The Thesis deals with literary works of Dostoyevsky and Jenko, dealing with motives of gambling, including prior similar tradition in Russian romantism, namely two prominent works of Pushkin, The Queen of Spades and Eugene Onegin, which had a great impact on both later realistic approach to literature as well as on gambling as a literary motive. According to several works of both authors' opuses, the Thesis analyses, compares and researches the excerpts dealing with gambling, and how these elements reflect private life of both authors. This includes the outline of some characteristic features, prominent in their biographies and which certainly affected later gambling addiction. The Thesis uses the perspective of prominent literary critics (Leonid Grossman for Dostoyevsky) and the perspective of authors' family members/partners. The Thesis describes one of the most prominent gambling 'systems', namely Martingale, which had and still has quite an impact on betting psychology. The main goal of The Thesis is introducing the reader to motives of gambling in literary tradition of realism, and finally to point out, where and how these motives reflect in present, how to define them, deal with them and, when neccessary, how to search for proffesional assistance.