This chapter examines how American Jews of the 1920s and 1930s struggled over the use of the Yiddish language. It considers the debate over the “fate” of Yiddish culture in the United States during the period in light of the lull in new arrivals during World War I and the eventual closing of the gates to unrestricted immigration in 1924. It also explains how most Americanizing Jews looked increasingly to the Hebrew language rather than Yiddish even as they continued to celebrate the linguistic aspect of their heritage. Finally, it analyzes the responses of eastern European Jewish immigrants and their children to the increasing shift from Yiddish to the English language, along with efforts to create a new Jewish literary culture aimed at native-born American Jews.