During the Middle Ages, legends of Mary were widespread and influential, and were treasured for their spiritual significance and teaching value. These ancient legends also helped inform the piety of the day, shaping people's liturgical and private devotional practices.

The Legend of Theophilus

One of the most popular legends from the Middle Ages involved a sixth-century archbishop named Theophilus who lived in what is now Turkey. He was a humble man who served as archdeacon for the Archbishop of Celia. When he was unanimously elected to serve as bishop, he turned down the post because of his humility.

Later, however, when Theophilus was forced to step down as archdeacon for no clear reason, he was so filled with rage that he turned to the devil. The devil encouraged him to sign a pact in which he would renounce God and the Virgin Mary in exchange for the position as bishop. Theophilus signed the pact with his own blood.

He became bishop, but his conscience troubled him. After he fasted for forty days, the Virgin Mary appeared to him and chastised him for what he had done. After he repented, she agreed to intercede before God on his behalf. Later, she appeared to him in a dream and tore up the pact. He awoke surrounded by scraps of parchment. He made a confession to his bishop and died in peace.

This legend offers a glimpse into the medieval perspective of the Virgin Mary. During the Middle Ages, she was increasingly viewed as the woman who had the power to cancel the works of the devil, to make right even lives that had gone horribly awry.

Increasingly, Mary was viewed as this type of mediating (some might even say meddling) mother who makes things right for her children. Despite her exceptional example of piety and purity, she was not generally viewed as a figure of judgment but of mercy and reconciliation. Christ, on the other hand, was most often portrayed as a stern judge. According to Sally Cunneen, in her book In Search of Mary, many of the surviving medieval images of Christ show him as the stern Shepherd who separates the sheep from the goats. It was during the middle ages especially that Mary came to be associated with mercy while Christ came to be associated with judgment.

Images of Mary generally shifted during the Middle Ages as well. The early art from this period often emphasized Mary's greatness, while the art produced later emphasized her tenderness. As she came to be seen as increasingly tender and accessible, prayers to her for intercessions increased as well. Some people even prayed to Mary instead of Jesus.

The influential writer Bernard of Clairvaux expressed this progression away from the son and toward the mother this way, “If you fear the Father, go to the Son; if you fear the Son, go to the Mother.”

The Golden Legend

Another influential text that developed during the Middle Ages was called The Golden Legend. This collection of stories of the lives of the saints was most likely compiled around 1290 by Jacobus de Voragine.

The Golden Legend was much loved for the way it both humanized and spiritualized the lives of holy people. For example, it drew from a variety of ancient and apocryphal texts to fill in many biographical details about Jesus and Mary which had not been supplied by Scripture.

The Golden Legend was something like a medieval encyclopedia of the saints, containing stories of varying pedigree. These stories were valued for the way they offered spiritual lessons to the faithful, but were not always accepted uncritically. Some of the details supplied in these accounts were more fanciful than historical, more symbolic than miraculous.