Stefan Simchowitz was 6 years old when his parents divorced, and his mother, the artist Shirley Sacks, took him with her when she left South Africa for England. Then when he was 11, his parents sent him to St. John’s College back in his native Johannesburg, where he was bullied for his small stature and his English accent, but mostly, despite his daily presence at mass, for being Jewish. After a year, he was fed up with the bullying so they sent him to the Jewish day school King David, where he was promptly bullied for being Christian.
The bigger boys broke his leg in four places and dragged him around a soccer field. Even with his leg in a cast, they stole his lunch and ate it. He got even. He began to fill his lunch box with pork pies from Woolworths, only he removed the labels so they looked homemade. At the end of the year, he left the labels on, so they’d know what they’d been eating.
He started to take karate under Malcolm Dorfman, a member of the elite sensei group known as the Hornet’s Nest, and traveled with him to Japan and then to America.
“Once I recovered, I made a vow to myself never to let people fuck with me ever again,” he said.
In March, New York magazine art critic Jerry Saltz wrote a blog post that called Mr. Simchowitz, now 43 and an art adviser and collector, “the greatest art-flipper of them all” and “a Sith Lord from the Brotherhood of Darkness” after an innocuous Q&A about Mr. Simchowitz’s business practices ran on a website that sells art editions. In an earlier age, those practices might have seen him likened to an impresario. Instead, the dealer Gavin Brown responded to Mr. Saltz’s post on Facebook with the image of a decapitated horse head, and commenters piled on with their agreement. That week, Mr. Simchowitz appeared on the Approval Matrix, at the upper corner of Highbrow and Despicable, right above an item about human rights abuses in Saudi Arabia.
He fought back on social media, which he’s normally a big booster of, but “at this point in the critical conversation, the amount of critics who are aligned with Jerry is astonishing,” Mr. Simchowitz said. “There’s nothing I can say or you can write that’s going to change their point of view. In light of this era of art info-tainment, this is my role, that is my caste, these are the robes I have to wear. I’m Shylock.”
Like Shylock, what he does is not new; it is the how that causes problems (though thankfully, flesh does not enter into the equation). Over the past eight years, he has worked with some 30 unestablished artists, buying young, early and in bulk, often before anyone knows their names. He puts the size of his own collection at around 900 pieces and still actively works with around 10 artists, whose names he can “write in an envelope and you can open it up in three years, they’re going to be huge.”
He has collected and sold Oscar Murillo, Kour Pour, Sam Falls, Jon Rafman, Amalia Ulman, Petra Cortright and Artie Vierkant, to name a few; these names are on the lips of every speculative collector at the moment—a credit to either his eye or his business sense.
What riles the art world about Mr. Simchowitz is his flipping—an art world term that means quickly selling a work for profit, but Mr. Simchowitz doesn’t see it that way. When Adam Lindemann sells a Jeff Koons for a profit of $20 million after owning it for one year, as he reportedly did in 2007, that’s flipping. Mr. Simchowitz sits on his collection until the artists are popular, then profits on quantity. Last year, he said he did $20 million in sales, but that figure was spread out over, he said, some 1,000 transactions. The margins are low, and he reinvests everything in his business.
“I had lunch with my father yesterday, and my father always shouts at me, because I’m always short on money, I can’t pay my taxes,” Mr. Simchowitz said. “He said, ‘Jerry calls you a flipper! I wish you were a flipper! I wish you were selling more art!’”
Unlike most art galleries, Mr. Simchowitz will sell to anyone, friends from his Hollywood days like Orlando Bloom and Harvey Weinstein, people he met during his time in Silicon Valley like Sean Parker, poker players he’s met through friends, even people he’s met on Facebook.
“If he says to buy something, I buy it,” said Enrique Murciano, an actor and producer who met Mr. Simchowitz years ago at a dingy coffee shop outside Beverly Hills, “the slums of Beverly Hills,” where Mr. Simchowitz still lives. “I don’t need to know the size. Yes, many times I’ve bought things without liking or disliking it or even seeing a picture. I bought Oscar Murillos when they were $500, Joe Bradleys when they were $6,000, Ryan McGinleys when they were basically free.”
