How does one teach a nineteenth-century Yiddish novel to twenty-first-century Canadian undergraduates? Can Jewish literature be of interest to nonheritage learners? The piece analyzes strategies of teaching of Letters of Menakhem Mendl written by the Ukrainian Yiddish writer Sholem Aleichem at the end of the nineteenth century. The trajectory of teaching the novel in the context of Jewish studies to the context of diaspora studies provides unexpected insight into the meaning of this text.