The retranslation hypothesis is a theoretical concept introduced to translation studies by Berman (1990), Bensimon (1990) and Gambier (1990). The hypothesis is based on the premise that retranslations tend to be closer to the source text and more foreignizing in nature, while initial translations aim to bring the source text closer to the target audience by domesticating it. Some of the studies conducted so far have managed to confirm the retranslation hypothesis while others demonstrated ambivalent results with regard to the validity of all aspects of the retranslation hypothesis as well as its applicability to all types of texts. The aim of the current thesis was to examine whether the hypothesis is applicable to a radically modernist text such as James Joyce's 1922 novel Ulysses. A comparative analysis of textual segments from two existing translations of James Joyce’s novel Ulysses into Croatian, the 1957 translation by Zlatko Gorjan and the 1991 retranslation by Luko Paljetak. was carried out. Translation strategies used in the texts were identified and sorted according to Andrew Chesterman’s classification of translation strategies (2016), and their frequency was used as the first parameter of closeness. Due to the expressive-aesthetic function of the text studied, closeness was also measured in terms of preservation of instances of creative language. The contradictory nature of the findings with regard to the two observed parameters pointed to the conclusion that the retranslation hypothesis does not provide a sufficiently comprehensive methodological frame for studying the phenomenon of retranslation. The thesis calls for each translation and retranslation to be observed individually and with respect to the type of the language of the texts involved as well the context in which they were created.