The Baptistery and the Collegiata (collegiate church) in Castiglione Olona were commissioned by Cardinal Branda Castiglione (1350-1443) from the family of the feudal lords of Castiglione. The collegiate church and its attendant structures, among them the baptistery, were erected between 1422 and 1425, and they occupy the site of an earlier citadel. The baptistery is said to have been built on the foundations of one of the citadel's towers.
The cardinal commissioned the frescoes in Castiglione Olona from Masolino after completing the frescoes in San Clemente, his titular church in Rome. The painting program is dedicated to John the Baptist, as appropriate for a baptistery.
The fresco cycle begins to the left of the door with the Annunciation to Zacharias. It then continues to the right of the door with the Visitation (largely destroyed). The frescoes on the north wall are the Birth of the Baptist (lost) and Zacharias Naming the Infant John (in very poor condition). The cycle continues in the altar room and it is concluded on the south wall with the Feast of Herod, Salome Bringing the Head of the Baptist to Herodias, and the Burial of the Baptist. The alter room contains the most important scenes of the cycle, John the Baptists's Sermon in the Wilderness and Sermon at the Jordan, the Baptism of Christ, Herod and Herodias, John the Baptist in Prison.
The images of the four evangelists with their respective symbols in the radiating compartments of the vaulting complement the iconographic program presented on the walls below.
The paintings in the Baptistery are unanimously attributed to Masolino by scholars. Because of the poor condition of the frescoes on the north and west walls, it is no longer possible to determine to what degree, if any, Masolino relied on assistants in the execution of the cycle.
The paintings in the choir of the Collegiata celebrate the triple patronage of the building: the church was consecrated to the Virgin and to the cardinal's own name-day saints, the archdeacons Stephen and Lawrence. The vault frescoes, depicting scenes from the life of the Virgin, were executed by Masolino at about the same time as those in the baptistery, c. 1435. On the walls below, a cycle with scenes from the lives of the archdeacons Stephen and Lawrence was painted by Il Vecchietta and Paolo Schiavo somewhat later.
The six scenes from the life of the Virgin fill the six compartments of the cross-ribbed vaulting of the polygonal presbytery, their unusual arrangement dictated in part by the relative sizes of the available spaces.
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