Fyodor Dostoyevsky is widely regarded as the greatest 19th-century Russian writer and a giant in world literature. He is familiar to literary-inclined psychiatrists for his rich and accurate portrayal of mental illness in several of his works. But his own chronic addiction to gambling and its consequent perils are less well-known. This article discusses The Gambler, one of Dostoyevsky's early (1866) semi-autobiographical novellas, inspired by his own addiction to roulette, focusing on its depiction of gambling. To better understand Dostoyevsky the gambler, the article also presents brief excerpts from letters that he wrote to his wife in 1867, when his gambling addiction appears to have been at its worst. Finally, the relevance of the central theme of this work, gambling addiction, to the present-day psychiatrist is discussed.