Karl Kraus was one of the most important and influential personalities in Vienna at the end of the 19th century and the beginning of the 20th century; he was the founder and life director of the magazine Die Fackel, famous for leading important debates with writers, poets, journalists, and psychoanalysts. At the beginning of the 20th century, Freud wanted to win Kraus's sympathy because he believed that having him on his side was essential for psychoanalysis to penetrate the artistic and cultural circle of Vienna. As will be shown in this article, the alliance between the two was never consummated and, on the contrary, they became antagonists, with Ernst Jones naming Kraus “Freud's greatest enemy.” In this paper, mentions of Freud and psychoanalysis in Die Fackel between 1905 and 1930 were identified and subsequently, 26 aphorisms written by Kraus through the post-structural linguistic approach were analyzed. A sample from the digital collection AAC-FACKEL of the Austrian Academy Corpus was used. Early writings reveal that Kraus came to regard psychoanalysis as an ally in his struggle against Austrian sexual morality, yet he was always wary of its invasion of the intimate lives of individuals. Kraus criticized Freud's explanation of female hysteria and instead considered that the root of female suffering was due to their inability to give themselves individuality. It can be concluded that although Kraus was a severe critic of psychoanalysis, at many times he viewed some of its postulates with sympathy, to the point that he considered his aphorisms to be a kind of attenuated psychoanalysis; that is, without the exaggerated presence of sexual elements or interpretations.