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The son of department store salesman Thomas W. Dale and his wife Jane (née Roberts), Chester Dale attended the Peekskill Military Academy, but left before graduation to begin a Wall Street career. He started as an office boy, and later became a runner for F.J. Lisman, a firm specializing in railroad securities and other corporate bonds. By 1904 Dale was trading on his own at the firm of Pollock and Vaughan and in 1909 started a business with his friend William C. Langley, concentrating on railroad mortgages and utilities. On April 28, 1911, Dale married Maud Murray (1876-1953). Seven years later he became a member of the New York Stock Exchange, consolidating power companies and selling their stocks and bonds to the public, and was able to retire a wealthy man in 1935.
The Dales led a very active social life which was often reported in the New York papers. At Maud's suggestion the couple began collecting American paintings; among their favorite artists was their neighbor, George Bellows. They began to collect European paintings, especially French, on regular trips to Europe after World War I. Chester Dale became a partner in Paris' Galerie Georges Petit in the early 1930s, while Maud selected most of works they purchased. Mr. Dale often commented that he had the inquisitiveness and Maud had the knowledge. Maud Dale died in 1953. On 27 May of the following year, the seventy-one year old Dale married his late wife's long-time secretary, Mary Towar Bullard.
Dale served on several museums' boards of trustees, starting with The Museum of Modern Art in 1929, the year it opened, and remaining in the post until 1931. In 1943 he became a trustee for three other museums: Art Institute of Chicago (until 1952), the Philadelphia Museum of Art (until 1956), and the National Gallery of Art. Dale served as President of the Board of Trustees at the National Gallery from 1955 until his death in 1962. Large segments of his collection were lent to both the Chicago and the Philadelphia institutions in the 1940s, but in 1951 Dale lent the works instead to the National Gallery. After his death in New York City, it was revealed that the bulk of the Dale collection would stay in Washington as Dale's bequest. While somewhat uneven in quality, the highly personal Chester Dale Collection contains many exceptional works by old masters including Tintoretto, El Greco, and Rubens, as well as by impressionists, post-impressionists, and "School of Paris" artists. Among the better American paintings in the collection are those by Bellows, Mary Cassatt, Benjamin West, and Guy Pène du Bois.