David Rockefeller kept a $90 million Picasso nude in his living room, wedged between windows that overlooked East 65th Street. For him, art was meant to be lived with, not hidden away.

Rockefeller, the last surviving grandchild of Standard Oil Co. founder John D. Rockefeller, had a long-standing affinity for modern art and spent the better part of a century collecting works by Paul Gauguin, Diego Rivera, Henri Matisse, and others. He was born wealthy, but over time his habit contributed significantly to his personal fortune.

Particularly in the last decade of his life, as values in the art market ballooned, his paintings began to “constitute a very good portion of his personal estate,” says Peter Johnson, the Rockefeller family’s official historian. Starting on May 8, when Christie’s will auction off the collection over the course of a week of blockbuster sales, we’ll find out just how big that portion is.

When Rockefeller died last year at the age of 101, his collection included at least four paintings by Claude Monet; stunning works by Edward Hopper, Georgia O’Keeffe, and Georges Seurat; and hundreds of other treasures, including a dinner service Napoleon took with him into exile on Elba.

Some of the objects were purchased for pennies, compared with their worth now. “I think David expected that the value of a Picasso would increase from 1967,” Johnson says. “Did he think it was going to increase a thousand times? No.”

In 2007, for instance, Rockefeller sold a painting by Mark Rothko at Sotheby’s in New York for almost $73 million. He’d bought it in 1959 for $10,000.

Rockefeller’s wife, Peggy, died in 1996. Together, they’d planned on donating most of their personal wealth to charity. Decades ago, they arranged for 13 works to go to New York’s Museum of Modern Art, which was co-founded by his mother, Abby Aldrich Rockefeller. But in the long run, Rockefeller determined that most organizations needed his money, not his art.

So, with the exception of a few individual bequests—the Metropolitan Museum of Art in New York got a painting by Edouard Manet, for instance—he decided that his collection, along with everything else, would be sold. The proceeds will go to 11 named organizations, including Rockefeller University, Harvard University, the Maine Coast Heritage Trust, and the Council on Foreign Relations. Per the will, a number of other charities will also benefit.

Ultimately, the decision to sell the art after Rockefeller’s death came down to taxes. “A lot of the art was purchased for good prices in the 1940s, 1950s, and 1960s,” Johnson says. “But the art market just went bonkers since then.” The Rothko that Rockefeller sold in 2007, for instance, realized a profit of about 730,000 percent. “You can imagine what the capital gains tax was,” Johnson says. So Rockefeller stuck to his original plan: to leave the art in his estate and donate the proceeds to charity. That way, Johnson says, “there was no tax to them.”

After that, it was up to a team of professionals, armed with the ever-expanding valuations of Rockefeller’s holdings, to make it happen. Given the scale of the estate—there are 67 dinner services, for instance, not to mention an immensely valuable collection of wooden duck decoys—cataloging all of it and figuring out how much it could be worth was a herculean undertaking.

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