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Duncan Phillips noted Milton Avery's artistic promise early in the painter's career, purchasing his first work by him in 1929; however, it was not until 1942 that he judged Avery to have reached his full potential. Phillips admired his art for its striking compositions, emphatic shapes, and sensitive, lyrical colors similar to those of Matisse and Picasso. Most of all, he appreciated Avery as an independent painter who retained his individuality in subject and technique and who stood at the threshold of a new American art.
Although Phillips never met Avery, he was aware of him as early as 1928, when Avery had his first one-person show in New York. It is not known whether Phillips visited this exhibition; however, he made note in an art magazine about seeing an Avery still life inspired by Matisse and Braque. Phillips appreciated Avery’s talent and thought he would become a major painter, and he soon acquired his first Avery, Winter Riders, 1929, for the museum. Painted in a subdued palette dominated by browns, Winter Riders represents the artist's early style of muted color, expressive brushstrokes and flattened forms. Although Phillips expressed some reservations about Avery's somewhat somber palette, he admired his flair for daring composition.
Phillips's interest in Avery resurfaced in 1942 when he bought Harbor at Night, 1932, an aerial view of Gorton's Fishery in Gloucester, Massachusetts, painted in harmonious tones of blue and green. In Avery’s works of the 1930s and early 1940s, his flattened shapes had become brighter in color and more varied in texture—matte areas detailed with gestural brushstrokes and incised lines. Believing that Avery showed a great deal of promise, Phillips gave him his first one-person museum exhibition in 1943, displaying works spanning the previous decade and surveying his full range of subjects—including the artist's favorite, his daughter, March, whom he depicted frequently. Girl Writing, 1941, one of the works in the 1943 exhibition, and the drawing for Girl Writing, 1941, represent nine-year-old March busily working at a table in the family's New York apartment.
Although Avery was gaining favorable recognition in New York art circles at the time, Washington critics barely took note of the 1943 exhibition. Despite this, Phillips remained supportive—"I do not want to lose this opportunity of giving recognition and encouragement to Avery and adding to his representation in the collection"—and purchased five works from the 1943 show. His continuing interest in this period is demonstrated by his purchase in 1956 of the oil Trees, 1936.
Phillips continued to admire Avery even as his style became increasingly abstract during the 1950s, earning him high praise from most critics. By 1965, Phillips had acquired three late works, the subdued 1954 gouache, Morning Landscape, the vividly colored March on the Balcony, 1952, and the boldly simplified Black Sea, 1959, thereby rounding out the unit as a survey of the high points of Avery's career.
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