Gearan served as Massachusetts’ Director of Federal State Relations under Governor Michael Dukakis from 1983 until 1988, when he joined the Dukakis for President campaign. He acted as coordinator for the Iowa Caucuses, and national press secretary to the campaign. Following the 1988 election, Gearan returned to his position in the Office of Federal Relations until 1989, when he left to take a position as the Executive Director of the Democratic Governor’s Association, where he would serve until 1992. Gearan worked with candidate Bill Clinton during the 1992 campaign, and served as Vice Presidential candidate Al Gore’s campaign manager. After the election, he was appointed White House Deputy Chief of Staff, and Director of Communications and Strategic Planning.