This is a study dealing with the relationship between Leo Tolstoy and Vladimir Chertkov, the wealthy Russian aristocrat with connections at the imperial court. When the two first met in 1883, Tolstoy was suffering from a spiritual crisis due to this alienation from his family and was confirmed in the belief that the dissemination of his ethical and philosophical ideas was far more important than the creation of artistic works. Chertkov, deeply loyal to Russia’s autocratic rulers, openly challenged revolutionary violence with Tolstoy’s views and hoped to reform Russia morally and spiritually with the aid of the writer’s followers, the Tolstoyans. Chertkov’s energy in translating and promoting Tolstoy’s teaching all over the world was phenomenal. He eventually became the Tsar of the Tolstoyans since Tolstoy burdened with his marital life and advanced age was not interested in leadership. In the quest for a non-violent Russia, Chertkov displayed great personal courage and a firm adherence to Tolstoyan principles during the Soviet period.