[1] During the American Civil War, Oaksmith was charged with outfitting a ship for slave trading and was convicted, imprisoned, and escaped.
During the period when he was a fugitive from the law, he engaged in blockade-running for the Confederacy, but after his pardon he served as a North Carolina legislator, where he supported the rights of ex-slaves.
[2]: 60 Walker made Oaksmith Minister Plenipotentiary to the United States,[2]: 60 and Oaksmith arranged for the supply of Walker's small military force and convinced James Neal, son of writer John Neal, to travel to Nicaragua in 1856 to join the effort.
[2]: 231 In 1874, he won election as an independent candidate to the state house of representatives, where "he was ardently anti-Klan and in favor of protecting the rights of ex-slaves".
With his second wife, Augusta Mason, Appleton had eight children: Bessie, Corrine, Mildred, and Pauline all drowned on July 4, 1879 when the family's boat capsized.