F. Scott Fitzgerald (1896-1940) is regarded as a great twentieth-century American novelist. In many ways Fitzgerald’s legendary life has had a huge impact on critics and readers in overshadowing his great work. The 1920s can be seen as a transition time with a great change in American history from the Victorian period to modern times and with the huge impact of World War I on people’s lives. It is only recently that critics have moved away from studying Fitzgerald’s work as that of a merely superficial and historical writer and examined his works in various other perspectives. In addition to historical and biographical studies, Freudian theory is an important approach to bring a new depth to our understanding of his work. In one of his great novels, The Great Gatsby, Fitzgerald depicts the traumatic losses of a self-made man, Jay Gatsby, who tries to win his idealized girl again. In this paper, the author aimed to examine the losses of Jay Gatsby in the light of Freudian theory to bring a new perspective on the protagonist’s trauma and psychological loss and the reasons why he never escapes from his illusive world.