Moses Maimonides was a rare kind of radical. Being a genuine Aristotelian, he recommended following the middle path and avoiding extremism. Yet, within the sphere of Jewish philosophy and thought, he created a school of philosophical radicalism, inspiring Rabbis and thinkers to be unwilling to compromise their integrity in searching for the truth, regardless of where their arguments might lead. Both Spinoza and Salomon Maimon inherited this commitment to uncompromising philosophical inquiry. But of course, such willingness to follow a philosophical argument to any length is a fine prescription for getting into trouble with community and political leaders. In this paper I will trace the story of one such collision, which took place between the radical philosopher Salomon Maimon and the bourgeois Enlightenment politician, Moses Mendelssohn.