Leonardo did complete this very small painting but the original has probably been lost. Several copies still exist and there is strong speculation that two of these are from the hand of Leonardo himself, but this is still the subject of some debate and they could just have easily come from talented pupils. The original work can be securely dated at 1501 as a letter from April of that year mentions Leonardo is working on Madonna of the Yarnwinder.
One of the most interesting and complete sketches Leonardo ever did was for this painting; a close look shows this work was based around the geometric figures of triangles and ellipses. An excellent red chalk drawing of the Madonna's head and shoulders also exists in the Royal Collection at Windsor Castle.
This work, intended for Florimond Robertet, Secretary to the King of France, shows the winder as shaped like a cross; this symbolizes the Passion of Christ and His future death. It appears that Mary wants to pull the Child away from the symbol of His future, but even she is powerless to prevent the Crucifixion which is part of His destiny. Of the two works, one is very green whilst the other is quite blue; the landscapes also differ significantly with one showing a vicious mountain range beneath a vivid blue sky while the other runs down to the sea.
Leonardo prepared for paintings that included the Christ child or the infant St. John the Baptist by drawing dozens of studies of little children. Most of his children appear between nine and eighteen months, all are shown nude and all look similar enough to make the viewer wonder whether the one child modeled for each painting.
This painting is sometimes called Madonna of the Spindle or the Madonna with the Distaff.