Born in Rome, New York, James Milton Sessions (1882-1962) was a preeminent watercolorist and commercial illustrator best known for his depictions of maritime subject matter and modern wartime technologies. After attending the Art Institute of Chicago, he began working as a wheelsman aboard the Great Lakes ships from 1906 to 1914. Sessions continued his artistic practice and, during World War II, he worked as an illustrator for the Chicago Tribune where his career accelerated into acclaim.

While at the Chicago Tribune, Sessions worked closely with Colonel Robert McCormick, then publisher of the newspaper, to document the Pacific and European campaigns of World War II. His drawings and watercolors explored the chaotic imagery of combat, from jeep brigades cruising over muddy terrain to planes spiraling through the sky. Sessions was unafraid of depicting the polarizing narratives of war—both the imagery of success and the imagery of impending destruction. His military works were featured in a 1943 exhibition at the Metropolitan Museum of Art in New York and published in James Milton Sessions: American World War II Artist and Premier Brush Reporter. Today, Sessions is remembered as one of the greatest wartime illustrators of his time.

After the war, Sessions created illustrations and advertisements for the historically significant Vogue-Wright Studios. He produced calendars for Brown & Bigelow Co. in St. Paul, Minnesota and was featured in Field & Stream, Vintage Magazine and The Saturday Evening Post. A frequent traveler, Sessions loved to document his favorite places, which included the Great Lakes, the American Southwest, and Nova Scotia. His post-war works favor water and urban scenes, illustrating the interactions between daily life and the natural world.

Sessions received further attention towards the end of his life when, in 1962, the New York Graphic Society commissioned four works for their print catalog, American Masters Collection. Today, Sessions’ drawings and paintings are memorialized in major collections including the Art Institute of Chicago, the Cleveland Museum of Art, and the Metropolitan Museum of Art, New York.