The special bond between the Order of the Servants of Mary and the Blessed Virgin is evident in the presence in the church of numerous paintings depicting episodes in the life of the Mother of God. We can follow the chronology of her life in the paintings, starting from the canvas showing The Birth of the Virgin, placed in the second chapel on the right and painted by the Sienese artist Rutilio Manetti on a commission from Calidonia Bindi. In the foreground are the nurses holding a basin in which they will bathe the newborn Mary, shown in her mother Anna’s arms. In the middle ground and the background, the light brings out the different expressions of the characters as they react to the event: two women dressed in black inform the pensive Joachim of his daughter’s birth, while a servant girl runs into the kitchen to tell the other servants what has happened.
Mary lived a simple childhood, without sensational episodes, until her early youth was marked by an event that would change her life and the course of history forever: the announcement of the coming birth of Christ, portrayed in the late sixteenth century by Francesco Vanni in a painting commissioned by the Cancelli family, placed in the first chapel on the left. The young girl, intent on her reading, receives the visit of the Archangel Gabriel who tells her that soon she will conceive and bear a son, and that his name will be Jesus. In the sky, the figure of God the Father emerges from a division in the clouds. The clothing of the figures reflects the lively, iridescent colors typical of Vanni. The artist paints the same subject in two other pictures in the transept on either side of the triumphal arch: on the left is the Annunciation Angel and on the right the Virgin Annunciate.
The prophecy comes true and Mary gives birth to Jesus in a stable in Bethlehem. The angels announce the event to shepherds in the surrounding fields, and they run to worship the Messiah. The Adoration of the Shepherds is shown in the central panel of a triptych painted in 1404 by Taddeo di Bartolo and located in the first transept chapel on the left. In the center, in a manger, lies the Baby Jesus illuminated by light streaming from the dove of the Holy Spirit. Our Lady presents her Son to the two shepherds kneeling in prayer. On the rock on the left a goldfinch, with its red head, alludes to the Passion which the Baby will have to undergo for the salvation of mankind. The event appears also in a canvas painted by Alessandro Casolani at the end of the sixteenth century which is on the left wall of the chapel dedicated to Saint Philip Benizi.
Subsequently, the Holy Family received a visit from the three Magi, as depicted by Dionisio Montorselli in the 1680s for the church of Fontegiusta and later placed in the chapel dedicated to the dead Christ, represented in a polychrome terracotta sculpture under the altar. The three Magi pay homage to the Child, illuminated by the light from a comet, and offer him gold, incense, and myrrh, which symbolize, respectively, Christ’s temporal power, divine nature, and human mortality.
Returning to Nazareth, Mary cares for her son until he begins preaching at the age of 30. Later she is by his side in his dramatic suffering during the Passion, and lives, together with the Apostles, the extraordinary moments of the Resurrection up to the Pentecost, when the Holy Spirit descended on them. The disciples accompany Mary up to her dormition, after which she is taken body and soul into Paradise. There she is crowned by Jesus, who thus makes her a participant in his royalty, becoming Queen of Heaven and earth, as we remember now in the fifth Glorious Mystery of the Rosary. The Coronation, a frequent subject in Sienese painting, is celebrated in the altarpiece made by Bernardino Fungai in 1500, on the church’s high altar. In the center, two angels hold in one hand an olive branch, a symbol of the peace brought by Christ and the personal emblem of Mary, and in the other the edges of a precious gold cloth, a symbol of divine light. Seated in front of this cloth of honor, which stands out against the blue sky, are Mary and Jesus, richly dressed; between the Mother and Son appears the dove of the Holy Spirit. The two main characters are flanked by hosts of angel musicians and saints. Among the saints can be identified Saint Clement the Pope, the first on the left in the second row, Blessed Giovacchino Piccolomini in the foreground on the far left, and Blessed Francesco Patrizi on the far right. The painting calls to mind other works in Siena devoted to the Virgin Mary like the extraordinary Maestà by Duccio, which Fungai had certainly seen because it stood on the high altar of Siena Cathedral from 1311 to 1506. Furthermore, the composition of Fungai’s altarpiece is very similar to the one of The Coronation of the Virgin painted in 1483 by Piero del Pollaiolo for the church of Sant’Agostino in San Gimignano.