In June 1988, President Reagan Tuesday tapped Oglesby to serve as White House Deputy chief of staff.[2] Oglesby succeeded Kenneth Duberstein, who had been promoted to the post of chief of staff, succeeding Howard Baker, who had resigned.[3]
From 1981 to 1986, Oglesby served in the White House Office of Legislative Affairs,[4][5] leaving to take a post as vice chairman of the board of Hect, Specer & Oglesby, Inc., a government relations firm in Washington.
Prior to his Legislative Affairs service, Oglesby was minority staff associate for the House Energy and Commerce Committee. He also served as deputy and acting director of the State of Illinois' office in Washington DC, and as Executive Assistant to Congressman Ed Madigan. Prior to coming to Washington, Oglesby served as an assistant to Governor Richard B. Oglivie and as executive assistant to the Speaker of the House W. Robert Blair.[6]