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Although it is impossible to say if it was always part of the artist’s process to execute a preparatory sketch prior to painting each miniature, we do know that John Smart retained many hundreds of these sketches. A group of preparatory sketches—of which this portrait is one—descended through the Smirke family after Smart’s daughter Sarah gave a sketchbook containing preparatory portrait studies to her friend Mary Smirke, sister of the celebrated Victorian architect Sydney Smirke. This book was probably broken up around 1877 when it was divided between Sydney’s daughters Mary Jemmett and Mrs. Lange, whose portions were both sold at auction in 1928.<br>G. C. Williamson was the first to suggest that Smart’s sketches were well known and that they were preparatory studies for the painted miniatures. Williamson listed the names of sitters from the sketches known to him at the time, and they include Sir John Lester, the title formerly given to the sketch here. This designation was applied only to a paper backing that had been attached after the drawing had been removed from the sketchbook. There is no further evidence for this attribution, however. This sketch presents only the sitter’s head, with a slight suggestion of a high stock collar. <br>His head faces to the left, and his light hair is combed straight back with a flat curl above the right ear. He has gray eyes, and the background is unpainted. The work can be dated to around 1776 because of its size, which, when painted on ivory, would have been around 2 inches high. An inscription on the back of the drawing was discovered when the paper backing was removed in 1993. It is a fragment of a larger inscription, from which it has been cut. It is partly illegible but suggests that the work was intended to be set in a bracelet, and it gives some information about how the sitter was to appear in the finished miniature, including the description “scarlet coat . . . green waistcoat.” <br>This combination of colors might seem almost flashy, but it appears elsewhere in Smart’s work. These details seem to have been written in Smart’s hand, while the graphite inscription below—“Mr. De [?]”—was probably written later in another hand. Miniatures expert Arthur Jaffé remarked in 1948 that this portrait probably depicted John Lester of Poole, Dorset, who was knighted in 1802. However, this identity was based solely on the inscription on the later paper backing that Jaffé did not have the opportunity to see removed to reveal the inscription in Smart’s hand on the back of the drawing itself. There are no portraits of Sir John Lester known, and to this date, the finished ivory for which this preparatory sketch was presumably undertaken has not been discovered.