This portrait has only recently been reidentified at Sir Rowland Winn 5th Bt. (1739-1811), who engaged Robert Adam to continue the work on Nostel Priory in Yorkshire (now National Trust) begun by the 4th Baronet. Having inherited Nostell in 1765, Rowland and his wife, Swiss heiress Sabine d'Hervart picked up the project with vigour, employing not only the most fashionable architect Robert Adam, but leading craftsmen such as Thomas Chippendale and Joseph Rose. Designs were updated and expanded, particularly after the birth of a son and heir in 1775. Lack of money again slowed progress and work came to an end with the 5th baronet’s death in a carriage accident in 1785.

Here, in an extraordinarily detailed miniature from 1767, Smart portrays Winn in what must have been an important commission during his fledgling career. Smart had just become a father for the second time to Anna Maria (1766–1813), later Mrs Robert Woolf. His son, also called John, is likely to have died young in 1762. John was possibly born out of wedlock, as Smart only married the child’s mother, Mary Anne (Marion) Howard, in June 1763, at St Stephen, Coleman Street. According to the artist Thomas Jones, Smart had met her in a Covent Garden brothel (or ‘banio’) and it appears that their marriage did not last long. Mary Anne eloped to Rome not long after with the artist William Pars, leaving Smart with the upbringing of their children.

Winn would have been an unusual patron for Smart, whose clientele were generally drawn from the emerging merchant classes (who had wealth, but not aristocratic lineage). It would be these patrons who he followed to India in 1785 and stayed for ten years. At this point (from 1765) Smart was working from a studio in Berners Street, Soho, but he would likely have painted Sir Roland at his London house in St. James’s Square in Mayfair.