The Maimonidean Judaism proposed by thinkers such as Yeshayahu Leibowitz and (more reasonably) by Menachem Kellner does away with problematic essentialist views of Jewish choseness and demythologizes ritual aspects of Jewish tradition. However, it may also leave us wondering what is left for modern Jews to find relevant in their tradition. Leibowitz seems to deflate Judaism into an absurd existential decision to serve a unknowable God by performing otherwise pointless commandments, while Kellner risks leaving his readers to conclude that Judaism is an outdated vehicle for promoting universal values which, in any event, are already widely recognized in Western societies. I suggest that these weaknesses stem from an atomized, individualistic approach to Judaism which undervalues the role of the national community as the realizer of the Torah’s commandments and values. While the Jewish People’s unique religious role is covenantal and conventional and does not stem from some innate Jewish essence, that does not deplete its significance and emotional weight. After all, marriage, a central metaphor for the God/Israel relationship, is also “merely” conventional. I find evidence of the kind of “Romantic Maimonideanism” which I propose in the writings of R. Meir Simkha of Dvinsk (1843–1926) and suggest that his work was misappropriated by Leibowitz.