The contradiction of freedom and determinism is always one of the core-problems across the two dimensions of theoretical and practical philosophy. The nodal point of philosophizing of this problem is of course the third antinomy of the “Transcendental Dialectic” of Critique of Pure Reason. This essay tries to research this antinomic problem through three dimensions: Conceptual-linguistic: from the western horizon, especially the Anglo-Saxon philosophizing of ordinary language, we shall analyze the three fundamental meanings of the concept of freedom: the freedom of movement, of action and of choice. Conceptual-historical: From the history of the genesis and development of dominant thinking-approach for this problem, i.e., from ancient Greek philosophizing to Kant, we shall underline especially the two different models, which are initiated each by Plato and Aristotle, and are transformed by rationalism and empiricism in modern age. Text-hermeneutical: in the context of the two dimensions mentioned above we shall re-interpret Kant’s model of the third antinomy in “transcendental Dialectics” of Critique of Pure Reason, that is, how Kant grasps intuitively and synthetically the conceptual-linguistic essence of freedom on the one side, and on the other side transform theoretically and creatively the existing models in the intellectual history of his time and conceptualize his own solution of the antinomy between freedom und determinism, in particular, the idea of transcendental freedom and the distinction of phenomenon and Thing in itself.