Recalling his childhood in Johannesburg, Simchowitz says, “I was a shit talker like I am today, and I got severely bullied.” The worst beating, he claims, resulted in his leg getting broken in four places. Afterward Simchowitz nurtured a martial arts obsession that effectively ended the abuse and only stoked his confidence further. In 1996, he met Riedl on the beach in Malibu and seemed oblivious to the fact that, objectively speaking, she should have been wildly out of his league. “Rosi gave me her number,” he remembers. “A week later we moved in together.” Five years after that, the couple left L.A. to live in TriBeCa, where he co-managed investments for a wealthy family.
Riedl and Simchowitz split up in New York around 2004, but before they reunited, Simchowitz employed his bravado to best effect in Manhattan. “I saw Stefan across the room and thought he was extraordinarily handsome,” remembers Cesarina Ferro, a fashion model at the time who now works in the art business, sometimes with Simchowitz. “I was a beautiful girl who could have gotten anything, and I went up to him. I was attracted to him. Most women are, and he always has a hook. He met Rosi and showed her pictures of Australia. He pulled me in a certain way. He does it with all women, and it’s always something that he will never do again. I saw him wash a dog with a young model. He’ll never do that again.”
Simchowitz seems to have an instinct for pinpointing what people want. Dealers get a man who’s willing to purchase the least sellable item in the gallery. Artists get a booster with financial support to dole out. (When we are in the Alhambra studio of Marc Horowitz, Simchowitz points to dozens of paint sticks and racks of spray paint. “You think that’s cheap?” he asks. “It’s $4,000 right there, and I paid for it.”) Collectors gain access not only to new pieces by overlooked and anonymous strivers but to offerings that galleries won’t necessarily share with them.
As my time in L.A. winds down, I meet a local art buyer with oversize sunglasses, a bit of scruff, and tightly tailored jeans in Simchowitz’s backyard. Insisting that I not use his name, he tells me about a friend. “He said to me, ‘I’m not going to buy anything from that guy Simchowitz. He’s bad.’ Then I brought him over to meet Stefan,” the buyer recounts, slipping his feet in and out of ankle-high boots as dusk encroaches. “After we left, he asked me what Stefan can get him. Initially a lot of these rich collectors get pissed off at Stefan. They’re used to getting special access to galleries. But Stefan is a lot more democratic, and these guys don’t like that. They also don’t like paying extra to get an artist. But I gladly pay a couple grand more to know that I am free with the art and will not get a hard time for selling it when I feel like selling it. There is a set idea of how things should be transacted. When you go against that idea, it rattles them.”
Simchowitz beams at the depiction. He later tells me, “So many of the new collectors are locked out of the gallery scene. They have been told that they can’t get a good seat in the club. I opened up a new club across the street, and some people are moving over to me. I am creating new collectors. Traditional dealers get scared when they see that.”
Even those who hate Simchowitz admit that he has a knack for spotting talent. He trolls Instagram, speeds through unsolicited e-mails, and checks out shows at small galleries. He says he’s currently backing nearly ten artists, including L.A.-based digital painter Petra Cortright. “I got her a great dealer in New York,” says Simchowitz. “She will be huge.”
To help prime the market, Simchowitz might post something for his Facebook or Instagram followers to see, flogging his image as an early investor in the current crop of raging modern art stars. “I saw Oscar Murillo’s work and said, ‘Give me as much of that as you fucking can’ ”—he claims to have 34 pieces by the South American. “People laughed at me, but I knew he would be huge. Sterling Ruby was selling works on paper for $8,000; I looked and was, like, ‘Holy fuck, this guy is a great artist.’ From that day on I bought everything I could afford. He ended up being huge. I saw Joe Bradleys and bought them for $4,000. I said that he is the best painter in America. Now he is huge.”
That “huge” is a huge part of the Simchowitz vocabulary makes sense: He’s in the business of generating demand, but he’s also an outsider pushing toward the center. As he puts it, “Even dim stars add light to the universe.” Whether in person or online, he conscientiously exhibits erudition. He quotes Duchamp and plays YouTube videos by economists. One afternoon in his living room, Simchowitz gestures toward stacks of books on art theory and politics. “It doesn’t seem like I read that shit,” he says. “But I do—and I am not a polite academic.”
In an apparent gambit for acceptance, he has teamed with Pierpaolo Barzan, an Italian art collector and industrialist who founded the Depart Foundation, a Rome-based nonprofit that presents the work of emerging as well as midcareer artists. Barzan relocated his family here last year and launched an L.A. branch of the foundation, with Simchowitz contributing funds and providing input. Not a gallery—the works aren’t for sale—Depart L.A. occupies a cavernous, beautifully lit space near Gil Turner’s wine and spirits shop on Sunset. But it does enable Simchowitz to help bring attention to artists he believes in, which is to say, artists he trades in. It’s also a way to show off his taste.
On opening night last fall the venue is given over to the American debut of an Italian artist named Gabriele De Santis. Painters, collectors, gallery owners, and journalists circulate through the former massage center, taking in tropically hued canvases with black hashtags and exclamation points. Wearing an outrageous Harnden outfit—Bermuda shorts, a billowing, candy-colored shirt, and brown wingtips—Simchowitz schmoozes, doles out hugs, and snaps photos.
Later the party moves to Barzan’s minimalist home in the Hollywood Hills, where a professional sports bettor offers actor-comedian Andy Milonakis $1,000 to jump into the swimming pool with his clothes on. It proves to be an easy grand. Watching Simchowitz flirt with a brunet, you’d never know he is pissed at De Santis, who had suggested that they keep a distance from each other in case potential curators might consider them tightly aligned. De Santis should have been grateful for the help in being introduced to L.A., Simchowitz says. “Artists are utterly disloyal, greedy people,” he fumes. “They’re quite consistent.”
Early the next morning he’s still griping more about De Santis as we drive again to Paper or Plastik for caffeine. Then, after wondering aloud how to lure the high-rolling sports bettor, Simchowitz ferries over cups of coffee and one-eighties to an impending conquest. “Everybody keeps asking who will be the next Oscar Murillo,” he says. “Now I know. I discovered him on the Internet. He’s an African artist named Ibrahim Mahama. He will be massive and will congeal my eye. I’ve sold Ibrahim’s work to ten of my best collectors without telling them what they will be getting. I called it the Simchowitz Trust-Me Special. He is going to be huge.”
Simchowitz leans close, making it easy to forget that in his world, everybody he supports is going to be huge. Then he adds, “After this, nobody will be able to say anything about me.”
Michael Kaplan is a freelance writer based in Brooklyn. He has written for Details, Playboy, and Wired.
This feature appears in the March 2015 issue of Los Angeles magazine.