The Astonishing Stories of Saints & Sinners in Old Master Paintings

Three women saints in rich fabrics, holding their symbols.
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“God, make me good, but not yet,” Saint Augustine wrote in his 3rd-century autobiography Confessions, forever immortalizing the at-times-contradictory human struggle between good and evil. Indeed, the dramas of saints and sinners are at the heart of the Western art historical canon. Adorning churches, homes and civic spaces, these artworks served to be didactic, devotional, forewarning and entertaining. Sotheby’s Old Masters Online auction (January 21–February 5) presents a trove of images of both the pious and damned. Click ahead to learn their stories. — Kathleen White

The Astonishing Stories of Saints & Sinners in Old Master Paintings

  • Circle Of Cornelis Cornelisz van Haarlem, The Prodigal Son. Estimate $12,000–18,000.
    The Parable of The Prodigal Son tells the story of a young man who squanders through his inheritance with wild abandon. Having fallen upon hard times, he penitently returns home to his father, who, overcome with joy, forgives him and celebrates him with a feast. Ultimately a story about the nature of forgiveness, this painting presents the hedonistic escapades before his reformation.

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  • Follower of Francisco de Zurbarán, Saints Agatha, Lucy and Apollonia . Estimate $6,000–8,000.
    This sumptuous paintings shows three saints, Agatha, Lucy and Apollonia, clad in rich fabrics, holding symbols or instruments related to their martyrdom. Together known as the Virgin Martyrs, the three women were born to wealthy families, and each consecrated her virginity to God. Upon the refusal to marry, they were tortured and killed.

    Saint Agatha is shown holding a tray with two breasts, as hers were severed during her torture and execution. Saint Lucy presents a silver platter with two eyes – narratives of her death included stories of eye-gouging. Saint Apollonia is shown with pincers – her teeth were pulled out in her martyrdom. Today, Saint Apollonia is the patron saint of dentists.

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  • José Cortez De Alcocer, Saint Joseph and Child. Estimate 30,000–50,000.
    Saint Joseph was the husband of Mary and the foster father of Jesus. A modest carpenter, St. Joseph is nevertheless a descendant from the lineage of Old Testament hero David, of the story of David and Goliath. Though usually depicted humbly, here St. Joseph is shown holding a radiant Christ child, and wearing a lustrous lilac-gray tunic and lavish gold crown.

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  • Jacob De Backer, The Annunciation; Pentecost. Estimate $10,000–15,000.
    These two scenes present important moments in the New Testament. In the Annunciation panel on the left, the Virgin Mary is visited by the Angel Gabriel and told she will become the mother of God. In the Bible, the Virgin Mary is the only person born free from original sin.

    On the right is a scene of the Pentecost, when, after Jesus’s resurrection and Ascension into heaven, the Holy Spirit visits his disciples and inspires them to share Christ’s message.

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  • Artus Wolffort, Esther in the Women's House of Ahasuerus. Estimate $15,000–20,000.
    The Old Testament queen Esther is considered one of the great heroines of the Judeo-Christian tradition. A Jewish orphan of great beauty, she married King Ahasuerus of Persia, a temperamental man. Esther becomes aware of a plot to kill all the Jews in Persia, devised by a man named Haman. She orchestrates a dinner with the King and Haman, and with subtly and cunning reveals both her Jewish origins and Haman’s plot. The King, beguiled by Esther, is sent into a fury and executes Haman. Scenes of Esther were depicted with some frequency during the Renaissance, when her story was viewed through a humanist lens of intellectual triumph over adversity.

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  • Jacopo Paolo Marieschi, Saint John The Merciful Distributing Alms, A Bozzetto. Estimate $7,000–9,000.
    Saint John the Merciful was the Patriarch of Alexandria in the 7th century and was known for his boundless generosity. As a young man, he was said to have seen a vision Compassion, appearing as beautiful woman wearing a crown of olives. In this painting, Saint John is shown distributing money to the poor, whom he called his “Lords and Masters,” referring to the Christian belief that in the kingdom of heaven "the last will become first."

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  • Antonio Arellano, The Conversion of Saint Paul. Estimate $10,000–15,000.
    Saint Paul was a soldier called Saul who fought with zeal against the spread of Christianity, and was renowned for his persecution of Christians. But, in the one decisive moment shown here, he experiences a change of faith and is converted. While on the road to Damascus, he was flung from his horse. A blinding light shown upon him and he heard the voice of Jesus speaking to him. Paul remained blind for three days after the vision, mirroring the three days before Christ's resurrection. After the experience, Paul became an important Christian proselytizer and writer.

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  • Michelangelo Ricciolini, Daniel In The Lion's Den. Estimate $20,000–30,000.
    Daniel was a devout Babylonian leader whose rivals enacted a law to forbid prayer. When he was found praying to the God of Israel, he was cast into a lion’s den. God tames the lions, and the next day the King frees Daniel. This Baroque depiction of the scene has a nearly theatrical quality showing Daniel in a green garment beside the now almost endearing lions sent to devour him.

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