A half-length portrait to left, with Digby in black and his right hand on his breast. The presence of a sunflower on the left is an allegorical symbol indicating his deep loyalty and constancy to the monarch, Charles I.

Digby - whose father was executed for involvement in the Gunpowder Plot of 1605 - was a courtier and author of books on philosophy and natural science; also a naval commander and diplomat. In 1623 he was in Madrid as one of Charles's household, when he was Prince of Wales. In 1625 he married Venetia Stanley. Noted for her beauty and intelligence, she was alleged to have been the mistress of Edward Sackville, 4th Earl of Dorset, while she was betrothed to Digby, who was abroad at the time. Digby detailed his romance to Venetia in his memoirs, 'Loose Fantasies'. Venetia was also the subject of several portraits by van Dyck but after nine years of marriage she died suddenly in 1633. van Dyck, a personal friend of her husband, painted the famous 'Lady Venetia Digby on her Deathbed' for him.

In 1627 Digby took a small privateer squadron to the Mediterranean in order to seize French ships in the Venetian port of Scanderoon or Alexandretta, in northern Syria. On 11 June 1628 he attacked the French and Venetian galleys he found there, winning a remarkable victory. As a Catholic, his intimacy with the king and queen roused the ire of the Long Parliament and on several occasions he was sent by the English Catholic Committee in Paris on diplomatic missions to Rome, including to ask for Papal assistance to Charles I during the Civil War. In 1644 he was appointed Chancellor to Queen Henrietta Maria in exile but, nonetheless, also became intimate with Cromwell ten years later, who employed him abroad on various diplomatic affairs. He finally returned to England at the Restoration.

Van Dyck painted several portraits of Digby and it is thought that this one is a studio copy of one of the versions. It is in a remarkable English auricular frame, contemporary with the painting, and a rare survivor in that it still shows its original silvering.