Cultivating artists, collectors and dance partners with the Leo Castelli Gallery model

The current financial value of NFTs might make it seem otherwise, but the work of virtual galleries and digital artists need to fight for legitimacy within a much broader cultural perspective. Challengers should not lose sight of an opportunity to improve the Art world. A disruptor's job is to challenge norms rather than take residence within an old system. So while NFTs and virtual galleries are still outliers, they might take inspiration from past outliers in art who created valuable new markets while achieving cultural legitimacy. 

There was a time when all American art was also sidelined, and it took a great diplomat who, while everyone else was about competition, he was about alliances. Our immigrant instructor was steeped in art history and managed to weave those past stories together with future fortunes. He was 'a tie salesman', a pioneer of the mega gallery, a former secret agent, the ultimate mythmaker, the Godfather of America's contemporary art world, and the quintessential late bloomer: Leo Castelli.

"New work never threatens the past, only the present that is yesterday." - Robert Rauschenberg.

Trad art.

One hundred years ago, Europe/Paris alone was synonymous with serious, professional art. Europe had centuries of masters and movements from Romanticism to Surrealism. The Robber barons of the industrial revolution imported their reputation in the form of old master paintings. 

This isn't to say that there was no artistic talent in America; on the contrary, world war 1&2 had sucked up the lion's share of creative talent and work into America, especially NYC. 

Post-war, while everyone else was recovering, the US was a boiling pot of creation. Artists such as Jackson Pollock, Mark Rothko and Willem de Kooning expressed that energy as an exciting new form of art in abstract expressionism. 

But outside America, abstract expressionism was regarded as an American fad. People were losing their minds in accepting that grown adults could produce canvases that looked like the mindless strokes of children. Some felt attacked and insulted in contemporary comparison to the decades-long journey of masters perfecting a figurative or abstract skill. Further movements weren't possible by Americans, and it was a dead-end, a bubble that would pop and then we'd get back to the evolving tradition of European artistic mastery. 

When something looks 'so' different and seemingly comes out of a void, it is seen as an oddity. But, capitalising on the momentum of abstract expressionism, it took business visionaries such as Leo Castelli to build an ongoing new market for artistic talent and collectors. 

Audiences outside the US didn't want to be left behind. They believed in an evolving art tradition within Leo's artists. His gallery and artists contextualised an idea of the world's displacing European talent through World wars. But the Bauhaus lived on through Josef Albers teachings at Black mountain college and now through Robert Rauchenberg's shocking new work from a new world. 


An overnight success, 50 years in the making

Remarkably, Leo Castelli (1907–1999) started his career late in life; his gallery opened when he was nearly 50. But, in truth, Leo had long had an active interest in art long before he started his NYC gallery. 

During the first quarter of his life, Leo's second name was Krausz. Under the compulsion of Mussolini's government, which required the Italianization of family names, his father adopted his wife's maiden name. Although being born and married into sufficient means, the political turmoil of World war 1&2 jostled a young Leo Castelli around Europe before he was forced to emigrate to NYC. Not many gallerists can ever claim time in the American secret service, but that's precisely how he secured his citizenship in exchange for his service during WW2, owing mainly to his affable nature and speaking five languages.

After meeting his wife in his late 20s, Castelli repeatedly tried to represent artists as both a side hustle and intermittent full-time gig. In his first gallery in Paris, he first tried out his innovative stipend model called 'artist fund', where the artists all pitched in to support one another through challenging periods. Unfortunately, his gallery in Paris never really got off the ground due to the bad timing of the encroaching war. After the war, he tried to represent the gallery as an American counterpart, but it was a crowded secondary art market. 

After his military service, Leo lived a life blessed by his father in law, who blessed him with a house in NYC and a job for ten years as a manager in his clothing factory! During this time, he became infatuated with the art museums of NYC and surrounded himself with the country's most notable artists. The majority of artists for which he would gain initial acclaim before opening his gallery he met before opening his gallery as he made it a habit to frequent artist studios. Castelli met Jasper Johns when he was visiting Robert Rauchenberg's studio and popped into the communal fridge in John's studio for ice. He offered Johns a gallery show on the spot and prioritised it over Rauchenberg's! When Castelli gallery eventually did host Rauchenberg's exhibition, it only made one sale, and that was to Leo Castelli. We all catch a break at different points in life, make sure and do all you can to put yourself in a place where when opportunity comes knocking, you want to go where it can take you.

Lessons from Leo for Gallerists

Skin in the game

"Leo came to me and offered to give me a regular monthly stipend, guaranteed for three years, and told me that he would not expect to sell anything during that time. I never expected to find anyone willing to support experimental work. I could not believe it. It was like getting a Rockefeller grant. Leo has always been generous, supportive, intimate, and friendly, a throwback to another century." - Robert Rauchenberg.

