At Princeton, Wolin led a successful faculty effort to pass a resolution urging university trustees to divest from endowment investment in firms that supported South African apartheid.
He pays particular attention to how the latter contribute to the changing meanings of a received political vocabulary, including notions of authority, obligation, power, justice, citizenship, and the state.
Cornel West has called it Wolin's masterpiece, the crowning achievement of “the greatest political theorist of and for democracy of our time.”[10] In essays dealing with major thinkers of the recent past, including some of the most formidable bodies of work of the twentieth century, Wolin probed different approaches to both understanding the nature of theory and its bearing on the political from a perspective clearly aligned with the principles of participatory democracy.
From this perspective, Wolin engaged with a vast array of thinkers: Theodor W. Adorno & Max Horkheimer, Hannah Arendt, John Dewey, Michel Foucault, Leo Strauss, Harvey C. Mansfield, Karl Marx, Friedrich Nietzsche, Michael Oakeshott, Karl Popper, John Rawls, Richard Rorty, and Max Weber.
[11] Politically, Wolin penned essays on a variety of themes and figures, including terrorism, conservatism, Jimmy Carter, Henry Kissinger, and Ronald Reagan.
His The Presence of the Past offered an original critique of Reaganism, its discourse and practice, and a series of searching reflections on the bicentennial of the American Constitution.
His last book, Democracy Incorporated (2008) formulates a scathing critique of the administration of George W. Bush and its war on terror and a plea for the recovery of democratic values and practices.
In his effort to think about the fate of democracy in the United States, he formulated a novel theorization of modern and postmodern forms of power and how these shaped the limits and horizons of political life in the late twentieth and early twentieth-first centuries.
Wolin flew 51 different combat missions serving in the South Pacific, specifically the islands surrounding the Philippines, during World War II.
This tactic was incredibly risky, as the B-24 was a "big, lumbering aircraft" which was hard to manoeuvre, and not infrequently "proved disastrous" for the crews of these planes, costing the lives of many of Wolin's fellow airmen.