Tom Dent begins the interview by discussing his education in New Orleans, including at Gilbert Academy in New Orleans, where he attended high school. He describes quitting his graduate studies at Syracuse six credit hours short of a doctorate and never regretting that decision. He continues to discuss his early work as a writer, including some work in copy editing and journalism, as well as his own personal writing. He details how through interviewing Thurgood Marshall he went to work as a public information professional for the NAACP Legal Defense Fund. He mentions that the first issue of Umbra was typed at the Legal Defense Fund office. He describes this period as intense, but one that provided him with experiences such as traveling throughout the South; he observes that most of his best ideas were formulated during this period with Umbra and the Legal Defense Fund, and notes that he was financially strapped during this time. He explains that how a robbery of his New York apartment was one of the primary motivators for his ultimate return to New Orleans. He also notes his excitement in working with the Free Southern Theater (FST) in New Orleans. He also observes that he was in part hesitant to move back to New Orleans because he would be living under his father's shadow, though acknowledged that he would have to deal with that dynamic regardless of where he was living. He summarizes racial politics in New Orleans among Creoles and darker-skinned African Americans and describes the "Creole elite." He describes Creole identity as separate from both White and Black: "It was like an island that was floating more and more out to sea and becoming less connected to any other land"u2026 it became more illusionary and self-destructive." He compares African American Atlanta with African American New Orleans, making reference to his article on the topic in Southern Exposure. He talks about how churches and segregated schools provided rich opportunities for African American musicians coming out of New Orleans. He talks about jazz families in New Orleans, including the Marsalis, Lastie, and Neville families. He then discusses the Civil rights-era in New Orleans, including the role of organizations like SOUL in the Lower Ninth Ward. Rogers asks about the Free Southern Theater's role in the Civil rights Movement, and offers that the FST was not a local organization but tied more into a national artistic movement. He describes how African Americans had to overcome White power structures in employment, and how federal and city government jobs provided most opportunities for middle class African Americans in New Orleans. He details major changes to FST in the late 1960s, including becoming an all-Black troupe and their creation of performances for majority-Black audiences.