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This paper analyzes how the figure of the Virgin Mary came to be adopted as model for rulership and civic pride in the Middle Ages, and how today this can help to identify and articulate what female leadership means. Having dealt with the early medieval definition of Mary as principal intercessor for humankind and Queen of Heaven, I am interested in understanding something of a paradox: How Mary, the paradigm for modesty, became a symbol of political power? In Late Antiquity, Mary was the protector of Constantinople and Rome. Over time she also became the supernatural protector of major Italian city-states, where she came to be identified with the city and its specific cultural-political identity. I propose that my conclusions about the late antique and medieval political significance of Mary can help advance a better understanding of women’s leadership roles, not only in the past, but also in the 21st century. Current politics – as demonstrated by the report of the EU-Foundation Robert Schumann "Europe, Women's Continent” (8 March 2017), by the recent US presidential elections, by the relative vulnerability of female candidates for leadership – reveal that this research can have an impact besides academia in building self-awareness and inspiring public participation on the part of women.