The story of the early Zionist settlement in Palestine could be told from the viewpoint of failure and melancholia. An untold history of this period ignores the high rate of suicides and cases of clinical depression among the Zionist “pioneers”. The story of the forgotten author Israel Zarchi (1909-1947) will serve as a test case: During his short life he published six novels and seven collections of short stories, as well as translations from German, English, and Polish. He also became a close friend of Bialik, Agnon, Klausner and other literary and academic dignitaries of the Jewish Yishuv. His “Left-Wing Melancholy” was adopted by the young Amos Oz who mentions him as a key source of inspiration. Zarchi’s life and writing reflects his deep melancholy, the result of the growing gap between the high Zionist ideals and the reality on the ground.