The transept holds works dating to the most diverse periods, bearing witness to the history of the building and the Order of the Servants of Mary. At the end of the left transept has stood since 1708 the panel of Our Lady of Mercy painted in 1436 by Giovanni di Paolo for another chapel in the church. The Virgin Mary, here celebrated as the Queen of Mercy, is wearing sumptuous robes and a crown on her head of gold lilies that recall the heraldic emblem of the Servites. Mary covers two group of faithful with her cloak; on the left are women, among whom can be identified Saint Giuliana Falconieri; on the right are the men, with Saint Philip Benizi in the forefront. The two saints, members of the Order of the Servants of Mary, are presented as exemplary figures of devotion to Our Lady. The meaning of the open cloak is an ancient tradition and refers to the legitimacy of children kept under the cloak of marriage and also to the custom that anyone who takes refuge under the sovereign’s cloak has a right to grace. This type of image is very widespread and always timely because it indicates the Blessed Mother’s mercy towards the Christian people.
In the altar under this painting are the moral remains of Blessed Gioacchino Piccolomini (1258-1305), a member of the Order of the Servants of Mary who was particularly attentive to the suffering of others and is venerated today as protector of the newborn. A miraculous episode in which he figures is illustrated in a canvas painted in 1633 by the Sienese painter Rutilio Manetti, placed on the left wall of the chapel. Struck by an epileptic attack during Mass, he fell to the ground, while the wax candle he was holding remained miraculously upright.
On the opposite wall is a painting of the city of Siena struck by the plague, made by Astolfo Petrazzi right after the epidemic of 1630-31. In the foreground two saints, looking upwards, implore healing for the sick of Siena shown behind them; in the background, the city of Siena is easily recognizable. Above, the dove of the Holy Spirit, surrounded by a garland of angels, hovers above a frame which at one time contained the image of the Madonna of the People by Lippo Memmi, now on temporary deposit at the Pinacoteca Nazionale.
The first apse chapel on the left, now dedicated to The Nativity, represented on a panel painting by Taddeo di Bartolo, was originally entitled to Saints John the Baptist and John the Evangelist, as testified by the fourteenth-century frescoes discovered again in the nineteenth century. The wall paintings, by artists in the workshop of Pietro Lorenzetti, illustrate: on the right The Beheading of Saint John the Baptist and Herod’s Banquet; on the left, The Ascension of Saint John the Evangelist, welcomed into heaven by Jesus and the Apostles.
The next chapel on the right is dedicated since the eighteenth century to Our Lady of Sorrows, who is represented by a papier maché statue made in 1836. This iconography recalls Simeone’s prophecy to Mary when Jesus was being presented in the temple: “And a sword will pierce your own heart” (Luke 2:35). The emblem of Mary with her heart pierced by seven swords is promoted especially by the congregation of the Seven Holy Founders of the Servants of Mary and refers to the tradition of the “Seven Sorrows” she would have to bear.
We now come to the high altar on which, over the centuries, various sacred images have been placed, starting with Coppo di Marcovaldo’s Bordone Madonna and coming up to the current arrangement with the altarpiece of The Coronation of the Virgin painted in 1500 by Bernardino Fungai.
Looking up above the altar, we can admire the stained glass windows installed during the nineteenth-century restorations, designed by Alessandro Franchi and Giuseppe Catani. The central window represents the Immaculate Conception, the title of the church.