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Among all his pupils Leonardo da Vinci had a long-lasting relationship with Gian Giacomo and Francesco Melzi apprenticed to him as children.
Salaì – “The Devil”
On July 22, 1490, Leonardo was in Oreno looking for the perfect horse for the equestrian monument in honor of Francesco Sforza. There he met the 10-year-old Gian Giacomo Caprotti da Oreno, born in 1480, by chance. The 38-year-old Tuscan genius charmed by the beauty of the boy adopted him. The boy was born in 1480 to Pietro di Giovanni, a tenant of Leonardo’s vineyard near the Porta Vercellina, Milan.
Leonardo nicknamed the boy as Salaì or il Salaìno meaning “The Devil” (lit. “The little unclean one”). Salaì lived up to his nickname. On at least five occasions, Giacomo had run off with Leonardo’s money and valuables. He spent a fortune on apparel, including 24 pairs of footwear. Leonardo had made a list of his recalcitrant ways calling him “a thief, a liar, stubborn, and a glutton”.
Despite Salaì ‘s thievery and dereliction, he remained Leonardo’s servant, and assistant for more than 28 years. Some writers believe that Leonard had a taste for “rough trade” and his relationship with Salaì, his “kept boy”, was anything but typical of a father and a son. Vasari describes Salaì as “a graceful and beautiful youth with curly hair, in which Leonardo greatly delighted.”
In 1563, Gian Paolo Lamazzo in his Libro dei Sogni, included a fictional dialogue between a questioner and Leonardo on “l’amore masculino“.
The questioner asks Leonardo of his relations with Salaì: “Did you play the game from behind which the Florentines love so much?”
Leonardo replies: “And how many times! Keep in mind that he was a beautiful young man, especially at about fifteen.”

Some researchers presume that Salaì was the model for Leonardo’s “St. John the Baptist,“an oil painting on walnut wood. Some consider it to be Leonardo’s final painting between 1513 to 1516.
The piece depicts St. John the Baptist in solitude. St. John dressed in pelts has long curly hair. He smiles in an enigmatic manner, reminiscent of Leonardo’s famous Mona Lisa. He holds a reed cross in his left hand. His right hand points up toward the heaven suggesting the importance of salvation through baptism represented by John the Baptist. Another painter might have added the cross and wool skins at a later date.

Salaì trained as an artist under Leonardo. He became a capable, but not an impressive painter. He created several paintings under the name of Andrea Salaì. His work includes the Monna Vanna, a nude version of the Mona Lisa which might have been based on a lost nude by Leonardo.

Some drawings among the works of Leonardo and his pupils make reference to Salaì’s sexuality. There is a lewd drawing modelled on Leonardo’s painting “St. John the Baptist,” called “The Angel Incarnate.” It depicts a young nude man with an erect phallus. The figure appears to be in the likeness of Salaì. The face of the figure is closer to Salaì’s copy of Leonardo’s painting than to the original John the Baptist in the Louvre. Salaì himself may have drawn them.
Included in a folio of Leonardo, is a page of drawings by a hand other than Leonardo’s. One of them is a crude sketch depicting an anus and identified as “Salaì’s bum,” pursued by a horde of penises on two legs. The page on which this sketch appears is the same page that contains the depiction of a bicycle. None of the drawings on this page is by Leonardo. The page was not seen until a restoration of the volume in the 1960s. Several pages went missing and were later returned. Some suggest that the drawings are by a pupil of Leonardo, perhaps by Salaì.
We might have had more examples of pornographic drawings by Leonardo and his pupils if a 16th century priest had not destroyed the bulk of those erotic sketches.
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Count Francesco Melzi

In 1506, during his second stay in Milan, Leonardo took into his household the 15-year-old Count Francesco Melzi as a pupil. Unlike Salaì, Melzi hailed from a Milanese noble family. Vasari says that Melzi “at the time of Leonardo was a very beautiful and very much loved young man.“
As an adult, Melzi became secretary and main assistant of Leonardo.

As a painter, Melzi worked closely with and for Leonardo. Some paintings attributed to Leonardo during the nineteenth century are today ascribed to Melzi.
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Next → Leonardo da Vinci: Part 5 – His Final Years
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