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Walter Benjamin (1892–1940) and Gerhard Scholem (1897–1982) were bound by a deep friendship, intertwined since 1912 and continuing until 1940 when Benjamin committed suicide in Port Bou, terrified of being handed over to the Nazis. The two intellectuals, both of Jewish faith, made different existential choices: Benjamin remained in Germany until the racial persecution of the Nazi regime forced him to roam around Europe, while Scholem settled in Palestine and worked at the University of Jerusalem, where he could devote himself to the study of Jewish mysticism. This essay concerns the correspondence between the two scholars, particularly on Benjamin’s proximity to communism, and his relationship with the scholars of the Institute of Social Research (directed by Max Horkheimer) and with Bertolt Brecht. Against the backdrop of this correspondence, Benjamin’s attempt not to give up his intellectual research and friendship is clearly visible, even though he was forced to look for marginal and peripheral places where he could survive in a Europe given over to Hitler’s wars.