Jesús Castellanos is a thinker (1879-1912) of philosophical transition, who is necessary to study in order to understand the social change that takes place in Cuba in the XX Century, due to the fact that he insists, as a reflexive subject, in a new way of philosophing. He is an intellectual of partial rupture with the positivism, and he uses philosophy to think in political and cultural terms, as one of the great contributions of Castellanos to the Cuban thinking. The objective of this paper is to demonstrate through a critical-analytical study the role of Jesús Castellanos´ philosophical thinking in the social context of the first decades of the Cuban republic. The main methods used are the hermeneutics and source criticism. The contribution of this research lies in the fact that it goes deeper into the philosophical speech of Jesús Castellanos that allows to define him as the owner of a cultural and political thinking committed to the fate of the nation from the axiological and anthropological renovation. The impact of this topic has to do with the critical approach of the foundations of our philosophical thinking and the rescue of the polemics around the national problem. To critically study these proposals are a strategy to explain the current Cuban thinking, giving it strength and functionability. The current significance of his philosophical contributions are seen in the fact that they take part of an alternative to the practice and the philosophical theory, whose main function is the social liberation of men.