The fountain mural discovered in 2000 in the Tuscan town of Massa Marittima has drawn international attention due to its rare iconographic allusions to fertility and witchcraft in late thirteenth century Italy. The mural, which depicts eight women underneath a deciduous tree with phalli hanging from its branches in lieu of fruit, raises numerous questions. In this thesis, I examine the positive classical iconographic associations to fertility and auspiciousness and how these symbols came to be reinterpreted within a Christian context as elements of sin and temptation. Furthermore, the connections between the lingering classical prototype of a woman as a being of unbridled sexuality, temptation, and bearer of prophetic knowledge continued to manifest themselves in medieval folklore beliefs of witchcraft and its artistic representations in the high and late Middle Ages. The mural is evidence of how these anxieties were effectively appropriated into the genre of propagandistic political art during a time of civil unrest in central Italy.