Art Market
Why Leo Castelli Paid his Artists Even When They Weren’t Making Work
By 1960, the hero was watching his movement get surpassed by the artists represented by his friend Leo Castelli, a group led by and . And because of this, Castelli opted not to represent de Kooning, a source of tension between the two of them. And yet de Kooning couldn’t deny the dealer’s ability to sell.
“That son-of-a-bitch, give him two beer cans and he could sell them,” de Kooning said at one point. Johns promptly cast two cans of Ballantine Ale in bronze, and Castelli sold them to the taxi baron and celebrated collectors Ethel and Robert Scull for $960.
Such stories about Castelli are legion, but beyond his bond with Johns and Rauschenberg (and , , , and many others), he also shaped the practice of selling art in a way that still resonates today. Castelli was the first to assemble a roster of new, boundary-pushing artists and market them as brands, establishing the modern concept of gallery representation. He was the first to partner with dealers across the country and in Europe, taking advantage of an increasingly global collecting class that wanted work by post-war American artists. In his twilight years, he partnered with a younger generation of dealers, ensuring that his influence would reverberate for decades to come.
What made him such a capable salesman, such that he could literally sell a couple of beer cans to a collector with the pedigree of Scull? Castelli’s eye was legendary, as was his unflagging gentility, and his ability to charm collectors by mixing Old World sprezzatura with Manhattan chutzpah.
Leo Castelli at a Jasper Johns exhibition at Castelli Gallery, 1958. Courtesy of Castelli Gallery.

Leo Castelli at a Jasper Johns exhibition at Castelli Gallery, 1958. Courtesy of Castelli Gallery.

The man was no prodigy. His gallery opened at 4 East 77th Street on the Upper East Side in 1957, when Castelli was already 50 years old, having lived a meandering life that began when he was born in Trieste, the Italian port city. He went to school in Milan, then worked at an insurance company in Bucharest in 1932, where he met and married a woman named Ileana Schapira, with whom he moved to Paris in 1935.
Ileana’s father was rich enough to back Castelli’s first art-adjacent venture, a gallery on the Place Vendôme devoted to modern furniture and decoration. But in its first few months, the gallery swiftly switched from selling ottomans to paintings after Castelli was introduced to Paris’s thriving art scene through a Triestian artist friend. and quickly got involved.
But after Castelli and his wife closed the gallery for the summer of 1939, World War II broke out in September, causing the couple to flee Paris and the gallery. They traveled via Tangier and Cuba to New York, arriving in 1941, accompanied by towers of suitcases and an English nanny for their daughter. In 1942, they moved to the Upper East Side, into a townhouse purchased by Castelli’s father-in-law. Two years later, Castelli joined the U.S. Army in order to become a citizen, but never saw any action; instead of being sent to battle, he spent his military service training at Camp Ritchie in Maryland, and then worked in Bucharest for the Allied Control Commission as an interpreter.
Castelli returned to New York in 1946 and slowly became a fixture of the city’s avant-garde, throwing parties at his apartment, gifting two Dalí drawings to the Museum of Modern Art in 1946, befriending curators and artists, and, by the end of the decade, hosting Willem and at his home in East Hampton. After collaborating with the dealer Sidney Janis on a few shows, he finally opened his space of his own, with the intention of moving beyond the Abstract Expressionists. Castelli was confident that he had an eye for what new art would make de Kooning and his ilk seem dated, and what types of groundbreaking work adventurous collectors would covet even more than what they collected at the time. After shows by Johns and Rauschenberg at Castelli Gallery titillated the New York scene and seduced museum directors in the first few months of 1958, that previous movement was swiftly dispatched.
“There are those unsuccessful Abstract Expressionists who accuse me of killing them; they blame me for their funerals,” Castelli said in a 1966 interview with the New York Times. “But they were dead already. I just helped remove the bodies.”

