Lucy Cane presents the first full-length study of Sheldon Wolin (1922–2015), an influential theorist of democracy and prescient critic of "inverted totalitarianism" in the United States. She traces the development of Wolin’s thinking over sixty years, offering an overarching interpretation of his central preoccupations and shifts in perspective. Framed around themes of loss and mourning, this is not only an intellectual biography, but also a critical engagement of Wolin’s work with democratic theory more broadly and an assessment of its value for addressing contemporary crises of democracy. Cane brings Wolin into conversation with other contemporary theorists, from Chantal Mouffe to Edward Said, as well as with his direct intellectual influences.She argues that his mournful tendencies continue to offer unique insight into the potential loss of local democratic cultures in an era of neoliberal precarity. At the same time, she questions whether his politics of mourning can adequately grasp the dynamics of democratic coalition-building or the value of new political movements and ideas. Sheldon Wolin and Democracy remedies a lack of interpretive studies of this key thinker, connects divergent strands of contemporary theory, and addresses urgent democratic dilemmas. It is a must read for all political theorists and others in the academy and beyond who seek to conceptualize the fate of democracy amidst the rise of right-wing populist movements in the twenty-first century.