Avi Mintz (2008) has recently argued that Anglo-American educators have a tendency to alleviate student suffering in the classroom. According to Mintz, this tendency can be detrimental because certain kinds of suffering actually enhance student learning. While Mintz compellingly describes the effects of educator's desires to alleviate suffering in students, he does not examine one of the roots of the desire: the feeling of compassion or pity (used as synonyms here). Compassion leads many teachers to unreflectively alleviate student struggles. While there are certainly times when compassion is necessary to help students learn, there are other times when it must be overcome. Compassion in the classroom is a two-edged sword that must be carefully employed; and yet it is often assumed that it is an unequivocal good that ought to trump all other impulses. In this article I hope to raise awareness concerning the promises and pitfalls of compassion in education by examining the theories of two historical figures who famously emphasised compassion in their philosophical writings: Jean-Jacques Rousseau and Friedrich Nietzsche. Rousseau and Nietzsche argue that compassion is a powerful educational force but that it must be properly employed. For Rousseau and Nietzsche, compassion is necessary to develop self-mastery in human beings—the ultimate goal of education—but it is a compassion that must hurt in order to help. My hope is that Rousseau's and Nietzsche's ideas on compassion will encourage thoughtful reflection on the uses and abuses of compassion in education.