ABSTRACT Isaiah Berlin viewed value conflict as tragic, as it requires the sacrifice of some values for others. It is a mark of maturity, he thought, to accept this tragic truth. This view raises certain conceptual problems that can be attributed to Berlin’s subtle departures from the German authors (Kant, Schelling, and Hegel) who originated the doctrine of tragic maturity—figures who had, in turn, transformed the earlier idea that enlightenment is a natural and morally neutral process of maturation. Kant moralized the notion of enlightened maturation by portraying it as contingent on our courage to bring it about, such that we are responsible if we remain immature. This theory of maturity rested on the idea, which would have been uncongenial to Berlin, that we are intelligible creatures inhabiting the noumenal realm, duty bound to exercise moral freedom, even though this duty surpasses our ability to carry it out, as we also inhabit the phenomenal realm, where our natural inclinations tend to make us resist laboring to fulfill our duties. However, according to Kant, the metaphysical limitations we face as individuals can be transcended to an extent, allowing us to make moral progress as a species—so long as we do not lazily persist in our immaturity. Schelling built upon Kant’s notion of freedom to bring out the tragic and heroic dimension of individual moral life, where the tragedy is our doomed but noble struggle to exert moral freedom in a world of natural necessity. Hegel turned these metaphysical notions in a more recognizably Berlinian direction by extending Schelling’s account of tragic conflict to conflicts of values. But he identified the ultimate tragic hero as an ethical totality that enacts eternal justice by reconciling such conflicts, while Berlin attempted to repudiate both the notion of a historical totality and the possibility of reconciliation on empirical grounds, even though these are metaphysical claims. Thus, Berlin asserted the absolute, trans-historical necessity of tragic value conflict, while the evidence for this assertion was merely his personal conviction that in his particular time and place, specific values were, as a matter of empirical fact, tragically irreconcilable. In this manner he illicitly portrayed Cold War value pluralists (such as himself) as courageously accepting the tragic inevitability of value conflict, while Marxists, the legatees of Hegel and thus German Idealism, immaturely shrank from this reality by embracing the fantasy of total reconciliation.