And so it was interesting for me to find myself very enamored of a Republican president, but Ronald Reagan was someone I thought captured the spirit of America.

In 1999 Gillespie worked as the Press Secretary for the Presidential campaign of John Kasich until his withdrawal from the race. He served as Chairman of the Republican Party of Virginia from December 2006 to June 2007. [citation needed]
In April 2012 Gillespie was appointed as a senior advisor to Mitt Romney's 2012 presidential campaign.

Gillespie along with Jack Quinn former Chief of Staff to Vice President Al Gore founded Quinn Gillespie & Associates a bipartisan lobbying firm. Gillespie is an American Republican political strategist senior advisor to Mitt Romney 2012 and former Counselor to the President in the George W. Edward W.