Giovanni Ambrogio de Predis, 'An Angel in Red with a Lute', about 1495-9

In April 1483 Leonardo da Vinci and two Milanese painters, half-brothers Ambrogio and Evangelista de Predis, signed a contract to gild and paint a large, wooden, sculpted altarpiece recently completed by the Milanese sculptor Giacomo del Maiano. A new religious group, a confraternity formed for the devotion of the Immaculate Conception, commissioned the altarpiece; it would be the main focus of worship in their newly built chapel in the Church of San Francesco Grande, Milan.

The artists were commissioned to provide three paintings which would be placed within the structure of the altarpiece. These were of the Virgin and Child with angels, and two pictures showing angels making music. Leonardo tackled the Virgin and Child – the central image, now known as ‘The Virgin of the Rocks’. Ambrogio de Predis almost certainly painted the angel playing a lute, and when Evangelista died he appears to have enlisted his friend, Francesco Napoletano, to paint the angel in green playing a vielle.

The sculpted parts of the altarpiece are now lost, so we don‘t know exactly how it looked – but a list attached to the contract gives us an idea of the sculptures, and the impression of a complex and elaborate structure. The main sculpture was of the Virgin Mary. She wore a necklace of gold, pearls and enamel, suggesting that she was very lifelike, and stood beneath a domed canopy. The angels playing musical instruments might have stood on either side of this statue. Leonardo’s painting was the main image and was placed below the sculpture. The list also mentions carved narrative scenes ’of Our Lady', perhaps scenes from Mary’s life. At the base of the altarpiece was another carving, possibly Christ as a baby in his crib.

Leonardo’s picture in the National Gallery was painted to replace an earlier version that he had made for the altarpiece (the first is now in the Louvre, Paris). The composition of the Paris version is almost identical – the only difference is the angel, who in the Paris version looks out at us and points towards Saint John the Baptist, interrupting the connection between the Virgin and Christ.

It is not clear why two versions were made. Surviving documents that date to the early 1490s tell us that Leonardo and Ambrogio de Predis were in dispute with the confraternity about payment for their pictures; they were asking for more money than originally agreed because the materials had turned out to be more expensive than estimated. There is no evidence to prove what happened next but it seems that Leonardo sold his picture elsewhere, having been unable to persuade the confraternity to pay him the extra required.

The style of our version suggests that it was begun in the early 1490s, shortly after the dispute began. When the French captured Milan in 1499, Leonardo left the city for Florence without finishing the picture. In 1506 the confraternity demanded Leonardo return to Milan to complete it within two years. He was finally paid in 1508. The confraternity’s chapel was destroyed in 1576, the altarpiece was broken up and parts were sold.