My Buddy Montoyo is a quirky and endearing portrait of H. C. Westermann’s friend and fellow ex-Marine, Luis Ortiz. Like Westermann, Ortiz shared an interest in acrobatics and art, and the two became friends during their deployment in World War II. In addition to this painting, Ortiz is also the subject of a later, sculptural portrait by Westermann.

After joining the Marine Corp at the age of 20, in 1942, Westermann served for three years as an anti-aircraft gunner on the U.S.S. Enterprise, seeing intense combat and enduring numerous Japanese kamikaze attacks while in the Pacific theatre. After the war, deferred for a year from entering the Art School at the Art Institute of Chicago, Westermann formed a two-man balancing act with Wayne Uttley, calling themselves “Wayne and Westermann.” Together, they performed in the U.S.O.’s post-war tour of Japan and China. Westermann returned to Chicago in the fall of 1947 and entered the Art Institute of Chicago, where he became a part of the small but slowly growing art scene. While drawing and painting occupied Westermann’s interested in the early fifties, his interest gradually drifted toward sculpture, and by 1954, he stopped painting completely for a period of years. This painting, My Buddy Montoyo, falls in the end of the artist’s early painting career and exhibits “the kind of expressive freedom that prevented specific classifications of his work [and] inspired succeeding generations of artists. His influence was particularly prevalent among third generation Chicago painters such as Ed Nutt, Ed Paschke and Karl Wirsum.” (Barbara Haskell, H. C. Westermann, exh. cat., Whitney Museum of American Art, New York, 1978, p. 25.)