[TRANSGENDER] Lot of 4 “Man-Woman” Items of Nicholai De Raylan and Others. Including a cabinet photo by Mrs. W.A. Reed (Quincy, IL); a photo postcard (RPPC) by Kite Studio (Chicago), annotated and dated 1906 on the face; a pitch booklet, “The Story of Nicholai DeRaylan;” and a 19th century quarter-plate daguerreotype of a “man-woman” or gender ambiguous subject, in a later wooden case. DeRaylan was born in Russia around 1873, the possible illegitimate child of a member of the nobility. In order to seek a share of her mother’s fortune, DeRaylan presented to authorities as a boy, hoping to better the chances of receiving an inheritance. Faced with a medical examination to determine her sex, De Raylan fled the country, eventually settling in Chicago around the 1893 World’s Fair. De Raylan lived and worked as a man in Chicago, even marrying two women, before dying from tuberculosis in 1906. It was only after De Raylan’s death when the story of his “secret,” “18 year masquerade” as a man became a sensationalized news story, reported across the country.