In this enlightening discussion, Sam Tanenhaus, a biographer and historian renowned for his work on conservative thought, delves into the life of Bill Buckley. Tanenhaus uncovers how Buckley’s elite yet turbulent upbringing shaped his views and political ideologies. They explore Buckley's isolationism even post-Pearly Harbor, his conflict with Gore Vidal, and the striking parallels between Buckleyism and modern Trumpism. With captivating anecdotes about Buckley’s personality, education, and family dynamics, this conversation offers rich insights into American conservatism.