Even through the haze of the art world’s vitriol, it’s hard not to be charmed by Mr. Simchowitz, who graduated with a degree in economics from Stanford in 1992 and tends to end sentences in philosophical diagnoses like “what is artificial is sacred, and what is truthful is profane, and what I do is profane in the eyes of the art business.” He can rattle off such thoughts for minutes at a time and is unsuited to the Q&A format. Though mostly British, his accent has a friendly colonial bounce that really sells it when he calls people who decline to be associated with him chickenshit.
He has a head by Brancusi and a body by Botero. He dresses eclectically, t-shirts and sweatshirts that don’t look expensive even though they are, and favors the designer Paul Harnden, “not the kind of shit you get at Barneys.”
His partner, Rosi Riedl, is 40, an Austrian-born, Australian-raised former model who often leans around him as if to be closer and wears a gray pixie cut. (Friends from earlier years in Los Angeles say he used to hang out at nightclubs like downtown’s Vertigo, where he never drank nor was bashful about talking to the most beautiful woman in the room.)
The two met at a beach party in the ’90s where he asked for her number and were married for six years before divorcing but staying together. The relationship is not open but “flexible,” because, Mr. Simchowitz said, they grew tired of living by the rules of a system. “All systems essentially make you unhappy and are unsuccessful because you follow a set of prescribed rules, you follow a status quo that is meant to make you unhappy, you create unhappiness, and then you sell someone ADHD drugs. I really believe all systems are the same, whether it’s nature, science, philosophy or art.” The two have a young son who is comfortable talking to people in their 20s and accompanied Mr. Simchowitz to Colombia in 2012, when Mr. Murillo wanted to show him his hometown.
Mr. Simchowitz lives with his family in a one-level home uncannily close to Beverly Hills proper, zip code 90048, which is owned by Mr. Simchowitz’s father, Manfred—a distinguished art collector whose former wife, Jennifer, sat on the board of the Los Angeles Museum of Contemporary Art until recently. Artists often visit the house, which is where Stefan does most of his work. Day to day this consists of his making calls with hands-free ear buds amid the banana fronds that drip down into the small courtyard, the garage and office in the back bearing the sign “SIMCO” spray-painted over the door.
Though still physically relegated to the garage behind his house, SIMCO has expanded. Mr. Simchowitz recently brought in five staffers—Ms. Riedl’s mother among them—to help with his sales and in six months will open a space with the Rome-based Depart Art Foundation in West Hollywood. He doesn’t want there to be any desks, maybe sofas instead, a place to hang out and see art.
“I don’t want it to be an aircraft carrier,” he said. Normal galleries are aircraft carriers, outmoded in the age of drone warfare. In a few years, he said, his ideal operation will more closely resemble the CIA.
He is given to analogies and exaggeration. The first time I met him at his house, he likened himself to a beehive, the Maginot Line, an enema and the Chinese Monkey King. One dealer familiar with Oscar Murillo’s market, who wanted to speak anonymously because the gallery still does business with Mr. Simchowitz, said that Mr. Simchowitz can’t own more than 16 or 17 works by the artist. Mr. Simchowitz, on the other hand, has been known to tell people he owns 34. (He declined to say how many he owns for this story.)
He sees his buying as almost paternal. He pays younger artists when no one else will, and he and his associates have many stories about the artists he has helped out of squalor. Christian Rosa, for example, needed not only a studio but also an immigration lawyer. Mr. Simchowitz reportedly helped him with both. Lance De Los Reyes even needed a dentist and Mr. Simchowitz helped him with that. When Mr. Simchowitz met Parker Ito (whose work sold at a February auction in London for $93,594 over a high estimate of $25,000), he had a day job painting oil derricks near LAX, Los Angeles County still a surprising source of untapped crude.
