This article explores a fundamental division among contemporary liberal internationalists regarding the relationship between state sovereignty and the goal of freedom. The article suggests that, in spite of his popular status among a wide variety of contemporary liberal international theorists, Immanuel Kant's political philosophy is an extraordinarily ambiguous ‘legacy’ because of the dualistic doctrine of state sovereignty to which he subscribed. Kant's thought is committed to state sovereignty while providing the grounds for a profound critique of its existence. The reason that sovereignty is ambiguous in Kant's political theory is that it is justified by his bifurcated understanding of human freedom.