High Quality Content by WIKIPEDIA articles! Robert L. Flanagan was the Secretary of the Maryland Department of Transportation from 2003 until 2007, under the administration of Governor Robert Ehrlich. Prior to this position, Flanagan served in the Maryland House of Delegates. He was first elected to office in 1987 and served with fellow Republican, Robert Kittleman, until 2002, when the districts were redrawn and he would move to District 14B.