This monochromatic watercolor depicts the noted Seneca chief and orator Red Jacket (original name Otetiani, also called Sagoyewatha, c. 1750–1830), as a mature individual, seated on a rocky outcropping beneath a tree. He cradles a long-stemmed pipe in the elbow of his left arm; a tomahawk rests on the ground to his left. He wears a striped tunic with fringes at the edges of its cape and at its hem, leggings, and moccasins. Hanging from a ribbon at his neck is a large “peace medallion” depicting two figures.

Eastman created this portrait of Red Jacket basing his image primarily on a painting by Charles Bird King, a lithographed version of which Eastman sent to his engraver for reference. King’s portrait (one of three) had been commissioned by Thomas L. McKenney, Superintendent of Indian Affairs, and was probably painted in 1827. A version of this portrait accompanied Red Jacket’s biography in McKenney and Hall’s History of the Indian Tribes of North America. Eastman’s full-length version required depiction of a complete costume, and it is clear that he took liberties, combining elements from disparate native groups. The present portrait by Eastman appeared in Henry Rowe Schoolcraft’s extensive study Historical and Statistical Information Respecting the History, Condition, and Prospects of the Indian Tribes of the United States. Commissioned by an act of the United States Congress in 1847, it was published under the direction of the Bureau of Indian Affairs in six volumes from 1851 to 1857.