Mr. Simchowitz says he is drawn to artists who lack pretension. In 2011, he wandered out of a show at Los Angeles’ David Kordansky gallery and into a smaller one across the parking lot at Mihai Nicodim, a group show that included Mr. Murillo. The artist walked across his own canvases to shake Mr. Simchowitz’s hand. Ms. Riedl had recently put Mr. Simchowitz on a budget, but he had to have them all. He bought all the Murillos from the show and called up Hilary Crisp gallery in London, which had just had a summer show with Mr. Murillo, to see if he couldn’t buy more. He could.
The traditional job of an art dealer is not only to sell but to sell to the right person, someone who would part with a work only to gift it to a museum, not to make a profit. But as art fairs have proliferated and the consumer base widened, through auction record absurdities or the ever expanding coffers of the 1 percent, the past decade has seen the birth of a new art world, one in which some works of art are also a lottery ticket. If that’s the case, why not make sure you get one with better odds?
Smaller galleries in formerly minor European cities like Frankfurt and Brussels now host shows to all the soon-to-be superstars, rather than someone obscure, and these tend to sell to all the usual suspects, rather than local collectors. The international buying mass must have the new lottery ticket pieces, must have them now. The new system has in fact led to many people doing what Mr. Simchowitz does.
Mr. Simchowitz, who is equal parts collector and dealer, says he still buys more work from galleries than he does from artists’ studios. If a gallery declines to sell to Mr. Simchowitz and his ilk, they are said to start LLCs and use proxy buyers, usually consultants, to score an entire show. They will not be denied, though Mr. Simchowitz says he’s never used LLCs.
And this self-righteousness is what irks the art world most about Mr. Simchowitz, even more than his flipping. He is vocal in his criticism of the current system and dogmatic about manipulating it. If you ask him who his favorite writers are, Plato tends to end up on the list.
No one speaks to the hypocrisies of the art world better. He can tell you every supposedly noble collector who has flipped a work in a moment of weakness or has himself speculated.
“It’s like those horror movies where someone runs into a room and locks the door behind them only to discover that the vampire is actually in the room with them,” he said. “They think I’m the bad guy?”
“They made me,” Mr. Simchowitz explained to me at his home, as the sunset turned the courtyard orange. “They weaponized me.”
The dealer Zach Feuer first met Mr. Simchowitz in 2007, around the time he started collecting. Mr. Feuer had “this crazy, unsalable” installation by Justin Lieberman up at his Chelsea gallery, and Mr. Simchowitz, who, Mr. Feuer said, “didn’t really know what he was doing” at that point, bought it. One tends to make conversation with people who do such things, and when Mr. Simchowitz said he was from Los Angeles, Mr. Feuer mentioned that he was headed there the next day for another show by Mr. Lieberman.
When Mr. Feuer arrived at the airport, Mr. Simchowitz was there waiting for him, with a small dog under each arm. He gave one to Mr. Feuer and explained that airport security wouldn’t let him through with both. Dazed, Mr. Feuer took one and followed him through to the gate. “People probably thought we were a couple,” Mr. Feuer said.
Mr. Simchowitz had not only changed his ticket but had also arranged to have his seat next to Mr. Feuer’s (explaining as they sat down that he has a good travel agent). All the way to California, Mr. Simchowitz quizzed Mr. Feuer about what he thought about certain artists, probably 100 of them.
At the time of this flight, Mr. Simchowitz was in talks to sell a company he co-founded, MediaVast, to Getty Images for $200 million. MediaVast’s crown jewel at the time was WireImage.
“We took a very fragmented business,” Mr. Simchowitz said, “of not paparazzi but people who were hired to cover different events, and we said, ‘Join a network, we’ll do all the work for you.’” For a time, he estimated that 45 percent of the world’s event photos came from WireImage. “The disruption becomes the new establishment, and the establishment is once again attacked, then is hopefully attacked again to become the new establishment,” he said of the sale. “It’s a constant need to go forward by questioning things, it’s a part of the human endeavor.”
