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Agnolo Bronzino, Portrait of a Young Man with a Book, oil on poplar panel.
Michelangelo Merisi da Caravaggio, Boy Peeling a Fruit, oil on canvas
Canaletto, The Piazzetta: Looking East, with the Ducal Palace.
Canaletto, The Piazza San Marco: the Northeast Corner.
Thuringian School, The Passion of Christ: The Arrest; The Flagellation; Christ on the road to Calvary; The Crucifixion; The Descent; The Entombment; The Descent into Limbo, ca. 1400
Lucas Cranach I, Cardinal Albrecht von Brandenburg as Saint Jerome in a Landscape
Circle of Dieric Bouts, The Virgin and Child before a gold brocaded cloth of honor
Pieter Coecke van Aelst I, Saint Jerome in his study
Balthasar van der Ast, Grapes and other fruit in a basket, cherries and a peach on a Delft plate, tulips, irises and other flowers in a Wan-li vase, shells, and other fruit on a stone table, with parrots
Hubert Robert, The Canal, 1774.
Guido Reni, The Martyrdom of Saint Apollonia

Possibly Caravaggio’s first canvas and a rare early work by Agnolo Bronzino are poised to far exceed the artists’ auction records this week at Christie’s New York in its Old Master paintings and Renaissance sales.

Bearing a price tag of up to $5 million, Boy Peeling a Fruit (ca. 1592) could blow away Caravaggio‘s auction record of $145,000, set at Sotheby’s New York in 1998. The seller is identified only as a European collector. (Keep in mind that this doesn’t reflect the private market, which is often known to be wildly divergent from public performance, and that a Caravaggio was recently valued at $15.8 million (see Sotheby’s Wins Case Over $15.8 Million Caravaggio).

Featuring works by Canaletto, Hubert Robert, Theodoor Rombouts and Guido Reni, the Wednesday morning sale is estimated to bring up to $39 million with 56 works on offer. The same sale last year brought just $15.8 million. If the sale reaches its high estimate it will match the house’s 2010 total, which was its largest January Old Master auction in 15 years.

The sale also includes examples by Northern masters like Balthasar van der Ast and Pieter Brueghel, England’s Sir Joshua Reynolds and the Swiss-born Henry Fuseli. Also estimated to go for up to $5 million is a pair of 16-inch-wide canvases by Canaletto: The Piazza San Marco: the Northeast Corner and The Piazzetta: Looking East, with the Ducal Palace. The latter represents one of architecture’s most recognizable facades, bathed in late-afternoon sunlight.

Tagged at $8–$12 million is Bronzino’s Portrait of a Young Man with a Book, which Christie’s is bringing to market for the second time in its Renaissance sale Wednesday afternoon (see The Old Masters Market Is Restoring Its Image to Make It Sexy). The three-foot-high oil on panel failed to sell in 2013, when it was estimated at $12-$18 million. The sale catalogue indicates that Christie’s owns the work, in part or in full, though it says that “a private collector” is offering it for sale. An essay by Bronzino scholar Carlo Falciani dates the painting to between 1525 and 1527.

If it finds a buyer, the Bronzino will smash the auction record for a work by the Florentine, which is $71,049, achieved at Paris auctioneer Marc-Arthur Kohn in 1998. (A work described as being by an artist in Bronzino’s circle, meanwhile, achieved $255,335 at Bukowski’s Stockholm in 2009.)

The Renaissance sale, Wednesday afternoon, is expected to total as much as $27 million with 55 lots, considerably shy of the $44.9 million total for the same sale last year. The next-highest estimate after Bronzino is $1.2–$1.8 million for a Thuringian School–style panel painting from ca. 1400 that shows the Passion of Christ and other biblical scenes. A panel by Lucas Cranach portraying a cardinal as Saint Jerome carries a high estimate of $1.5 million. A thriftier bidder could take home a ca. 1455 page from an illuminated manuscript that depicts Saint Luke painting the Virgin for just $7,000.

But the main attraction is the rare early paintings by great masters.

Several dealers surveyed by artnet News indicated that while the works seem to be genuine, they are not the trademark examples that trophy hunters generally desire—they lack the high drama of Caravaggio’s biblical scenes or the hard-edge style of later Bronzinos such as the Frick Collection’s portrait of Lodovico Capponi. The estimates are reasonable, though, they said, considering such paintings’ extreme rarity. All confirmed the presence of new potential buyers in China and Russia, not historically serious collectors of Old Masters. The question is whether these buyers will be sufficiently entranced by a brand name to invest in such early works.

The Caravaggio canvas was created when the artist was 22 and boarding with Monsignor Pandolfo Pucci da Recanati, whom he mocked as “Monsignor Salad” for serving meals consisting only of lettuce, according to an early biography. No less a figure than English painter Joshua Reynolds snatched the painting up at Christie’s London in 1795, at which time it was thought to be by Murillo (Bartolomé Esteban, not Oscar—see Instagrammers Step on Oscar Murillo). The record for a work “in the manner of” or by a “follower of” Caravaggio is $529,650, set at Christie’s Milan in 2006.

“You are buying basically two artists in one painting: Caravaggio and Reynolds,” New York dealer Mireille Mosler told artnet News. “This painting is not in pristine condition, but there are plenty of trophy buyers out there and I trust that it will sell well.”

“If you had a great Caravaggio,” New York dealer David Tunick told artnet News, “it would be estimated for tens of millions. Arguably higher.”

The number of works by Caravaggio (including works described as “in the manner of” or “follower of”) selling at auction has steadily increased since 1998, when just five works sold; 2013 and 2014 each saw 17 change hands.

Tunick said that while he doesn’t doubt the attribution of the Bronzino, “The historical literature tells an awful lot about the shifting sands of attribution. The work has previously been attributed to Andrea del Sarto and Pontormo, then it wasn’t a Pontormo, then it was a copy, and now it’s described by great art historians as a Bronzino. But what will it be called in 35 or 50 years?”

For a look at some of the issues with attribution of Old Master paintings, see A Tale of Two Leonardos and Authenticity of Leonardo’s Virgin of the Rocks Under Scrutiny. And for a preview of the Sotheby’s sales, check out Bruegel, Tiepolo, Reubens Shine at Sotheby’s Old Masters Sales.