In realistic novels we come across characters that are committed to true, authentic values and principles. According to George Lukacs, who finds realism the cornerstone of literature and Lucien Goldmann, who derives directly from Lukacs and finds each and every work conformed with realism of great value, the problematic hero, is transcendentally homeless, unable to bring inner and outer reality, society and personality into a meaningful unity and seeks to transform the modern values and resurrect their lost authenticity. Goldmann, in order to illustrate a rigorous homology between structure in classical novel and the structure of exchange in market economics states that novel as a social product is shaped by social and cultural forces. Because the modern period is heavily influenced by capitalism, the values of capitalism are ingrained in modern works. A hero, who tries to search degradedly for authentic but inaccessible values in a degraded world, will eventually be doomed to failure. Dostoevsky’s The Gambler is in particular a clear example of the non-economic but value-based relation to money in the novel. The current article aims to shed more light on how the problematic heroes of The gambler, appear as sadistic and masochistic sellers and buyers; abandon the authentic values and turn money into the obsessive object of their interest.