Paul Cantor (1945 - 2022) was one of the preeminent Shakespeare scholars of our time as well as a great popular culture appreciator, critic, and teacher. We were fortunate to host Paul Cantor ten times on Conversations with Bill Kristol, covering the whole range of his interests. We are pleased to re-release his very first Conversation, in which Cantor explains why Shakespeare is a political thinker. Though we mourn his loss, we take some comfort in the fact that his work will continue to reach students of all ages, now and in the future.