George H. O'Connor was born on 20 August 1874 in the District of Columbia and attended St. Johns Academy in Alexandria and the National University Law School, where he received an LL.B. in 1894. He then attended Georgetown University as a special student, where he participated in musical and dramatic programs, and was awarded the LL.M. in 1895. He maintained a close connection to Georgetown thereafter, continuing to participate in banquets and musical programs with the Glee Club and as a soloist.
Mr. O'Connor was admitted to District of Columbia Bar in 1895 and to practice before the Supreme Court of the United States in 1915. He joined the District Title Insurance Company and was secretary and treasurer from 1900 to 1907 and title officer from 1907 to 1941. In 1941 he was promoted to President of the Company, and of the Washington and Lawyers Title Insurance Companies. He served on the boards of many civic committees and charity organizations, and participated in several clubs and associations.
George O'Connor also made many friends among prominent businessmen and members of the national government during his life in the District, especially through musical-comedy productions, which he continued to participate in throughout his life. He was called Troubadour to the Presidents, since he had performed for seven of them, from Taft to Truman. His last performance was for a dinner given by the Washington Bar for U.S. Chief Justice Fred M. Vinson, about a week before he died on 28 September 1946.