Through an analysis of the chapter "The Legend of the Grand Inquisitor" in Dostoevsky's The Brothers Karamazov, this paper reveals the significance of two core concepts: Freedom and Authority. There are three hidden, self-enclosed and simultaneously inter-related dialogues in "The Legend of the Grand Inquisitor": between Ivan and Alyosha, the Grand Inquisitor and Jesus, and finally Dostoevsky and his potential readers. Through an exploration of these three relationships, and particularly bearing in mind a Gnostic perspective, this paper reveals the essence of the genuine religious conviction and the Grand Inquisitor's true identity as a philosopher, in order that the reader may understand the intentions of Dostoevsky in this self-standing chapter: i. e. an exploration of how the relation between philosophy and religion, or between dialectics and revelation, has always been, or "should be," in tension. The very relationship between the philosophers and God-man is irreconcilable-but how should philosophers within a certain political community deal with such Irreconcilability? This irreconcilability deserves our attention.