In Philosophy and Law, Strauss claims that the “medieval Enlightenment” had certain advantages over the “modern Enlightenment.” It is not easy, however, to articulate which problems he thought the medievals—his medievals, which he refers to as “Islamic and Jewish medieval philosophers”—might have superior “solutions” to. The title Philosophy and Law adumbrates what Strauss will eventually articulate as the title of one of his other books, namely, the problem of The City and Man (or man and city in the earlier title)—or the theologico-political problem. There are, however, at least two sides to this problem: the political solutions of the human problem, which are all necessarily less than fully adequate, and the philosopher's relation to the city or state. In recent scholarship on Strauss, a great deal of stress has been placed on the latter, that is, the large gap between philosopher and city that appears to be a mainstay of both premodern and, at least, early modern philosophy (cf. PAW, 7–8). Previously, a great deal of stress was placed on the former, that is, the discontinuity between the typically “ancient” and typically “modern” political solutions of the human problem—and thus the “problem of ancients versus moderns” in Strauss. The premodern political solution privileges some form of aristocracy or virtuous monarchy, even if tempered by realism about the need for a mixed regime, while the modern political solution is first typified in Spinoza as liberal democracy.

Based on what I know of his explorations of the medieval Enlightenment, I doubt that Strauss ever thought that the political solution of the medievals (or the ancients) was unambiguously superior to the political solution of the moderns. As he observed in his 1962 preface to Spinoza's Critique of Religion, “Finite, relative problems can be solved; infinite, absolute problems cannot be solved. In other words, human beings will never create a society which is free of contradictions” (SCR, 6). Strauss seems, however, to have detected in early modern political solutions the causes of deleterious effects for philosophy as a way of life in late modernity.