The question why natural processes tend to flow along a preferred direction has always been considered from within the perspective of the Second Law of Thermodynamics, especially its statistical formulation due to Maxwell and Boltzmann. In this article, we re-examine the subject from the perspective of a new historico-philosophical formulation based on the careful use of selected theoretical elements taken from three key modern thinkers: Hans Reichenbach, Ilya Prigogine, and Roger Penrose, who are seldom considered together in the literature. We emphasize in our analysis how the entropy concept was introduced in response to the desire to extend the applicability of the Second Law to the cosmos at large (Reichenbach and Penrose), and to exam...