Gregory the Great was, after Augustine of Hippo, perhaps the most influential of the Fathers in the Latin West during the Middle Ages. He put Augustine’s thought into a form which proved accessible and acceptable to mediaeval readers, and he added much of his own, notably in his preaching, in which he interpreted the Bible with equal emphasis on the practical living of a good Christian life and the aspiration of the soul towards God and the life to come. This study looks at Gregory’s thought as a whole and tries to show what was most important to him and the way he arrived at a balance between the active and the contemplative, the ‘outward’ and the ‘inward’ in his own mind. There is a tailpiece on the influence of his ideas in later centuries.