

The painting may be read as a statement of achievement, referring either to his claim upon land previously ignored or rejected by others, or to a more personal assertion in the face of his exclusion from his father’s inheritance. In either case, the portrait presents a deliberate act of celebratory self-fashioning. This sense of accomplishment is further reinforced by the small rocks flecked with gold in the lower left corner, positioned near the point at which he plants his halberd.

The present portrait was sold by George Sutherland-Leveson-Gower 5th Duke of Sutherland in 1924. According to an inscription on the reverse of the canvas, it was previously at Trentham Hall, Stoke-on-Trent. Trentham was inherited in 1605 by Sir Richard Leveson, who soon after married Katharine, the daughter of Dudley and his first wife, Alice. It was presumably through Katharine, therefore, that the present work found its way into the collection of the Dukes of Sutherland, who also owned a full-length portrait of Robert Dudley, Earl of Leicester, by Federico Zuccaro, which is thought to have been destroyed during the Second World War.