Kilderbee was an Ipswich attorney who became a close friend of Gainsborough. The two men exchanged letters that are now lost, but which were described in the 19th century as ‘brilliantly eccentric and too licentious to be published’. A close examination reveals (and an X-ray confirms) that the portrait has been repainted in everything except the face. This perhaps occurred around 1783, as it was in that year that Kilderbee accompanied Gainsborough on a tour of the Lake District.