This portrait relates to the picture, signed and dated 1661, which has appeared at auction twice in recent years (Sotheby's, London, 14 May 1986, lot 160; and Christie's, London, 10 November 1995, lot 71). At both sales that picture was catalogued as a portrait of Lady Churchill with her children Winston and Arabella Churchill, an identification that the present picture has also shared. When another version of this group portrait, from the collection of the Earls of Dartmouth, appeared at Phillips (10 July 2001, lot 121), the late Sir Oliver Millar identified the work as that listed in an inventory, of c.1735 (Staffordshire Record Office), as a half-length portrait of Mary Villiers with her son Esmé, 2nd Duke of Richmond, and her daughter Mary, the future Countess of Arran, by John Michael Wright.
The eldest child and only daughter of the celebrated George Villiers, Duke of Buckingham (1592-1628), Mary Villiers first married Charles Herbert, Lord Herbert of Shurland (1619-1636) on 8 January 1635 in the royal closet at Whitehall. After Herbert's death from smallpox whilst in Florence the following year, she married secondly the cousin of King Charles I, James Stuart, 1st Duke of Richmond (1612-1655) on 3 August 1637. They lived at Cobham Hall, Kent, but also remained prominent at court where the duchess's beauty was celebrated in verse and prose. Mary sat to Van Dyck for several portraits, including that, painted c.1637, in the Royal Collection, which shows her in the guise of Saint Agnes.
Their son Esmé died of smallpox in Paris in August 1660 and was buried on 4 September in Westminster Abbey. He is very much the central character in the present composition, in which he is shown in classical costume, tenderly encircled by his mother and sister. His recent death is alluded to by the presence of the torch with the dying flame and phial for capturing tears, the cut narcissus held by his sister, the Ouroborus - the metal circlet in the form of a snake consuming its tail - representing eternity, and the melancholic cypress trees seen in the evening landscape beyond.