Sargent was one of the leading portraitists in the United States at the turn of the twentieth century. Born in Florence to expatriate parents, he spent his career shuttling between the major American and European capitals. He painted this penetrating portrait of the Boston banker, philanthropist, and Civil War veteran Henry Lee Higginson while visiting the United States to install his mural cycle at the Boston Public Library. In 1899, Higginson donated funds to build the Harvard Union (now the Barker Center), and the portrait was commissioned to hang in this new building. Cast in somber tones reminiscent of the Old Masters, the portrait emphasizes Higginson’s military service. The sitter’s Civil War cavalry cloak is spread across his lap, and a battle scar is visible on his right cheek.