This followed film school and a brief career in that industry, undistinguished besides his producer credit on Requiem for a Dream, where he was one of 11 to receive that title—though he didn’t walk away from the experience empty-handed. “It gave me my character,” he said of making independent movies. “It gave me my craziness.” (His favorite he worked on was called Little City—think Friends set in San Francisco but with more sarcasm and Jon Bon Jovi.)
When he looked to his next challenge, art was a likely next step. He had grown up around it. Through his mother, his father had become a major collector, notably of Lee Bontecou and Agnes Martin, so Mr. Simchowitz understood the business.
In that period when Mr. Feuer met him, Mr. Simchowitz spent his time between the coasts. He was close with Jeffrey Deitch and the SoHo gallery Guild & Greyshkul, where he bought so much that, he said, “I basically kept that gallery alive for three years.”
“That’s obviously not true,” said Johannes VanDerBeek, who ran the gallery with his sister, Sara. “Though we did do a lot of business together.”
Art allowed Mr. Simchowitz to become closer with his father. Manfred—or, as everyone including Stefan calls him, Manny—made his money as a corporate raider in the 1980s, then moved to Great Britain in 1986. He sold a controlling 47 percent of his Waicor Holdings group just six weeks before the Johannesburg Securities Exchange crash of September 1987, which was followed by October’s Black Monday. Over Christmas in 1990, while everyone else was away with their families, Manny Simchowitz infamously accumulated shares in the South African media group Perskor in an alleged attempt to “greenmail” them—a raider strategy that involves accumulating enough shares in a company to threaten a hostile takeover, in an attempt to make its owners buy them back from you at a higher price.
Mr. Simchowitz would buy for himself and for his father, artists like Tauba Auerbach and Sterling Ruby. The elder Mr. Simchowitz is said to own the third painting Mr. Ruby ever made, purchased for $30,000. (Mr. Ruby’s work now sells in the high six figures.)
The younger Mr. Simchowitz found he also took to collecting. Soon, he started to make plans for his own biennial in Lisbon, Portugal Arte, the first edition of which debuted in 2010. The 50,000-square-foot show received the standard upbeat event coverage from the likes of Artforum, but after Mr. Simchowitz fell out with his co-organizer and several artists involved in the first show, there was no Portugal Arte 2012.
Mr. VanDerBeek worked on Portugal Arte and said the seeds of today’s Simchowitz were sewn there. Part of the reason why it fell apart, he said, was that Mr. Simchowitz wanted too much from the artists, he wanted not just to show the work but to buy most of it and any other work they had in the studio.
“Right after that, he became a lot more aggressive about finding artists and getting involved with them really early on,” he said.
Because of either his personality or his practices, people began to bristle. Mr. Simchowitz started to want too much art from Mr. Ruby, with whom he had been close and for whom he used to pay production costs, and from dealers, whom he would also reportedly ask for bulk discounts. So began his blacklistings and his weaponization.
Because he exploits the flaws in the system, Mr. Simchowitz is also relegated to its margins, so the efficacy of his strategies is difficult to judge. Mr. Murillo’s quick success probably resulted from his late 2012 show at the Rubell Collection, a bastion of the establishment, more than it did from any of Mr. Simchowitz’s actions. Though, in the margins, he’s also allowed to do anything.
The artist Rachel Lord recently posted a story on Facebook about how Mr. Simchowitz wanted to commission 50 of her “Angry Birds”-themed paintings because he was intrigued, she wrote, by how “awful” they were. He would pay her $5,000, including materials, she wrote, and went on to list his past successes with artists “as if he were a fucking deMedici or had anything to do with it.” After she made a few, she invited him to her studio to see the progress. His response: “can u send pics?” After some back and forth, and the pictures, he wrote back, “i dont want these thanks though.”
One dealer said that Mr. Simchowitz once threatened to sell 10 works by a young artist at auction if the artist left a gallery that Mr. Simchowitz supports. Mr. Simchowitz denied that this ever happened. “Auction houses are not my style,” he said.
