In the Nicomachean Ethics, Aristotle places the art of medicine alongside other examples of technē. According to Gadamer, however, medicine is different because in medicine the physician does not, properly speaking, produce anything. In The Enigma of Health, rather than introducing Aristotle's intellectual virtue of phronēsis (practical wisdom) as a way of understanding medical practice, Gadamer focuses on how medicine is a technē "with a difference". In this paper, I argue that, despite the richness of his insights, this focus prevents Gadamer from reaching an adequate account of health and the practice of medicine, and I demonstrate how making phronēsis central via a phenomenological description furthers our understanding of the art of healing in important ways. The paper begins with an exploration of Gadamer's understanding of phronēsis and technē (via Heidegger) to provide a foundation for a phenomenological analysis of the art of healing. After considering the shortcomings of Gadamer's analyses, I introduce a working definition of "health" that both captures the spirit of Gadamer's insights and prepares the ground for a phenomenological description. Finally, I introduce concepts from Merleau-Ponty in order to establish an adequate account of the relation between technē and phronēsis and a more nuanced understanding of experience as unfolding within the expressive trajectories forged by bodies that are subject to the weight of the past and the weight of the ideal. The art of medicine, I argue, needs to be understood as expressive behavior in the context of historically and socially situated individuals, institutions, and open trajectories of sense.