Learning about the human condition through Greek tragedies offers a dynamic way for medical students and professionals to reflect on their own experiences. In this article, we discuss Philoctetes by Sophocles, which depicts an example of human vulnerability and offers powerful lessons on the nature and taxonomy of pain. We describe how we used the lessons learned from Philoctetes to empathize with the different types of pain experienced by a patient with heart failure at a student-run clinic. We hope that our experience using Greek tragedy to foster stronger patient-provider relationships and improve treatment outcomes encourages other medical students and healthcare professionals to use the humanities to inform our role as healers.