Sholem Asch was a prominent Yiddish author and dramatist of the first half of the twentieth-century. He was at the pinnacle of his writing career in 1939 when he published The Nazarene, the first of his three novels on New Testament themes. The Yiddish press refused to publish the novel and its first appearance in its English translation only intensified the controversy. Despite support from certain Jewish intellectuals, Asch was accused of apostasy, proselytisation, and for trying to appease the Christian world with an eye on the Nobel Prize. Asch asserted that his aim was reconciliation between Judaism and Christianity which he viewed as being parts of a single whole, a task which he saw as being of utmost importance in a climate of growing anti-Semitism, a modern manifestation of almost 2,000 years of Christian anti-Judaism. To this end, Asch wrote two more novels on New Testament themes—The Apostle (1943) and Mary (1949). This thesis explores Asch’s interpretation of the stories around the emergence of Christianity and how he uses the genre of the Rewritten Gospel to address Christian anti-Judaism. It especially studies his depictions of Jesus whom he firmly situates within the Jewish tradition keeping with the wider movement for the Jewish reclamation of Jesus that followed the European Enlightenment. This study draws on modern scholarship on Second Temple Judaism and Early Christianity as well as Jewish-Christian dialogue to locate Asch within the discourse and explicate Asch’s possible contribution to it. It also examines how Asch introduces complexity and diversity within the accepted narratives of ancient texts which were written in certain historical contexts and carry within them the needs and biases of that context. This thesis illustrates how Asch, being a fiction writer, transcends doctrinal limitations to provide alternate interpretations of the gospel narratives with the hope to foster better understanding between Jews and Christians. In doing so, he introduces hermeneutical possibilities which creates a space for rethinking identities in a pluralistic world and reminds his readers of the oft-forgotten power of stories to reshape humanity.