Gregory the Great depicts himself as a contemplative who, as bishop of Rome, was compelled to become an administrator and pastor. His theological response to this existential tension illuminates the vexed questions of his relationships to predecessors and of his legacy. Gregory develops Augustine’s thought in such a way as to satisfy John Cassian’s position that contemplative vision is grounded in the soul’s likeness to the unity of Father and Son. For Augustine, “mercy” lovingly lifts the neighbor toward life in God. Imitating God’s own love for humankind, this mercy likens the Christian to God’s essential goodness and, by this likeness, prepares him or her for the vision of God, which Augustine expects not now but only in the next life. For Augustine, the exercise of mercy can—when useful—involve a shared affection or understanding. Gregory makes this shared affection essential to the neighborly love that he calls “compassion.” In this affective fellowship, Gregory finds a human translation of the passionless unity of Father and Son—so that, for Gregory, compassion becomes the immediate basis for and consequence of seeing God—even in this life. Compassion does not degrade; rather, it retrenches the perfection of contemplation. Reconciling compassionate activity and contemplative vision, this creative renegotiation of Augustine and Cassian both answered Gregory’s own aspirations and gave to the tumultuous post-Imperial West a needed account of worldly affairs as spiritual affairs.