This study evaluates the freedom/emancipation problem in a way based on the fact of alienation. Marx’s philosophical and historical approach is essential for this evaluation given the fundamental emphasis on alienation. Two figures who agitated Marx are important to comprehend Marx’s intellectual improvement; these are Hegel, in relation with spiritual progress, and Feuerbach, in relation with religion. Marx criticizes both and apprehends to alienation deriving from production activities and labor process, and, most critically, he emphasizes the historical mode of production that sets the framework of alienation. This concrete analysis facilitates to overcome alienation, and, after all, freedom/emancipation issue and the communism idea are discussed and affirmed this basic relationship.