This chapter traces Rahv’s role in forming the canon of 20th century Jewish writing: to use his words, works by writers of Jewish descent. It considers his championing of Franz Kafka, Isaac Bashevis Singer, Bernard Malamud, and Saul Bellow. The significance of modernism, Zionism, and Yiddish in their works is foregrounded. Their stories of Jewishness are interwoven with Rahv’s to illuminate his affirmation of Jewish language and culture, which was marked, however, with ambivalence and irony. To explain Rahv’s ambivalent Jewishness in the 1940s and 50s, this chapter considers what two of his closest friends and associates had to say about him: William Barrett and Mary McCarthy, whose satirical depiction of him in the 1949 “roman à clef” The Oasis provoked Rahv to initiate a law suit. The chapter closes with reflections on what Jewishness meant in Rahv’s world and my own during the 1950s.