This portrait of Indian fighter Colonel (later Brigadier General) David Perry, is a pivotal picture in Henri's career as well as in the formation of "The Eight." According to Bennard Perlman in Robert Henri, Painter, the artist, a member of the jury and an Academician of the National Academy of Design, submitted three paintings to the Spring Annual. However, when only this portrait was unanimously accepted by the jury who also rejected works by Glackens, Luks, Shinn, Kent and Sprinchorn, Henri removed his other two pictures from consideration. This action led to his establishment of a more radical group of artists who influenced American art from 1907 onward, known as "The Eight." This portrait, however, remained in the Academy show and is recorded in the artist's notebook E as no. 74: "New York, Feb. 7, 1907, 39 1/2 x 81, property of Miss Clara G. Perry."

A bust portrait of this subject was sold in these Rooms on October 24, 1979, lot 220.