ABSTRACT Isaiah Berlin’s “Two Concepts of Liberty” lecture was the iconic statement of Cold War liberalism, an expression of all its insights and limitations. It divided critics then and now: was it a stimulating restatement of classical liberalism with revitalising potential for post-war democracy or a conservative retreat from politics that paralysed liberalism as both a social and political force? This article approaches the debate from a side angle. It looks at how the Freedom anarchist group addressed the problems raised by the lecture. Of all ideologies, anarchism most elevated liberty as the highest good. At the same time, it considered itself a social movement for the advance of liberty. As such, the tension highlighted by “Two Concepts”, between the intrinsic value of liberty and the pursuit of liberty, had long preoccupied generations of anarchist thinkers but never more so than after the War, where inherited assumptions about revolution and social change became implausible. Although Berlin identified anarchism with the fullest realisation of positive liberty, the movement was more philosophically diverse than he recognised. The Freedom group’s responses to his dilemma of liberty demonstrates this. At the same time, their efforts to think beyond the impasse and experiment with new forms of political practice – as exemplified by Anarchy, Freedom’s sister publication – outstripped those of the liberals casting fresh light on the limits and possibilities of freedom in a Cold War world.
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