Baldassare Castiglione owned a Madonna by Raphael and it is probable that he inherited it from Cardinal Bibbiena. If it came from another source, then Castiglione would have owned two Madonnas by Raphael. It is possible that the Leeswood Tondo is a Madonna owned by Castiglione.
If the Bibbiena Madonna was a portrait, then it might be argued that it was a betrothal portrait of Maria Bibbiena, the Cardinal's niece and fiance of Raphael. The letter from Raphael to his uncle, dated 1 July 1514, would suggest that the earliest date for a betrothal portrait would be summer 1514.
As it is likely that the Sistine Madonna was a funerary decoration for Julius II, produced c.1511, then this would disqualify the Tondo from being a betrothal portrait of Maria Bibbiena.
The discovery of the word "Felic..." on the reverse of the Tondo has lead to the supposition that this was the name of the model for the Madonna. Raphael was a member of the inner circle of both the court of Urbino and the court of Julius II : also within these groups was Felice della Rovere, daughter of Julius II and niece of the Duchess of Urbino. Felice had a son, who in 1511 would have been three or four years old.
It is suggested that they were the models for the Tondo, and that the Tondo was produced as an exemplar for Raphael's workshop to follow in the painting of the Sistine Madonna. It is likely that Raphael himself painted the heads of St.Sixtus and St.Barbara, and that the models for the these were Julius II and Eleonora, wife of Francesco Maria della Rovere, Duke of Urbino, nephew of Julius II. In 1511 Felice would have been about 17 to 18 years old, Eleonora 18, and Julius 68.
An immediate precedent for a "family" Madonna is mentioned by Vasari in his life of Pinturicchio429:
"Over the door of one of the rooms of the same palace(the Vatican) Pinturicchio portrayed the Signora Giulia Farnese in the face of a Madonna; and in the same picture is a figure in adoration of the Virgin, the head of which is a portrait of Pope Alexander."
Giulia Farnese was the mistress of the Borgia Pope, Alexander VI, who was responsible for exile of Cardinal Giuliano della Rovere, later Julius II.
After the death of Julius II in 1513, when the collection was dispersed, it would be natural for the monks of San Sisto to acquire the Sistine Madonna, because of their long-standing relationship with Julius II. It was Julius, when a Cardinal, who signed the permissions in 1499 for the monks to rebuild their church, which was finished in 1511 and reconsecrated in 1514. The monks were also probably influential in the decision by the town of Piacenza to join the Papal States in 1512, which considerably strengthened Julius's position in his war with the French in Northern Italy. It may be that Julius bequethed the Sistine Madonna to the monks of San Sisto; and had the little tower added, behind the female saint, to signify that she was actually St.Barbara, whose remains rested in San Sisto
Julius may have also owned the exemplar, which may have passed to Cardinal Bibbiena, the treasurer to the in-coming Pope Leo X. However it is known that Castiglione was a very close friend of Felice, and it may be that he acquired the Tondo because of, what Cartwright calls, his "hopeless passion for some exalted object"357; a suitable description of Felice, being the Pope's daughter, and married to a senior member of the Orsini family. Castiglione records this "hopeless passion" in the two sonnets discovered, thirty-one years after his death, behind a mirror by his daughter-in-law, along with a portrait of a beautiful and illustrious lady by Raphael.430
Raphael painted Castiglione's portrait, which now hangs in the Louvre, in 1515. Castiglione went to Spain in 1524, and took this portrait, and possibly other favourite works, with him. The fate of his own portrait may provide insights into the possible fate of other works in his collection. The portrait was returned to Mantua after his death, and it is mentioned in 1606 as being in the collection of his son.431
The 1903 Musee du Louvre catalogue states that:
"After the death of Castiglione, it belonged in turns to the duke of Mantua, Charles I, a Dutch amateur named van Asselen, at whose house it was copied by Rubens and Rembrandt, and to Mazarin, whose heirs sold it to Louis XIV. It was estimated then 3,000 francs..."432
Cartwright suggests that van Asselin (or, Lucas Van Uffelen, a friend of Van Dyck) bought it direct from Mantua.
However recent research, published by Sylvie Béguin433, in 1983, has discovered a letter from Camillo Castiglione, son of Baldassare, to Giulio Veterani, minister to the Duke of Urbino, dated August 1588. In the letter Castiglione offers the portrait of his father to the Duke. A 1623-4 inventory of the Palace of Urbino mentions a portrait of Castiglione without mentioning the artist.
The Duke of Urbino died on 28 April 1631. Part of the estate went to Vittoria della Rovere, and by her marriage to Ferdinand II, Grand Duke of Tuscany, it passed into the Medici Collection now housed in the Uffizi in Florence. The other parts were sold in Urbino and Castel Durante, Urbania. The Castiglione portrait was bought by Van Uffelen and taken to Amsterdam. Shearman434 supposes that the portrait was part of the van Uffelen collection, which was bought by the
"Spanish-Jewish jewel-and-armaments dealer doing business in Paris, Antonio Lopez, who later(1641) sold the Raphael to Cardinal Mazarin."435
Camillo Castiglione's stated reason for offering his father's portrait to the Duke of Urbino was that:
"The soul of the Count, if it could learn of this, would draw great consolation from knowing that the picture will be conserved in this court where the Count spent a great part of his life and under the protection of a Prince, who is descended from those glorious Princes, whom he served for so long."436
If the Tondo
has a strong della Rovere family connection, through Felice della Rovere, and if it was in Castiglione's collection, then it is very possible that this painting was also offered to the Duke of Urbino, at this time.
It is also possible that, through the Gonzaga family connection, part of the Castiglione Collection passed to the Duke of Mantua, and from there to London. Most of the Mantuan collection did find its way to England, especially into Charles I's collection, and no doubt into the collection of other English connoisseurs, through the double-dealing of the agent in Italy, Daniel Nys437. However Castiglione's portrait does not appear in the Royal inventories, although there are numerous Madonnas listed including the interesting Madonna with St.Katherine.
Selwyn Brinton438 cited (1927) Dr.Alessandro Luzio, head of Mantuan Archives:
"Though the 'great Mantuan collection' has thus disappeared into space, who knows - as Dr.Luzio has suggested - what treasures may yet be preserved unrecognised in the older private collections, the "castelli signorili" of England?"
It may well be that Castiglione's Madonna followed his portrait from the collection of his grandson into the Mantuan collection and from thence to Whitehall, Somerset House or one of the "castelli signorili".
||Vasari, G. : Lives : ed. Foster : vol. III, p.289
||Cartwright, J. :The Perfect Courtier : vol.I, p.93
||ibid. : vol.II, pp.449-450
||Lafenestre, G. & Richtenberger, E. The Louvre : Maison Quantin : 1903 (?) : p.99
||Chastel, A. et al : Raphael dans les Collections Française p.86
||ibid. : p.86
||Alsop. J. : The Rare Art Traditions : p.456
||Chastel, A. et al : Raphael dans les Collections Française p.86
||Alsop. J. : The Rare Art Traditions : p.148-151
||Brinton, S. : Gonzaga Lords of Mantua : Methuen : 1927 : p.217, note 1