In March 2019, a 42-foot-high billboard was installed on a Park Avenue building, unavoidable to passersby, and featured an aging white man and a slightly younger blonde woman. Most could chalk up the appearance of such a thing to some New York oddity, but to anyone in the know, it was the latest barb in a fight that had shaken Manhattan’s upper crust to its core. The billboard showed the real estate developer Harry Macklowe and his new wife, Patricia Landeau, whom Harry had reportedly been having an affair with while he was still married to Linda Macklowe, his wife of five decades.

It was the apex of the most high-profile New York–society divorce since, sigh, Donald and Ivana—one that got some final closure Monday when Sotheby’s auctioned off the first part of the collection in a blockbuster sale that brought in $676.1 million, more than any single-collection sale in the 277-year history of the auction house.

Harry and Linda were real estate titans laid low by bad bets and a wobbly economy. But even if his deals for Midtown skyscrapers blew up in the recession and sent the couple into massive debt, all the while they had been investing in something much more lucrative than buildings. During the years when her husband tangled in a variety of big-ticket Manhattan real estate transactions, Linda Macklowe worked as a curator, heading up the programming at public art spaces in the city and Riverside. Once the family had the means to start building a collection of their own, Linda started trophy hunting, and became the person every dealer wanted to sell to.

A gallery owner seeks out the most secure collection, and the Macklowes almost never flipped a work after they bought it. The idea was the collection would stay secure forever.

“Usually, the dealer with their name on the door wouldn’t rush out of their office to greet any random collector if they come in unplanned,” said a high-powered adviser in the hours before the sale. “When Linda Macklowe came in, they would run off of their desk and into the gallery.”

Over decades, the couple meticulously built up a stunning collection of works by dead and canonized 20th-century postwar titans, often cherry-picked from the most storied art collections on earth. They bought a Jackson Pollock and a Robert Rauschenberg previously owned by the late Condé Nast president Si Newhouse, a Willem de Kooning once owned by Dallas mega-collector Howard Rachofsky, and a magnificent Mark Rothko owned by Houston oil heiress Sarah Campbell Blaffer.

Equally impressive was the full trust in the living artists of the day, and their ability to foresee which artworks the next generation would deem masterpieces. The Macklowes bought a work by Jeff Koons from International With Monument in 1986, a massive Brice Marden directly from Mary Boone Gallery in 1988, and a gripping, challenging Robert Gober sculpture, Untitled (Butt), from Paula Cooper Gallery in 1994. None of the works ever changed hands again.

By the time Cy Twombly was making gigantic eye-popping three-paneled works for a show at Gagosian Gallery in 2007, Larry Gagosian could have sold all six of them, each priced at $5 million a pop, to any collector on earth. He sold one to the Macklowes, who installed it in their apartment until their divorce.

“There was no reason to think this collection would ever come to auction,” said an art consultant to a major collecting family. “Which makes it such an unprecedented sale.”

The long road to Sotheby’s took years. The divorce proceedings effectively began in the spring of 2016, but when the hearings began in court, the question of how to divide the art collection became the main sticking point in the split. First, the collection had to be officially appraised, and according to court documents, each team hired their own appraiser to assess the worth of each work. Linda tapped Christopher Gaillard, chief appraiser of Gurr Johns, while Harry roped in Elizabeth von Habsburg, managing director of the Winston Art Group. 

Furthermore, Harry and Linda each hired their own swashbuckling rainmaker to act as their own adviser as they fought it out in court. Harry got Tobias Meyer, the former Sotheby’s contemporary-art head and principal auctioneer known for brokering $100 million deals on single pictures, and Linda got Laura Paulson, the former Christie’s chairman who now heads up Gagosian’s art-advisory arm. Documents show that the couple would argue over the value of a work, with the quibbling every bit as toxic as the negotiations over which houses and apartments each would win.

After appraisals found the horde to be worth anywhere from $625.6 million and $788.7 million, another art market macher, Acquavella director Michael Findlay, parachuted in to act as the court-appointed “receiver,” whose role was to figure out how to sell it off for the highest-possible total. More than a year later, Sotheby’s announced that it had nabbed the prize.

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