Riley discusses his successful campaign for Mayor of Charleston in 1975. Charleston's long-serving mayor, J. Palmer Gaillard had resigned in April 1975 to accept President Ford's nomination to serve as Deputy Assistant Secretary of the Navy for Reserve Affairs. State Representative Robert R. Woods endorsed Riley after considering his own bid for the mayor's office. Riley also discusses transitioning from state to municipal politics and asserts that he had only intended to serve one term. Rileys involvement in Charles "Pug" Ravenel's unsuccessful gubernatorial run the previous year introduced him to David Rawle, a New York-based media consultant. Rawle agreed to work on the Riley campaign and remained among the mayor's closest associates over the course of his forty years in office. Riley also shares his memories of businessman and civil rights leader Esau Jenkins as well as his first serious political opponent, Nancy Hawk. He concludes with reflections on his family's involvement in the campaign.
Riley discusses his close ties to Hillary and Bill Clinton. Riley discusses meeting and supporting Bill Clinton during his presidential campaign. Clinton returned the favor and assisted Riley to keep the federal courthouse downtown. Riley also discusses his discovery and enthusiasm for Barack Obama. Riley explains his support for Obama over Hillary Clinton in 2008. He asserts that he has maintained a positive relationship to the Clintons despite opposing the administration's decision to close the Charleston Navy Base. He acknowledges that the campaign to keep the base open distracted him from his campaign for governor in 1994.
