This paper seeks to rethink the question of freedom in relation to the social democracy of the past, present and future. Here I argue that much contemporary debate on European social democratic Left emphasises a communitarian agenda. Despite some of its strengths it is problematic in terms of its neglect of questions of freedom and more global concerns. Here I return to the liberal socialism that emerged within Europe in the context of totalitarianism. Questions of freedom were emphasised in this context, and can be productively returned to in the new dimensions of the present. In particular I focus on the 'cultural' socialist writing of the 1940s and argue that thinkers like Fromm, Orwell and Roselli have something to say to us today. At this point I consider whether the neoliberalism of the present shares certain features with the authoritarian ideologies of the past. Further I seek to critically assess more recent developments in ideas related to the potential emergence of a cosmopolitan Europe. Finally in the context of the social and ecological crisis of contemporary Europe I seek to highlight how we might begin to rethink questions of freedom in ways which might help socially.Keywords: Freedom, democracy, socialism, totalitarianism.