In the salad days of his art collecting, back in the 1960s, the magazine publisher S.I. Newhouse Jr. started out modestly, at one point paying the dealer Betty Parsons on an installment plan.
His purchasing ramped up quickly from there, and Mr. Newhouse, the Condé Nast owner who died in 2017 at 89, eventually used his billions to amass a large collection of blue-chip modern and contemporary art.
“He had the best eye and the best collection of postwar paintings ever put together,” said his friend David Geffen, the entertainment mogul, who added, “I bought a lot of it.”
The fact that Mr. Newhouse was willing to part with well-known works by the likes of Jasper Johns and Willem de Kooning for the right price illustrates the fact that the collector, known as Si, was never overly sentimental about his trove. He was always happy to trade up or cash out.
Now his family is following suit, selling 11 big-ticket works at Christie’s New York, spread over two evening sales in May. The auction house estimates that the group is worth some $130 million. (Last November, the family sold a Francis Bacon work, “Study of Henrietta Moraes Laughing,” which brought $21.7 million at Christie’s in Manhattan.)
The strength of the lineup is reflected in the fact that a choice Cézanne still life in the bunch — “Bouilloire et Fruits” (“Pitcher and Fruit”) from 1888—1890, estimated at $40 million — is considered only the second-most valuable of the works. It goes up for bid May 13 at the Impressionist and Modern sale.
The marquee Newhouse lot is Jeff Koons’s sculpture “Rabbit” (1986), estimated to fetch between $50 million and $70 million when it is offered May 15 at the Post-War and Contemporary auction. The shiny metallic bunny is one of only four in existence, and the last in private hands.
If it meets the house’s expectations, it could surpass the highest price paid for a Koons at auction, $58.4 million for “Balloon Dog (Orange)” (1994-2000), sold at Christie’s New York in 2013.
“I’m a firm believer that we will have a record for Koons,” said Alex Rotter, the chairman of postwar and contemporary art at Christie’s, which is sending a selection of the Newhouse works on tour, beginning this week in Asia to coincide with Art Basel Hong Kong.
Rounding out the top Newhouse lots are Vincent van Gogh’s “Trees in the Garden of the Asylum” (1889), estimated around $25 million; Roy Lichtenstein’s “Landscape with Boats” (1996), $7 million to $9 million; Andy Warhol’s “Little Electric Chair” (1964—65), $6 million to $8 million; and Lucian Freud’s “Painter’s Garden” (2003), $4 million to $6 million.
Works from the collection by Giorgio Morandi, Richard Prince, Alberto Giacometti and Edgar Degas are also going on the block.
“When he wanted something, he was passionate,” said Tobias Meyer, the former Sotheby’s principal auctioneer who now works as a private dealer and is advising the Newhouse family on the estate.
Mr. Meyer got to know Mr. Newhouse 20 years ago, after the collector picked up Warhol’s “Orange Marilyn” (1964) at Sotheby’s for $17.3 million in 1998.
“Once he made up his mind, he was not in doubt,” Mr. Meyer said.
He noted that the collection was hardly being depleted by the sale.
“They’re selling a fraction of the collection, and Victoria is still buying,” Mr. Meyer said, referring to Mr. Newhouse’s widow.
Mr. Newhouse was something of a legend on the auction scene. When he wasn’t overseeing a magazine empire that included Vanity Fair, The New Yorker, Vogue and many other publications, he was frequently on the hunt for art, usually bidding by phone.
“Si said to me that he always gets what he wants because he will not stop bidding,” Mr. Geffen recalled. “We competed for a number of pictures, and he always won.”
The friendship did yield some benefits for Mr. Geffen, who called Mr. Newhouse a mentor. He said that he bought some 20 artworks from Mr. Newhouse over the years, including paintings by Lichtenstein and de Kooning.
Another work that made its way to Mr. Geffen’s collection was Mr. Johns’s “False Start” (1959), which Mr. Newhouse bought for $17 million at Sotheby’s in 1988, then a high for a living artist.
Illustrating the chummy relations among billionaire collectors, who trade modern masterpieces like baseball cards, Mr. Geffen later sold “False Start” to the hedge fund titan Kenneth C. Griffin and his former wife, Anne, for $80 million in 2006.
The pictures and sculptures that the Newhouses held onto quickly filled up their Upper East Side townhouse. They had to sell off some of them when they moved to a large apartment overlooking the East River — a downsizing, at least in billionaire terms.
“Si loved the hunt for art, the pursuit,” Ms. Newhouse told Mr. Meyer in a video conversation made for Christie’s, adding that he enjoyed that part as much as living with it.
“He never entertained the idea of keeping the collection together,” she said. “On the contrary, he went out of his way to change the collection. He was constantly buying and selling.”
Those who saw the collection in situ came away impressed. “Their apartment was all about the art,” Mr. Rotter said. “The art wasn’t hanging there as decoration — it was the essence of the place.”
Mr. Newhouse arranged the works in his homes himself, never relying on expert advice.
In particular, honing his connoisseurship drove Mr. Newhouse. He read many art publications in an effort to educate himself and keep current.
The couple often went to see Mr. Johns in Connecticut or lunched with Mr. Freud, enjoying the social aspect of being friends with artists while also trying to refine their knowledge.
“The minute he saw a painting that he thought improved on an artist’s work that he had, he would acquire it and very often deacquisition the painting that was not quite as excellent,” Ms. Newhouse said.
Her husband’s interests also shifted late in his life. Though the postwar art of his own time was his focus for decades, he started embracing late 19th-century painters like Cézanne and van Gogh, now going up for auction.
“It was a natural trajectory toward the ancestors of the artists he started with,” Mr. Meyer said.
Despite all the valuable works that passed through his hands, even Mr. Newhouse had a regret or two.
“He had several Pollocks over the years, but he missed one,” Mr. Meyer said of “The Deep” (1953), which ended up at the Centre Pompidou in Paris. “He once stood in front of that picture and said, ‘That’s the one that got away.’”