Following the resignation of W.A. Quinn, H.E. Bailey assumed the position of City Manager on February 11, 1941. During his term, Bailey made great moves to support the war effort. Not only was Tinker Air Force Base appropriated and built as a $14 million air depot offering 3,500 jobs to workers, but Bailey also pushed for the construction of Wiley Post Airport as a relief for the Municipal Airport, laden with war-related air traffic.

Bailey later became director of the Oklahoma Department of Transportation. The H.E. Bailey Turnpike in southwest Oklahoma stands in his honor.