The latter investigation brought him into contact with Robert F. Kennedy in the late 1950s. The two men forged a strong working relationship and personal friendship, and in 1960, Seigenthaler helped to campaign for John F. Kennedy's presidential run. Shortly after the election, Seigenthaler declined a position as newly-appointed Attorney General Robert F. Kennedy's press secretary, preferring to keep journalism and politics separate. Still, he wanted to work for the administration, so he accepted a job as RFK's administrative assistant instead. During his short tenure working for the Justice Department, Seigenthaler played an instrumental role in negotiating with Alabama Governor John Patterson and Eugene "Bull" Connor for the safe passage of the Freedom Riders in 1961, which he describes in detail.
In 1962, Seigenthaler left the Justice Department to become the editor of The Tennessean. He speaks at length and in great detail about the changing nature of southern journalism during the 1960s and 1970s, paying particular attention to the impact of cultural homogenization and the corporate takeover of regional newspapers. According to Seigenthaler, during the 1960s and early 1970s, racism and poverty were not problems for the South alone but for the nation as a whole. In addition, Seigenthaler laments that the trend toward moderation in national politics would limit social justice activism. The interview concludes with Seigenthaler's commentary about Robert F. Kennedy's assassination and his role in Kennedy's 1968 presidential campaign.