Is there a compelling normative case for value pluralism? Would we be better off in a world of irreducibly diverse and sometimes tragically conflicting values rather than one in which our values fit harmoniously together? This article identifies, examines and evaluates a normative argument for value pluralism suggested in Isaiah Berlin’s sessays on the history of ideas and particularly on Russian writers – that is, that deep conflicts of identity bound up with conflicting values sometimes contribute critically to the creation of great works of art, philosophy, and politics. Berlin attributes such deep identity conflicts to a range of important European historical figures, from Marx and Disraeli to Tolstoy and Turgenev to Hamann and Mill, and argues that their works of creative genius were motivated in part by the need to transcend their internal conflicts. On his interpretation, value conflicts appear to have been a necessary condition for their great works. In so far as we value these great creative works, it would then appear that we have a reason for embracing the underlying plurality of values that made them possible. But Berlin never linked these insights to his case for value pluralism or political liberalism. This article ends by evaluating those potential linkages. It concludes that there is a good reason that Berlin did not explicitly build a normative argument for value pluralism on these great works: on careful examination the argument reveals a paradoxical quality that at least partially undermines his critique of monism. By consequence, the argument from great works does not lend support to Berlin’s famous defense of pluralist liberalism, but rather to a form of creative liberalism that does not need to choose between pluralist sensibilities and monist aspirations.