The legend of the ancient Macedonian ruler Alexander the Great was infused with new life in the Middle Ages. Medieval literature cast him as a popular subject, a moral exemplum and a model to be emulated by the nobility. One important aspect of this legend was his relationship with women that can be read as a marker of the different representations of the Alexander figure and their cultural contexts. This study examines the Alexander legend as it was reinvented in three major medieval texts, written by the French cleric Gautier de Châtillon, the German writer Johann Hartlieb and the Persian poet Nizami. While Christian literary representations reinvent Alexander as an ascetic, chaste figure, exalting fidelity to one woman, his wife Roxane and alternatively as an ideal of gallantry and courtliness, the Persian romance tradition portrayed him as an energetic, polygamous lover. In each case, his attitude towards women is deployed as a symbol of his political attributes.