You couldn’t flatter S.I., and you couldn’t win him over — he made the decision, not you,” recalls Tobias Meyer, advisor to the family of S.I. Newhouse Jr. and famed contemporary art expert and auctioneer. “He was very certain about his judgment in everything — never in doubt — in art and in people.”

Eleven works from the expansive and groundbreaking collection of Newhouse, the late American media mogul and longtime Condé Nast chairman, will be offered this May in Christie’s Modern and Contemporary Art auctions. The works, masterpieces spanning a century, offer a small window into the psyche and limitless passion of the collector, who was known for his impeccable eye and keen decision-making.

Eleven works from the S.I. Newhouse Jr. llection me to Christie’s May auctions

Jeff Koons; Rabbit;1986

Courtesy of Christie's

“He really taught me a lot about what a great collector is,” says Larry Gagosian, owner of international powerhouse Gagosian Gallery and Newhouse’s go-to dealer for decades. “A great collector is somebody who wants to buy art, who wants to do it with a real ambition. It takes a tremendous drive to make a great collection. You have to really fight for stuff, and he was very much up to the task.”

Gagosian remembers in particular Newhouse’s enthusiasm. “We were going to Texas to buy a [Jackson] Pollock...a major drip painting. And there was a lightning storm. This plane [S.I. had chartered] was the smallest jet — you had to crawl to get to your seat, it had half a pilot — and [throughout the storm, [S.I.] was underlining things in Vogue with a yellow marker…I don’t think he even looked out the window. It was like nothing, like taking a ride across town.”

This unwavering focus characterized Newhouse’s acquisition of one highlight in the forthcoming sale — Jeff Koons’s famous stainless steel Rabbit, a breakout sculpture that permanently altered the landscape of contemporary art. Newhouse bought it in 1992 for $1 million, an unprecedented price at the time. Now anticipated to break Koons’s previous auction record of $58.4 million, Rabbit once held a place of pride in the apartment Newhouse lived in with his wife Victoria, an architectural historian.

Eleven works from the S.I. Newhouse Jr. llection me to Christie’s May auctions

Richard Prince; Untitled (The Velvets); 2007

Courtesy of Christie's

Rabbit shared its home with other modernist and contemporary masterpieces, including Cezanne’s Bouilloire et Fruits, estimated to sell in the region of $40 million at the upcoming sale, and Van Gogh’s Arbres dans le Jardin de l’Asile, estimated at close to $25 million. Lucien Freud’s Painter’s Garden, a richly and radically daubed work from 2003, is another standout lot, along with Lichtenstein’s Ben-Day dotted Landscape with Boats, a number of Alberto Giacometti’s masterfully stripped-down sculpted heads, and a Degas bronze of a horse, captured in an instant of motion just as he begins to rear up on his hind legs.

Newhouse relished living with his collection. “He would, on several occasions, take a lot of the masterpieces out,” recalls Gagosian. “And then he’d hang the young artists he’d been buying over the last year or two, and keep some of the more seminal things, the touchpoints, [on view].”

This constantly evolving curatorial spirit, coupled with Newhouse’s relentless initiative, spurred his lifelong pursuit of rare masterpieces, and made him an inspiration for other collectors.

Eleven works from the S.I. Newhouse Jr. llection me to Christie’s May auctions

Vincent Van Gogh; Arbres dans le Jardin de l’Asile; 1889

Courtesy of Christie's

“Wherever S.I. paid attention, everyone else did,” says Meyer.

“I took many people up to his apartment...David Geffen [and others], and…when they saw what he had it was always like a lightbulb turned on, like ‘Wow, look what you can do if you have the means and the energy,’” Gagosian recalls.

“When S.I. Newhouse came in, the world stood still,” remembers Alex Rotter, Christie’s chairman of postwar and contemporary art. “And when he was on the phone during an auction, you knew he was just going to buy. There were people who were richer than he was, but there was no one who was willing to go for it like he was. Not because he had more money than anyone, but because he had more passion than anyone.”

Meyer concludes, “He didn’t live in the past; he lived in what is possible. He kept his eyes open.”

Works from the Newhouse Collection will be auctioned during the week of May 13 at Christie’s New York in the Impressionist and Modern Art Evening Sale and the Post-War and Contemporary Art Evening Sale. The works will be on view to the public at Christie’s in Rockefeller Center from May 4 through May 12.

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