“Excellent Lord: —Knowing your Excellency's love for painting and your passion for protecting it as shown in the patronage of Ginlio Eomano; —being further desirous of pleasing your Excellency, —I have taken the opportunity of Messer Pietro Aretino's arrival [in Venice] to paint his likeness, and as he comes — a second St. Paul —to preach the virtues of your Excellency, and I likewise know that you are fond of so faithful a servant because of his many virtues, I make you herewith a present of his portrait. But I also bear in remembrance the Signor Girolamo Adorno who adored the Marquis of Mantua, and as he was a qualified gentleman, I send your Excellency a present of him also. These may not be gifts worthy of so great a person as your Excellency.... Most devoted servant, Titiano Vecellio.”

—  Titian

Quote from a letter of Titian, to the Marquess Gonzaga of Mantua, from Venice 22 Juin 1527; as quoted by J.A.Y. Crowe & G.B. Cavalcaselle in Titian his life and times - With some account..., publisher John Murray, London, 1877, p. 317
Assuredly Titian at this time had Messer Pietro Aretino for a sitter; this letter proves his intimacy with the secretary of Giovanni de Medici
1510-1540

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Italian painter 1488–1576

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“Illustrious Lord, hearing that your Excellency has gone to the court of his Imperial Majesty [Charles V], I abstain from coming to Mantua, sighing at my bad fortune in not having left Bologna soon enough to meet your Grace. At Venice I shall prepare the copy of the portrait of his Majesty, which I take home with me at your Excellency's bidding.”

Titian (1488–1576) Italian painter

In a letter to the Duke of Mantua, from Bologna, 10 March 1533; as quoted by J.A.Y. Crowe & G.B. Cavalcaselle in Titian his life and times - With some account..., publisher John Murray, London, 1877, p. 370
The portrait which Titian took home and repeated a second time he doubtless sent to Charles V. The replica was not sent to Mantua till after 1536, but there it appears to have remained. Another example besides that of the Madrid Museum came into the hands of Charles the First of England.
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Source: https://commons.wikimedia.org/wiki/Titian#/media/File:Tizian_081.jpg
Source: https://commons.wikimedia.org/wiki/Titian#/media/File:Tizian_081.jpg

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