Chicago lawyer and civic leader.

Horace Oakley was born in Prescott, Wisconsin on June 2, 1861. He received a law degree from National University in Washington, D.C. in 1881 and then studied literature at the University of Michigan. He then returned to Chicago to practice law and was admitted to the bar in 1883. Soon afterwards he became associated with the firm of Ball and Oakley which eventually became Wood and Oakley. The two partners, Mr. Charles B. Wood and Mr. Oakley, retired in 1927. The firm specialized in county, state, and municipal bonds; it was said that banks and investment houses in Chicago would not underwrite or manage bonds unless their form and legality were sanctioned by Wood and Oakley. During all this time, Oakley maintained his interest in classical studies which began with his studies at the University of Michigan. He read and spoke French and Italian, and he traveled much in foreign countries.

Oakley’s financial acumen and personality—he seems to have been an engaging, graceful, and knowledgeable speaker and conversationalist—contributed to his ever increasing civic leadership. He became a trustee of the Newberry Library, the Art Institute of Chicago, the American School of Classical Studies at Athens, and the Orchestral Association. For the Library, the Institute, and the School, he made continual contributions of books, art, money, a building, and suggestions for increasing the collections on classical subjects. For the Orchestral Association, he took the lead in financial matters relating to the orchestra, its new building, and the players. In fact, he acted as the point man for negotiations with James Petrillo and the American Federation of Musicians (he provided for all these institutions in his will).

Consonant with his interests and scholarship in classical studies, Oakley developed other interests. He explored and researched the Franciscan Missions of California and wrote papers on the topic. He also lectured on the need for a league to enforce peace, which came to the attention of President Wilson’s advisor, Colonel Edward House, who placed Oakley on one of his peace committees. In 1918, Oakley resigned from this committee when he was invited, because of his legal skills and interests in international law, to join the American Red Cross Commission to Greece. Oakley was sent there as deputy commissioner, and given the rank of Major. He remained with this commission from September 1918 to April 1919, surveying and reporting on relief efforts in Macedonia. He and his fellow officers took snapshots of the people and places they encountered, and a number of these pictures appear in the photo album, “In Macedonia:”, which is included in this collection.

As a socially gregarious man—Oakley was a tall man of imposing size—Oakley seems to have been an oft-invited party and weekend guest as well as a member of social clubs such as the Wayfarers and literary or professional groups such as The Chicago Literary Club, the Law Club and, the Illinois Bar Association. He also owned a villa, La Badia, near Fiesole, in Italy, and frequently sailed to visit it. It is on one of his journeys there that Oakley’s overtaxed heart gave out; he died at sea in December, 1929 aboard a liner taking him to Naples. He was a lifelong bachelor.