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The Russian-Jewish religious thinker Lev Shestov (1866–1938) has returned from obscurity in the post-Soviet revival of religious and philosophical thought in Russia. Despite his reputation as an anti-modern irrationalist, his heritage is of key relevance to contemporary currents in Russia and the wider world; we here explore the implications of his contribution in religious, social, philosophical and literary-cultural contexts. In particular, we trace Shestov's relation to post-modernism in various settings. We explore the connection between his thought and the conflict between moral principles and scientific advance, and argue that his existential perspective is a precursor to anti-globalism. We expose a link between the apophatic theology that underlies modern Russian religiosity and the Hassidic tradition which, arguably, influenced Shestov's thought, and show the relevance of his premonitions to contemporary religious developments in Russia.