A new model for gallery representation

The gamble of showing the deeply controversial Johns and Rauschenberg paid off. As Calvin Tomkins wrote in a canonical New Yorker profile of Castelli in 1980, “Jasper Johns’ first one-man show at Castelli’s, in January of 1958, hit the art world like a meteor.” Alfred Barr, the director of MoMA at the time, came to the opening, stayed for three hours, and bought four works for the museum—a decisive vote of confidence in a young artist having his first solo show.
Rauschenberg had the next show, and in the few years that followed, Castelli wrangled Lichtenstein, Warhol, and Judd into his stable, as well as , , , , , , and , among many others. In 2010, New Yorker critic Peter Schjeldahl included, in a review of Annie Cohen-Solal’s biography Leo and his Circle, a telling declaration from Castelli’s gallery director Ivan Karp to the critic Leo Steinberg: “We should discover a genius! It’s been two weeks since we last discovered a genius!”
In order to keep these geniuses, Castelli devised a new model for how to treat his gallery roster—one that was so influential, it’s now referred to as the “Leo Castelli Model.” Under the old system, galleries simply sold the work and split the profit with the artist, a transactional relationship that did not assume the artists would have lifelong loyalty to the dealer. But under the Leo Castelli Model, the gallery and the artist have a bond, with the dealer providing him (it was usually a him) with money for a studio and art-making supplies, and tracking his market to make sure prices don’t get too inflated. The gallery also carefully nurtures the brand of the artist, handling press and public relations, and making sure that they were regularly slotted into the exhibition schedule. One practice of Castelli’s that was not adopted by many of his followers, though, was his insistence on giving each artist a stipend every month, regardless of whether their work was hot at the moment, or if they were regularly making work at all.
In his book Selling Contemporary Art: How to Navigate the Evolving Market, dealer and writer Edward Winkleman riffs on how such an approach started being referred to as the “Leo Castelli Model”:
“Leo Castelli did not invent many of the strategies behind his unparalleled success at selling contemporary art…but he optimized a series of ‘best practices’ for art dealing in a way that was so admired by artists and younger dealers alike that it unofficially became ‘the way it’s done.’ The cornerstone of the model was for mutual trust and loyalty between dealer and artist to guide what was presumed to be a long-term relationship over the inevitable ups and downs of both an art career and the economy’s cycles.”
Indeed, Calvin Tomkins, The New Yorker profile writer, relates a story where Karp suggests cutting Chamberlain’s stipend in half because he was slow making work, and happened to be $40,000 in debt to the gallery.
“How could I?” Castelli said. “He couldn’t get along on that.”

Harnessing a globalized collector diaspora in the U.S. and Europe

The heyday of the Abstract Expressionists in the U.S. was the 1940s, but little of their work was seen in Europe until a decade later, since dealers such as Sidney Janis did not stage shows of their artists across the ocean. But by the 1960s, there was a great amount of interest in American artists among European collectors, perhaps even more so than their stateside counterparts. Among Castelli’s biggest clients was Peter Ludwig, who married into a German chocolate fortune and would eventually establish the world-renowned Museum Ludwig in Cologne to house his collection.
“The American people probably need more time to realize the importance of recent American art,” Ludwig told Tomkins in The New Yorker profile. “The most influential critics in your country were shocked when Lichtenstein first appeared, but the museum in Amsterdam, the museum in Stockholm, the museum in London bought these works in the first moment.”
How did Castelli place work with European collectors, having fled the continent 21 years before? He was among the first to partner with established galleries across Europe and give them a cut of the sales of contemporary art. Castelli’s artists had shows with of Europe’s most prominent dealers, such as Konrad Fischer in Dusseldorf, Gian Enzo Sperone in Turin, and in Paris, the dealer Ileana Sonnabend, who was Castelli’s former wife and had since married the scholar Michael Sonnabend. The two remained on good terms, especially when it meant they could both make money.
Initially, it looked like Castelli was making a tactical error. Castelli made an arrangement with Sonnabend to stage shows of work by Johns, Rauschenberg, Stella, and other Castelli artists, and the terms on which Castelli consigned the work initially appeared to favor Sonnabend over her ex-husband. Karp said that the contract arrangement was “ruinous” to their gallery. But eventually, the strategy paid off for Castelli, for even if he took a loss on some shows, he met transformative collectors building museum-quality troves of work—Ludwig was one of the connections made, for instance. Over the following decades, galleries adopted a similar model of sharing artist representation in different cities, which stands to this day.
Similarly, Castelli partnered with galleries in different cities in the United States, selling work to these regional shops at a discount and sacrificing some of his own profit share in favor of a wider distribution network. And the regional galleries benefitted, too, as they had a steady stream of work to sell to increasingly free-spending collectors in their cities who didn’t want to come to New York to buy. Among the partners were Virginia Dwan in Los Angeles, John Berggruen in San Francisco, and Janie C. Lee in Houston. The arrangement of cutting other dealers in on artists appeared suicidal at first, but it soon paid off.
“It always seems he’s giving up an enormous amount, but then you see that he has been enormously clever, and that he’s more than compensated,” said dealer Irving Blum in TheNew Yorker profile.

