The sitter was the son-in-law of Adelaide Sartoris (née Kemble), the former opera-singer and hostess who met Leighton in Rome in 1853 and has been described as 'the most important woman in his life.' Her daughter Mary Theodosia ('May'), born in 1845, married Gordon in 1871. The portrait was painted a year after Leighton's likeness of the explorer Richard Burton (National Portrait Gallery), generally regarded as his masterpiece in portraiture, and is similar in format and pose. It was exhibited at the inaugural exhibition at the Grosvenor Gallery in 1877, and was described by the Times in its review as 'fine and characteristic'.

Leighton also painted two portraits of May Sartoris: a dramatic full-length, c.1860 (Kimbell Art Museum, Fort Worth, Texas) and a more conventional seated likeness, 1875 (Leighton House).