Horace Sweeney Oakley, Chicago lawyer, recognized authority on municipal bonds, classical scholar, and patron of the arts, was born in Prescott, Wisconsin, on June 2, 1861 to George McCready and Susan Jane (Sweeney) Oakley. When he was two, the family moved to Chicago where Horace attended public schools. Following graduation from Chicago High School in 1879, he studied law at National University Law School in Washington, D.C. until 1881. From 1881 to 1883, Oakley studied literature at the University of Michigan, where he was an active member of the Psi Upsilon fraternity.
After a “Grand Tour” of Europe, Oakley returned to Chicago to practice law, having been admitted to the Bar of Illinois on November 16, 1883. He obtained desk space in the office of John A.J. Kendig and remained there until 1888 when he established a partnership with Farlan Q. Ball. The firm of Ball and Oakley continued until 1892 when Charles Wood entered the firm and it was henceforth known as Ball, Wood, and Oakley. Ball was elected judge of the Superior Court of Illinois in 1895 but Wood and Oakley remained partners. Gradually, their attention turned entirely to the examination of conditions upon which state, county, and municipal bonds were issued, and to rendering opinions on their legality. They became the foremost authorities in the Midwest on municipal bonds, establishing, in effect, a legal monopoly. No Chicago bank or investment group would underwrite or handle municipal bonds unless approved by the firm. In 1927, both Wood and Oakley retired and dissolved the firm.
During the First World War, Oakley served as deputy commissioner of the American Red Cross in charge of relief and reconstruction in Macedonia. For this work, he received several orders of merit from the Greek and Italian governments including decoration as “Knight Chevalier, Order of the Redeemer of Greece” in 1919. Also, for Col. Edward House, President Woodrow Wilson's private diplomatic adviser, Oakley prepared a collection of data and interpretation on international law regarding the freedom of the seas to be used by the American peace delegation at Versailles.
Oakley's avocational interests reflect his Renaissance character. He was a classical scholar, particularly dedicated to archaeology, a patron of the arts, and an enthusiastic traveller of Italy, Greece, and Turkey. He spent his retirement winters in the hills above Florence in his beloved Villa La Badia.
Oakley was a trustee of the American School of Classical Studies in Athens, Greece, and financed the construction of a house at Old Corinth for the use of the faculty and students. He was also a member of the Visiting Committee of the Department of Art and Archaeology of Princeton University. Oakley identified with many of Chicago's outstanding cultural and educational endeavors. He became a member of the board of trustees of the Newberry Library in 1918 and president of the board in 1928, a position he held until his death. In his will, he provided funds for the construction of a music library at Newberry in memory of his mother. He was vice-president of the board of trustees of the Art Institute of Chicago, to which he donated many valuable gifts, and the Chicago Orchestral Association, where his legal expertise proved valuable when settling musicians' labor disputes. Oakley was also director of the Chicago Civic Music Association, an executive member of the Chicago Council on Foreign Relations, and a one-time president of the Illinois Bar Association.
Horace S. Oakley was a prominent and respected member of Chicago society. He never married. He died at sea, en route to Italy, on December 15, 1929. In his will, he left a bequest to each of the organizations with which he was officially connected. At the time of his death, his closest relative was his half-sister, Mary Oakley Hawley of Washington, D.C., and Madison, Wisconsin.
