When the estate of American writer and collector Gertrude Stein came up for sale in 1968, David Rockefeller Sr. formed a syndicate of fellow Museum of Modern Art trustees to buy it.

The members, including William S. Paley, Nelson Rockefeller and John Hay Whitney, agreed to draw numbers from a felt hat to determine the selection order. Rockefeller drew the first pick.

His choice: Pablo Picasso’s “Young Girl with a Flower Basket”, a tender and haunting depiction of a nude with a basket of red blossoms. Painted in 1905 during the artist’s Rose Period, it depicts a waif who was selling flowers around Montmartre at the time.

Art fairs are popping up everywhere from Hong Kong to New York – do they make money?

“That probably represented the most expensive single set of investments he made in art,” said David Rockefeller Jr., the late philanthropist’s son.

Now the work stars in his parents’ collection going on the block starting May 8 at Christie’s. The Picasso, estimated at about US$100 million, is the highest valued of more than 1,500 Rockefeller lots, which include other Impressionist masterpieces, duck decoys and the dinner service that Napoleon took to his exile in Elba.

The painting is among 45 Picasso works estimated to fetch more than US$305 million at New York auctions in the next two weeks. They represent a wide variety of styles and price points. Sellers include embattled billionaire casino mogul Steve Wynn and the estate of Joan and Preston Robert Tisch.

That’s a “value buy” compared to the Rockefeller nude, considering they were done the same year
Brooke Lampley

“Picasso is collected across the globe,” says Nicholas Maclean, a co-founder of Eykyn Maclean gallery in New York and London. “For most people when they are starting out, he is the artist they look to buy.”

With US$212 million of Picasso works having already sold at auction this year, according to Artprice.com, 2018 is shaping up as the best for the Spanish master. The current annual record of US$568 million was set in 2015, when his Les Femmes d’Alger (Version O) fetched US$179.4 million, becoming what was then the auction record for any artwork. It was dethroned in November when Leonardo Da Vinci’s Salvator Mundi fetched US$450 million.

5 of the world’s best art hotels

Christie’s has 17 Picasso works, including three in the Rockefeller sale, estimated at more than US$225 million. Sotheby’s will offer 28 pieces expected to fetch US$80.6 million to US$117.2 million.

Wynn is parting with Picasso’s 1943 self-portrait in a striped sailor shirt, Le Marin. Estimated at about US$70 million, it will be offered during Christie’s evening sale of Impressionist and modern art on May 15.

Sotheby’s top Picasso, to be offered on May 14, is Le Repos, a 1932 portrait of his lover estimated at US$25 million to US$35 million. The work fetched US$7.9 million at auction in 2000, according to Artnet. The auction house also scored a 1905 gouache, Famille d’Arlequin, estimated at US$12 million to US$18 million. It sold for US$9.8 million in 2007.

That’s a “value buy” compared to the Rockefeller nude, considering they were done the same year, says Brooke Lampley, vice-chairman of Sotheby’s global fine arts division.

Want more stories like this? Sign up here. Follow STYLE on Facebook, Instagram and Twitter