The essay discusses the literary-critical concepts of Matvei Kagan (1889–1937) – a Russian philosopher of Jewish origin, a student and follower of Hermann Cohen, Paul Natorp, and Ernst Cassirer, and a close friend of Mikhail Bakhtin in his early, constitutive period of the Nevel Circle (1918–1920). The concepts of love and bewilderment, as defined in Kagan’s works on Turgenev and Pushkin, are examined in the context of his philosophy of history, culture, and art. In the center of Kagan’s historical theory of literature lies the idea of the Jewish community as a model for canonization of the cultural work. Kagan views literature as generating self-awareness and national-cultural identity, either through tragic bewilderment at the loss of freedom and love in history (in the case of Pushkin) or through a culture’s self-defining dialogue with other cultures (as in the case of Turgenev). The central concept of this approach is that of svive-libe – “love of environment,” interpreted as love for a community’s cultural contribution in the context of its purposefulness in a universal human context.