Sholto Johnstone Douglas of the writer Oscar Wilde. When Wilde sued Bosie's father for libel when accused of "posing as a somdomite" ("sic"), this led to Wilde's downfall and imprisonment. In 1895, when during his trial Wilde was released on bail, Sholto Johnstone Douglas stood surety for £500 of the bail money. In his "Noel Coward: A Biography" (1996), Philip Hoare writes of "...late nineteenth-century enthusiasts of boy-love; writers, artists and Catholic converts inclined to intellectual paedophilia, among them Wilde, Frederick Rolfe, Sholto Douglas and Lord Alfred Douglas." As a portrait painter, Douglas belonged to the period of John Singer Sargent and "...led
Lord Alfred Douglas did give him occasional handouts. When Wilde died in 1900, he was still bankrupt. Douglas served as chief mourner, although there reportedly was an altercation at the grave between him and Robbie Ross. This struggle developed into a feud which would preview the later litigations between the two former lovers of Wilde. After Wilde's death, Douglas established a close friendship with Olive Custance, an heiress, poet and bisexual. They married on 4 March 1902. Olive Custance was in a relationship with the writer Natalie Barney when she and Douglas first met. Barney and Douglas eventually became close friends and Barney