Second son of Elizabeth Oakes Smith, Sidney Oaksmith was born in Portland, Maine in 1829. Following Appleton into business, he studied law after working in the US consulship in Haiti for some years and was admitted to the New York bar November of 1866. He drowned in a shipwreck off the coast of Florida in December 1869.

Image courtesy of Charles Pitts, reproduced as published in The News-Times (Beaufort, NC) Wednesday, January 19, 1994