The sitter (1863-1924) was married to Maud Emory Smith, later Le Baron (died September 12, 1949), and they had a son Emery Holland Smith (died January 28, 1927) who was married to Ann Hughes Smith (died August 9, 1946); their daughter was Ann Charlotte Emery Smith Waterous (1914-1986) who married baritone Allen Hugh Waterous (1904-1965) and had three sons, William, Herbert and Allen Jr.
He became President of the New York Central Lines on June 1st, 1919 after a long career in the service of the United States Railways which began as a messenger boy in Cleveland, Ohio, in 1879. He was killed when he fell from his horse in Central Park on March 8th 1924, and was buried in Kensico Cemetary.
The picture was described in the American Art News as having a background ‘…painted at Mr. Smith’s country home, Chappaqua, N.Y., and the picture is intended as an overmantel decoration for the living room there.’