Oscar S. Gifford, first superintendent at the Canton Asylum for Insane Indians, was the exception to the rule–he did not live on the asylum grounds as most asylum superintendents did. He already had a home in Canton, and his assistant, Dr. John F. Turner, had a family who needed the rooms set aside for the superintendent. Gifford had a room at the asylum where he could spend the night if needed, and boarded a horse there, as well.
Gifford married Phoebe Fuller in 1874 and had a son named Oscar Bailey, who grew up in Canton and eventually became a pharmacist in Minnesota. Bailey and his wife lived in Minneapolis, but visited Canton frequently and were able to enjoy the hospitality offered within a large, comfortable home.
Gifford had been a widower several years before he married Jenny H. Rudolph in 1899; they had a daughter named Frederica. The Giffords entertained frequently, were involved in community affairs, and belonged to many clubs. Jenny Gifford was instrumental in bringing a fine library to Canton through a donation from the wealthy philanthropist Andrew Carnegie.