Damon and Francisco attempt to awaken the podcast from its dogmatic slumber by discussing a classic essay by philosopher Isaiah Berlin, "Two Concepts of Liberty". The essay is one of the most influential in recent political philosophy, and his conceptions of positive and negative liberty frame much of the discourse in the field. We discuss how this distinction leads to Berlin's defense of liberalism, whether his value pluralism leads to relativism, and debate if he's too harsh on positive liberty.