This chapter considers the life and work of R. Judah Ashlag. Well known for his voluminous commentaries on the Zohar, Ashlag has, until recently, been largely dismissed by the scholarly community. The chapter begins with discussion of recent scholarly efforts to rehabilitate his image. It then proceeds to examine less appreciated elements of Ashlag’s thought. Namely, the libertarian socialism that he defended on religious grounds. Analysis begins with a discussion of Schopenahauer’s influence on Ashlag and the way that the kabbalist addressed Shopenhauerian pessimism by introducing a dichotomy of wills. Not merely a directionless force, will is subject to a dialectic: a divine will to give, a creaturely will to receive. This distinction leads to a moral division between egoism and altruism. Like Schopenhauer, who envisioned a mystical or mythical overcoming of the ego, Ashlag advocates mystical connection to God. Ashlag’s use of the dichotomy between egoism and altruism to critique state socialism and to promote libertarian socialism grounded in religious insight and practice is then addressed. The chapter concludes with a discussion of Ashlag’s understanding of Jewish nationalism and the Jewish mission as informed by his theology.