Yosef Haim Brenner's complex legacy defies the simplistic dichotomy of martyr-saint versus self-hating critic of Diaspora Judaism, as revealed through his final novel *Breakdown and Bereavement* (1920), now accessible in Hillel Halkin's English translation. Through close textual analysis and biographical contextualization, this review uncovers Brenner's sophisticated engagement with archetypal allusions to Job, Jesus, and Ezekiel, reflecting his controversial openness to Christian theological concepts while maintaining fundamentally Jewish life-affirming conclusions. The protagonist Yehezkel Hefetz emerges as a paradigmatic Jewish intellectual grappling with sexual and ideological impotence in early twentieth-century Palestine, brought to life through Brenner's fragmented dialogue and stream of consciousness techniques. By integrating literary criticism with intellectual history, the analysis demonstrates how Brenner's avant-garde modernistic style and introspective, self-critical themes account for his enduring relevance compared to contemporary writers. *Breakdown and Bereavement* represents Brenner's mature artistic achievement, offering a nuanced portrayal of First Aliyah intellectual experience that transcends simple ideological categorization and establishes Brenner as a significant modernist voice in Hebrew literature.