In this interview, James S. Vlasto discusses key developments in the political career of Puerto Rican leader Herman Badillo from 1969 until the mid-2000s, covering three of his mayoral campaigns and his election to the House of Representatives. Vlasto met Badillo in 1969 when the politician was running for the first time as a candidate in the Democratic primaries for New York City mayor. Vlasto was immediately hired by Badillo as his press secretary and since then their professional and personal relationship extended for over 40 years. He explains in detail the factors that influenced Badillo’s political achievements and failures such as facing resistance within the Democratic Party and dealing with limited funding. He also describes the relationship between Badillo and the media over the course of his multiple campaigns, the response the constituency and other politicians had to Badillo’s leadership, and Badillo's role as mediator during the Attica Riots in 1971. Finally, Vlasto talks about his personal life and how he became involved in journalism and later on in politics.