To define freedom as the absolute or Philosophy is a necessary prerequisite of understanding the political and social actualisations of freedom through history. According to Hegel’s articulation of philosophy, what makes philosophy a self-supporting realization of human freedom is that which is based upon the speculative thought (Speculation). Speculative thought is the process of philosophical actualization that is able to gather all contingencies within its own realm of freedom. Two approaches to interpret Hegel’s relation of philosophy and freedom are still dominant: First, the relation might be accepted as the enclosed totality of philosophy since Hegel’s practice of philosophy can conceptualize all actualized formations of reality; second, the relation might be criticized based on the supremacy of praxis over theory. In other words, the first approach considers philosophy as a closed totality; on the contrary, the second approach is based upon the supremacy of the power of unforeseen praxis over the power of interpretation. I attempted to propose a new way that would be another sort of reading Hegel’s understanding of the relation as a combination of unforeseen openness and an absolute totality at the same time. Accordingly, this article is a conceptual approach to explicate how philosophy is first and foremost able to conceptualize all historical realizations within its own totality as the last moment of the Absolute Spirit; second, how Hegel’s articulation of philosophy still remains a freely open totality to face new social and political realizations in the future.