While many eschatological texts serve as consolation, moral or theological exhortation, and explanations about the nature of the world, the rabbinic eschatological narratives in this paper demonstrate that eschatology may play other and even opposite roles for a religious community or body of literature. The rabbinic texts in this paper treat the eschaton as a setting that is full of ambiguity and complexity, rather than clear answers. We see the eschatological context of these rabbinic narratives functioning as an arena in which the rabbis pushed their theological and ideological envelopes in surprising ways. The appeal of eschatology, particularly for the rabbis, comes into focus in this analysis. Eschatology frees the rabbis from the constraints of, as it were, polite conversation. There are various other ways in which the rabbis made themselves comfortable speaking in this way. One was to put words into others' mouths: others like God, or biblical characters, or fictionalized non-Jews in the Greco-Roman or Persian worlds in which the rabbis lived. Another way they did this was to set a narrative in the eschaton. They capitalized on this discourse's relation to a different reality that had not yet arrived and that they did not appear to expect anytime soon. In other words, rabbinic eschatological narrative served, at least at times, as a rhetorical "safe space" in which the rabbis could articulate and leave unresolved some of their deepest anxieties and self-criticism.