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Stephen Harding was a monk of Sherborne Abbey, Dorset, who became the influential third Abbot of Cîteaux, a mentor to Bernard of Clairvaux and wrote the constitution of the Cistercians. In this chapter, I consider his portraits, his life (drawing on modern biographers as well as on William of Malmesbury and on Conrad’s Exordium Magnum Cisterciense) and his writings. His spirituality, administrative skills, planting of monasteries and sharing with Jews in the study of the Scriptures were extraordinary.