Adolf Dehn's portrait of author Leo Stein, huddled close to the table with brow furrowed and fingers clenched, evokes the intensity of the physical act of creation. Brother of Gertrude Stein, Leo was also a distinguished writer and art critic. Like his sister, Stein spent much of his adult life abroad, particularly in Paris. While he supported the early modernism of Paul Cézanne and Henri Matisse, Stein broke with his sister over his distaste for cubism.
Dehn, a regular contributor of drawings to the avant-garde journal The Dial, knew Stein well. Here, he mimics Stein's strenuous activity with his own labor-intensive approach to drawing. Employing a rubbed-ink technique, Dehn made vigorous use of his fingers to soften lines and create shadows. The clever juxtaposition of technique and image is matched by the humorous omission of a chair for the seated figure.