Many of his collectors were eager to speak for this article but almost none of the artists with whom he has done business would, including Christian Rosa, the artist for whom Mr. Simchowitz supposedly found a studio and a lawyer, and many asked that their names not appear in the article at all.
“Well, I’m in no way in a bad position, in such a way that things can’t be undone,” Mr. Ito said when asked if he would still work with Mr. Simchowitz if he had to do it all over again. “When you’re young—I’m sorry, I’m still young—when you’re younger and not a lot of people are buying your work, it’s exciting to have someone buy your work.” If he has any regret about working with Mr. Simchowitz, it’s that any press he receives now inevitably includes his former benefactor’s name. “That’s not something they teach you in school; you have to learn about the politics of the art world yourself.”
Mr. Simchowitz still owns about 40 or 50 works by Mr. Ito, and about this the artist doesn’t feel great. “It was kind of manipulative in a certain way but also allowed me to do other things,” he said, though it wasn’t enough to let him quit his day job painting oil derricks.
Mr. Ito said he doesn’t feel the patronage was even anything special, because “he buys everything, and he buys stuff for cheap, so it’s a risk-management thing.”
“I don’t feel like I owe him anything,” he said.
“It is ungrateful,” Mr. Simchowitz said of such reactions and then corrected himself. “It’s not necessarily ungrateful—it’s fearful.” Standard chickenshit—fearful of reprisal from the likes of Jerry Saltz who, Mr. Simchowitz pointed out, was once on a reality television show. What leg does he have to stand on?
“I don’t care,” he said. “I love them, I’ve done business with them. I’ve been there when they can’t sell their art.” His role is to be “the guy on the field you shoot the arrows at and hopefully let everyone else storm the castle.” This, he says, is why he doesn’t want his name on the door at the Depart foundation space. And whether or not the art world ever accepts him, he’s bound to win in the long run. He owns so many pieces by these artists that if any one of them makes it big, so will he.
For the Oscar Murillo opening two weeks ago, David Zwirner opened the doors to the gallery and let the teeming crowd spill to the middle of the street. The conceit had Mr. Murillo recreate a working chocolate factory, similar to the one in his hometown of La Paila, and though the air did smell of chocolate, that whiff was overwhelmed by the dusty Home Depot smell of recent construction. Every 15 minutes or so, assistants wheeled new trash cans filled with ice and beer to a corner near the entrance.
Selling artists before they have fully developed has the added advantage of a lack of critical consensus, though Mr. Murillo’s handful of reviews have not been kind. In the Los Angeles Times, David Pagel called Mr. Murillo’s show at L.A.’s Mistake Room “a Mannerist mess.” Cynics said Zwirner’s high-profile Murillo show was a way to hang a shingle for his valuable paintings that also precluded critics from writing about them. It would be mean-spirited for Roberta Smith to review this conceptual factory departure, even though Mr. Murillo’s signature work is surely in the back room.
Though the opening might have been seen as Mr. Simchowitz’s crowning achievement—the celebration by a blue-chip gallery of an artist that he was among the first to trade—he did not come to New York for the show, because he didn’t want to burden the Mr. Murillo with the associations of his presence.
In a back office, into which Mr. Murillo had ducked because too many people had been asking for his autograph, the artist fidgeted.
“I feel like I’m in a police station or something,” he said after a few questions about Mr. Simchowitz. The two don’t really speak anymore, he said, and yes, he once took him down to Colombia, but then, “I’ll take anyone to Colombia.” He gestured to his factory workers out in the gallery. “I brought 15 people here.”
“We got on as people,” he said. “I think because we’re both outsiders, we both have this hesitation to fit in.”
Correction, 5/17 1 p.m. An earlier version of this story incorrectly stated that Rachel Lord’s last name was “Ward,” and misidentified the artist for whom Mr. Simchowitz once found a dentist.
4 p.m. An earlier version of this story incorrectly stated that Jennifer and Manfred Simchowitz were still married. They are not. It also incorrectly stated the year Oscar Murillo had his show at the Rubell Collection.