This study explores Tsypkin`s unique novel Summer in Baden-Baden, which records the life and literature of Dostoevsky and is described by Sontag as one of the most "beautiful, exalting, and original achievements of a century`s worth of fiction." Dostoevsky in Summer in Baden-Baden is the incarnation of the complex and morbid pride. He is not properly communicate with others in daily life and literary circles, and always complains and condemns them just like an hero ``underground man`` in his Notes from Underground. The problem is that a Russian Jew Tsypkin is still keen on Dostoevsky although the great writer`s evildoing and anti-Semitism. "Why was I now on my way to Petersburg-yes, not to Leningrad?", "Why was I reading this book [Anna`s Dairy] now?" Tsypkin`s train travel from Moscow to Leningrad is the process to answer these questions, and a journey to find ``myself``. Going on pilgrimage to pursue Dostoevsky-human, Tsypkin continues to pay attention to the suffering of Anna, Russian Women and Jews, which represents the metaphor of human suffering. For Tsypkin in loneliness and helplessness, Dostoevsky is a irresistible being complicated by hate and love, literary revenge and homage. In the most difficult time of his life Tsypkin grapples with Dostoevsky and resists to him with a writing as if Dostoevsky grapples with a God who allows the suffering of children. In Summer in Baden-Baden Tsypkin recreates the memories of other`s suffering by an literary imagination for self-healing and regiment of suffering.