(Updated, February 2024) A half-length portrait of an unknown Royalist naval commander. He wears a salmon-pink doublet, with braid on the front and sleeves. Over his left arm, a drape of blue material, perhaps a silk cloak, may also symbolize the sea. He holds the hilt of his sword in his right hand. In his left hand he holds a paper, thought to be either a chart or his naval commission. Behind the sitter, to the left, a contrived sculptural relief of an allegorical female figure holds a globe and dividers. To the right of the sitter, a ship is faintly painted to denote his identity as a naval commander.

Globes symbolized learning and scholarship, and with compasses or dividers, and other instruments, formed the attributes of geometry, one of the Seven Liberal Arts. In this sense it meant measurement of the earth. Since navigation is based on geometry and its derivative, trigonometry, the iconography of the portrait's background suggests geography and also navigation, appropriate for a naval officer.

While a number of names have been suggested, the identity of the sitter remains unknown. This small portrait may have been intended not only as a likeness but also as a demonstration of the sitter's loyalty to Charles I. It was probably painted when the king was at Oxford during the CIvil War and is one of Dobson's most glowingly coloured works. As in many of them there is a great deal included in a small area, with his Oxford work possibly because the canvases he could obtain were only of limited size, and spatial relationships can be unsatisfactory. There have been some visible adjustments in the figure here and it has been noted that the paper he is holding was added in after his left thumb was painted.

Although the artist's career was short, he succeeded van Dyck as court painter following the latter's death in 1641. He was with Charles I at Oxford in 1642 and between then and his early death, aged 35 in 1646, he painted many of the Royalists. His portraits include the royal children and also three known ones of the king. The contemporary commentator, John Aubrey, called him 'the most excellent painter that England has yet bred'. The present portrait (and one of the king) were both included in the 1983-84 Dobson loan exhibition at the National Portrait Gallery, which is the most recent major one. It was also in that at the Tate Gallery in 1951 (no.22) and its previous private owner, Sir George Leon (d.1947), lent it to one at the Burlington Fine Arts Club in 1938 (no.10). Leon had obtained it not long before after it was purchased on the English south coast by a London frame dealer, since its fine auricular frame also appears to be original.

The Museum purchased it via Spink's in January 1944, possibly from Arthur Tooth, the dealer with whom Leon seems to have placed it for sale in 1943. Fortunately it was at least not with Spink's when they were hit by a wartime air-raid on 25 February 1944, in which two other Caird Fund purchases (a portrait of Sir Walter Ralegh and a Battle of Solebay by van de Velde the Younger) were lost.

An extended discussion (2019-24) on the Art Detective pages of Art UK suggested the painting was possibly obtained from the family of Admiral Henry Killigrew (d. 1712) by the Duke of Chandos in or after 1727 and thereby probably wrongly identified as Thomas Killigrew (d.1682, the playwright) after it was bought as 'Mr Killigrew' by Sir Paul Methuen of Corsham House (now Court) at the Chandos collection sale of 1747. It was sold as Killigrew from Corsham in 1840 and equally wrongly suggested to be the Royalist soldier Sir Charles Lucas when resold at Christie's in 1842. It then passed rapidly via a dealer to the portraitist Frederick Richard Say (1804-68), since Henry Pierce Bone exhibited an enamel miniature copy of it (as Say's) at the Royal Academy in 1843. The Bone miniature is now in the Walters Art Museum, Baltimore, (WAM 38.99). The painting's pre-Chandos and post-Say provenance into the early 20th century is still uncertain.