Sharp began painting this man, Laban Little Wolf, and his fabled uncle, Little Wolf, when he first moved to Montana in 1899. Contrary to Sharp's inscription, this is not the man who participated in the Custer Battle.  That was his very famous uncle of the same name.

Over the next half dozen years, Sharp got Laban to sit for him multiple times, including one pose similar to this in 1900. (related image, #150)

Sharp painted Laban at least twice in 1906, this version and another that shared a companion portrait of Laban's wife, Willow Woman.  (see #s 68 and 419)