This article explores the rhetoric of regret as a way to rethink the aesthetic dimension of two hitherto artificially separated late ancient corpora of thought—rabbinic and “pagan.” Moving away from the thinking in terms of historicist “influences” I arrive at a point of mutual illumination of the corpora, thereby advancing a new model of philosophical and rhetorical analysis that both justifies the importance of the modern discussion of relationships between philosophy, rhetoric, and aesthetics for understanding the Talmud as a late ancient body of text and thought and shows how the Talmud, thus understood, complicates and raises the stakes in that discussion. I first draw on the framework of this bidirectional analysis for probing the rhetoric of the rabbis and of the “pagan” philosophers. I consequently work against the grain of a modern interpretation of late ancient aesthetics to arrive to a comparative study of the aesthetics of rabbinic discourse.

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