In this philosophical-theoretical study of Lev Tolstoy’s pedagogical legacy of his Yasnaya Polyana school in the Russian Empire (1859–1862), I raised three major questions: (1) was Lev Tolstoy a democratic educator, and if so, why can one claim that, (2) if so, what kind of a democratic educator was he, and (3) what kind of limitations to his democratic education have I observe and what were the sources of these limitations? My answer to the first question was unequivocally positive. I argue that Tolstoy was the conceptual founder of democratic non-coercive education and the first known practitioner of democratic education for children. In my view, his democratic education was based on educational offerings provided by the teachers. His democratic educational philosophy was based on non-coercion, naturalism, anarchism, liveliness, pragmatism, pedagogical experimentation, student responses, pedagogical self-reflection, and dialogism. At the same time, his democratic education was limited to his uncritical acceptance of conventionalism. Tolstoy’s attraction to Progressive Education was facilitated by ignoring his enormous powers, both explicit and implicit, that he manifested exercised in the school and enacted through his “pervasive informality.” In my judgment, Tolstoy overemphasized pedagogy over self-education and did not distinguish learning from education. Still, Tolstoy’s pioneering work in democratic education, both in theory and practice, remains mostly unacknowledged and unanalyzed while continuing to be highly relevant and potentially influential.