How does prayer shape action? How does sustained engagement in deep prayer shape our very freedom to act? This volume explores the relationship between Christian contemplative prayer and the exercise of freedom. Over the past half century, the desire for a better integration of spirituality and theology has emerged as a significant theme in theological writing. While the question of freedom has not been absent from this discourse, this volume highlights it by bringing it to the very center of the conversation. Eleven theologians explore the dialectical relationship between contemplation and freedom by engaging with a wide array of sources ranging from Maximus the Confessor to Edith Stein, from Howard Thurman to Bernard Lonergan, from the Tibhirine martyrs to M. Shawn Copeland. This symphony of voices unveils the methodological fruitfulness of placing contemplative prayer at the center of life, theory, and practice.