Group portrait of James Dempster Webster Gordon (1783-1850), with his wife Theodosia of Quinta do Monte, Madeira, and their sons, Webster and Russell, with their cousins Ameria and Geraldine Gordon at Balmaghie, Castle Douglas

James Dempster Webster Gordon (1783-1850) was the youngest son of Thomas Gordon (1737-1804) and his wife Agnes, daughter of John Dempster of Dunnichen, co. Forfar. His eldest brother Thomas William Gordon was a Captain in the Guards and died at Verdun in 1814. His elder brother James Murray Gordon (1782-1850), who was a Rear Admiral in the Royal Navy, succeeded to the family estate of Balmaghie, near Castle Douglas, Kircudbrightshire, which his father had acquired in 1786, and married Sarah Almeria, daughter of John Caulfield, Archdeacon of Kilmore. James Gordon became a merchant and lived on the island of Madeira, where he was a shareholder in the wine and general merchants Newton, Gordon and Cossart & Co., founded in 1745 by Francis Newton and William Gordon, who was presumably a cousin, who had fled Scotland following the failure of the Stuart cause. He married Theodosia, daughter of General Pollock of the East India Company service.

This group portrait apparently commemorates a visit that James Gordon and his family made to Balmaghie from Madeira. James Gordon is shown together with his wife, and their two young sons Webster Thomas Gordon and Russell Manners Gordon (1829-1906), and his elder brother's daughters Sarah and Geraldine. Both James Gordon's sons were educated at Eton. His younger son Russell, who lived in Madeira was to marry Philomena Gabriella, daughter and heir of Joao, 2nd Visconde de Torre Bella in the Portuguese peerage. On her father's death, Russell Gordon's wife suceeded to the family title and he was conferred the title of Conde de Torre Bella. On the basis of the apparent ages of the sitters this picture would seem likely to have been executed in the early-to-mid-1830s.