Cementing a legacy

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By April 1977, Castelli was staring down 70 and had not taken on a new artist in six years when a new gallery opened up in another floor of his gallery’s SoHo building, at 420 West Broadway. Castelli had never heard of his new neighbor, Mary Boone.
It took two years for the master to visit the young dealer’s space. When Castelli finally ventured downstairs to Mary Boone Gallery, he saw the first solo show by an artist named . “This was a coup de foudre,” Castelli told journalist Anthony Haden-Guest. “Like when I went to see Jasper in ’57 or Stella in ’59. I went in and I saw the clay paintings. And I was just bowled over.”
By 1981, Castelli was co-representing Schnabel with Boone, splitting the dealer’s share 50-50. The arrangement gave the young dealer a heap of clout—and Castelli’s contacts. “Leo has a big backlog,” one anonymous dealer told Haden-Guest. “If he wants to sell something, he can select five or six key collectors from the ten or twenty around the world.”
Those who bought work from Schnabel’s 1981 two-gallery show included Peter Ludwig and the Greek shipping heir Philip Niarchos. Castelli’s mentorship to Boone allowed him to shape the way a new generation approached running a gallery and selling art, and his influence is still felt today. Another early acolyte was Jeffrey Deitch, who helped Castelli sell $2 million in prints to Japanese investors. Deitch was richly rewarded for his assistance selling the prints when he was starting his own space. “Leo realized I would need a list of contacts, so he instructed his assistant to run up a copy of his mailing list and just gave it to me,” Deitch recalled to Cohen-Solal, Castelli’s biographer.
Castelli also mentored Larry Gagosian early in his career, before the young Angeleno went on to become the most commercially successful contemporary art dealer of all time. Castelli hooked him up with artists to show at his Los Angeles galleries in the early 1980s, and connected him to the collectors whose support kickstarted what would become a chain of 16 galleries around the world.
The best assistance could come at the most unexpected times. As Gagosian recalled to WSJ. Magazine, the two were walking around SoHo when Castelli greeted a “completely nondescript gentleman,” in Gagosian’s estimation. Castelli said, “Oh, that was Si Newhouse. He can buy anything he wants.” Gagosian insisted Castelli run back to introduce him to the billionaire Condé Nast owner. By 1988, it was Gagosian at Sotheby’s bidding on behalf of Newhouse when he bought Johns’s False Start (1959) for $17 million, smashing the record for a work by a living artist.
Gagosian paid his respects to the master in 1996 with “Leo Castelli: An Exhibition in Honor of His Gallery and Artists,” one of the first shows at his gigantic Beverly Hills gallery. Castelli, then 88, made it out for the opening. Strolling through the exhibition with a Los Angeles Times reporter, Castelli was clearly charmed by the gesture from the apprentice to the master. When asked if he had any regrets about his life as an art dealer, Leo Castelli, a lion in winter, said he did not.
“What else would I have done?” he said.
Nate Freeman is Artsy’s Senior Reporter.