Castelli gallery distributed regular monthly stipends over three, four, even five years that freed artists up from non-creative concerns - "as French publishers used to do for their authors," he gamely pointed out. Leo considered himself a patron of the arts and acted similarly to great patrons of the past, such as the Medicis. This, of course, made artist desertions extremely rare.

Leo expected no less conviction from his business partnerships. Even his gallery customers occasionally evolved into partnerships as he built on their appetite. For example, Joe Helman's relationship evolved from the collector into a dealer and then a patron through monthly checks. 

"When I was in St. Louis, I [contributed to stipends for] Don Judd and Richard Serra and Bruce Nauman, and part of the Stella payment. This was an outgrowth of my paying him $500 a month. Then after I became a dealer, we started sharing artists…" - Joe Helman.

In this case, a customer eventually started assuming some of the risk of supplying that upfront stipend, presumably for early access to artwork. 

Don't worry about your slice; just bake a bigger pie 

Leo Castelli became a figurehead of American Art because he was willing to be a conduit. 

"He was interested in artists; he would come to all the parties. He especially liked to dance: that's how he got involved with artists." But, she continued more critically, "he was a tie salesman, he had a factory! It was his wife, more than he" - Ernestine Lassaw.

Success is a team sport. "Castelli had the ear, and Ilena the eye."* Regardless of their roles, collectors were demanding more 'American hero' artists and Castelli gallery was supplying them as a team. Leo and his wife fostered communities everywhere they went by paying their way through dinners and alcohol far outside of what artists could afford and taking people on holiday. They used their means where they couldn't contribute their artworks. In exchange, they became part of an exclusive club of artists (The Club, 39 East Eighth Street, 1950), which formally met to candidly debate new myths and how they should redefine themselves for a new generation. Leo and Ileana Castelli, together with the dealer Charles Egan, were the only non-artists to join as founding members. Castelli would later capitalise upon this information asymmetry through his network and knowledge. 

At the time art was sold from 57th Street galleries in NYC. But Castelli was globally ambitious and relied on a network of satellite dealers. Castelli Gallery achieved great success in NYC, but its global network brought its unparalleled deal flow to a market they controlled. When Leo and Ileana divorced, they remained close as she deployed the same technique in Paris. The unsung art hero, Ilena's poor father, again foots the bill as she took three years to wine and dine artists, host shows and generally turn her gallery into a bastion of American art within Paris. We saw people, and people saw us. That's what counted." - Ileana Castelli.

Ilena would even send collectors to NYC at Leo's cost. Castelli made a deal with his ex-wife where she effectively became a reseller of any works he didn't sell from his NYC gallery. He then extended this same model across America, and this opened a new incoming market to Castelli to continually rejuvenate himself through new trends, talent and dealers. Castelli Gallery became a brand and a uniquely gated market. Leo was a sole gateway to the sacred works of these great American artists, second only to museums. 

There was a limited amount of artwork that artists could produce. Roy Lichtenstein typically sold eighteen to twenty-five paintings a year at high prices. By 1990, his Reflections On "The Artist's Studio" went for $1,600,000; his total sales for that year topped $8 million, on which Castelli received his share of $800,000.

Collectors would have to compete for a privileged position at one of Lichtenstein's annual works. Not just for their walls but also their wallets. After the war, America passed tax laws that made it advantageous to give things to museums. 

"The [individual] tax rates got as high as 78 per cent. So you would have a picture for, say, $100,000, and you'd get a $200,000 appraisal on it, and you'd get seventy-eight times two is a $156,000 tax write-off for this $100,000 picture!" - Robert Pincus-Wittenm, 2008

Leo Castelli was the world's first mega-gallerist because of his mega network. The meteoric rise in prices over the next 50 years has much to thank Castelli for in laying a template for artist/gallerist/collector co-operation and market-making. However, Leo didn't just aspire to sit in an NYC gallery; he evolved art's tradition through new models and new heroes. Castelli's network of galleries created a new globally networked model that represented how he saw the world and cultivated a community of dancing partners everywhere he partied. 


  • Leo and His Circle: The Life of Leo Castelli by Annie Cohen-Solal
  • *Boom: Mad Money, Mega Dealers, and the Rise of Contemporary Art
  • ILEANA SONNABEND Ambassador for The New - MoMA
  • Robert Rauchenberg: Man at work, BBC/RM in association with the Guggenheim Museum and Ovation; dir. Chris Granlund (Chicago: Home Vision Arts, 1997)
  • Picture from Leo's brithday party in 1985 courtesy of Gallery98  
  • Andy Warhol, Portrait - Leo Castelli, 1979, Mazzoleni collection, Bergamo; EF Arte, Milan.
  • Photo of Leo Castelli with Willem de Kooning in back by vaccora photo
  • Photo of Leo Castelli with Larry Gagosian & Charles Saatchi on holiday in st Barthelemy by Jean Pigozzi, 1991