On the basis of mostly unpublished sources, the author reconstructs the life of the Hungarian writer Viktor von Dirsztay who was personally acquainted with many expressionist artists and writers, e.g. with Karl Kraus, Oskar Kokoschka, Herwarth Walden, Walter Hasenclever, Hermann Broch and Arthur Schnitzler. This association puts Freud into closer proximity with the cultural avant-garde of his times than previously realized. Between 1910 and 1920 Dirsztay underwent several phases of analysis with Freud; then he was treated by Theodor Reik. The overall length of his analysis with Freud is almost unparalleled. The article discusses whether and in which way Dirsztay's writings might have been influenced by his analyses and how Freud and Reik might have drawn upon their experiences with this patient. It is argued that likely references can be discovered in both authors' theories of masochism. There is an intriguing late remark of Dirsztay's that he was ‘ruined by analysis’.