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Isaiah Berlin’s dichotomy of freedom is now the starting point of debates of freedom among intellectual historians and political philosophers. Berlin asserted that two sorts of freedom, negative one and positive one, were discerned in the Western political discourses. While negative freedom means the absence of other’s interference, positive one the realization of rational self through the participation in the course of communal decision-making of common goods. Berlin insisted that only the former was genuine freedom proper to liberal society. On the contrary the latter was the rhetoric of despotism and totalitarianism because it exacted sacrifice from individuals for community in the name of reason or common weal. We can agree with him on this dichotomy apart from his evaluation. The movie Matrix showed us two persons who represented these two sorts of freedom respectively. One is Cipher who pursued negative freedom to choose his own life regardless of reason or morality by betraying Mauphius. Another is Neo who practiced positive freedom to realize his rational self by taking part in Mauphius’s good cause of human liberation. Who is a really free person? Should one of them be ostracized in the name of freedom? The story this paper tells is to report how these two persons can be supported by two conceptions of freedom respectively. Cipher wanted to be free as we usually use the word free. Who could reproach him because he decided to live his own life if he did not commit a harm to Mauphius? Is it right to find out the dark side of freedom in Neo’s vita activa for common cause as Berlin did? How clearly can Berlin’s misunderstanding of positive freedom be evidenced by reading Spinoza and T.H.Green? The story does not end in concluding which freedom is real freedom only to open this question to readers.