A key concept on which our understanding of democracy relies is freedom. Yet freedom has recently also become something of an embarrassment to the global Left, a notion more easily appropriated by the Right, in its defense of individual rights in contrast to shared social norms. I would like to reflect on what a robust idea of freedom for the Left might look like, and why it is necessary to recover it, rather than trying to do away with it. And I want to raise that question in a way that urges us to reflect on both micro-history and macro-history: how world historical events shape and constrain the lives of individuals who happen to be caught up in them, and how existing political institutions try and fail to promote certain moral ideals.