Bailey served as State Highway Commissioner beginning on January 17, 1939, alongside George Meacham and Sandy Singleton.
[2][3] Bailey was an opponent of the unionization of the Oklahoma City Police Department.
After being told by Bailey that such an attempt would lead to their firing, the officers disbanded.
[2] Bailey left the city manager position on February 1, 1944, and the following day he became Chief Engineer of the Oklahoma Highway Department.
[5] Bailey became the General Manager of the Oklahoma Turnpike Authority on January 13, 1951.