This chapter traces the development of the unfortunate relationship between the historical figures of Hannah Arendt and Isaiah Berlin. It explores Arendt's and Berlin's life stories and reconstructs the relevant contexts to illuminate the two thinkers' ideas and their comparative strengths and weaknesses. The chapter also elaborates their ideas in the abstract, bracketing the contexts in which these were produced, circulated and consumed. The chapter discusses a set of fundamental issues that simultaneously connected and divided the protagonists. They connected in that they were central to both Arendt's and Berlin's thought; and they divided in that they were answered by the two thinkers in conflicting ways. The chapter then assesses the two thinkers' individual arguments on their own merits, instead of supporting either of them indiscriminately.