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Papers include biographical materials, photographs, diary, business correspondence, including a 1927 letter from Helen Keller, financial records, real estate materials, political materials, blueprints of his home, a photograph albums, and two scrapbooks.

Oakman’s financial records document land sales throughout metro-Detroit. His correspondence is mostly real estate related or regarding the Union Trust Company, although there are a few personal letters, mostly in the 1887-1921 and 1928-1944 folders. The correspondence is extremely acidic and fragile and should be handled with care. Of special note is a letter from Helen Keller (1880-1968) on behalf of the American Foundation for the Blind, Inc. (1927) and with the Dodge Bros., Inc. (1926). The correspondence was apparently kept in both alphabetical and chronological folders, resulting in this mixed arrangement.

The political materials document his Republican activities and interests. Of note here are the two letter press books which date from when he served as Pingree’s secretary when Pingree was campaigning to become Governor of Michigan. Most of this typed correspondence discusses how, where, and with whom to start Pingree Clubs in numerous Michigan towns.

The biographical information provides an interesting picture of Oakman’s career.

Two photograph albums show the Oakmans on vacation, at home, with friends, and their yacht. Among their friends were Francis, Dan, Horace, and John Dodge and Gar Wood. Two oversized scrapbooks, 1892-1944 and 1924-1946, include correspondence, greeting and holiday cards, programs, and newspaper clippings about the Oakmans.