George Thomas Conway III as Self - Attorney, Co-Founder The Lincoln Project

Malcolm Nance as Self - Former Intelligence Officer

John Gartner as Self - Author, Psychologist

Lance Dodes as Self - Psychiatrist, Psychoanalyst

Justin Frank as Self - Psychiatrist, Psychoanalyst

Anthony Scaramucci as Self - Entrepreneur, Political Consultant

William Kristol as Self - Republican Political Analyst

Richard Painter as Self - Ethics Attorney for George W. Bush

Ruth Ben-Ghiat as Self - Historian, Author 'Fascist Modernities'

Cheryl Koos as Self - Historian, Professor of Interwar European History