Big-boned, hovering near six feet with a shaved-to-the-nubs head, Stefan Simchowitz tromps through the entryway of his home and into the open kitchen. He plucks a bottle of San Pellegrino from the stainless steel fridge, takes a slug, and announces, “It’s been a great day.” Dressed in his usual getup of knee-length shorts, pinkish Nikes, and pricey T-shirt, Simchowitz strolls out the glass-paneled door onto a covered patio draped with bunting cut from the fabric of his favorite designer, Paul Harnden. “I’ve just been kicked out of my first gallery—Blum & Poe,” he says over his shoulder.

Considering that Simchowitz is in the business of buying, selling, financing, and collecting art, this should be somewhat disconcerting. Blum & Poe, after all, is an exceedingly influential modern art purveyor in L.A. “They’re not shlankers,” Simchowitz says. “They’re not rinky-dink.” Getting iced from a source for material should tick him off. But he acts thrilled, describing how he whipped out his Leica and snapped photographs of the banning as Jeff Poe piloted him to the sidewalk. Simchowitz tells me that on a previous occasion Poe slammed him as a “virus to the art world” in front of a few collectors. A couple of weeks from now Simchowitz will insist that I interview Poe for this story. Poe refuses to talk.

Photograph by Gregg Segal

The 44-year-old Simchowitz ranks among the most polarizing people in the L.A. gallery scene. In the past eight or so years, he has earned millions of dollars from art transactions, and his personal collection is worth many millions more. Intentionally bereft of Warhols and Hirsts, it is loaded with paintings by the next generation of auction house darlings—Joe Bradley, Oscar Murillo, and Sterling Ruby among them, all of whom were little known when Simchowitz first purchased their work. He’s sold to marquee names like Steven Tisch, Orlando Bloom, Harvey Weinstein, and Napster cofounder Sean Parker. But he also sells to restaurateurs, professional gamblers, and real estate investors. Simchowitz focuses on small deals, working with emerging artists, and he thrives on conflict. With the eviction, Poe joins a coterie of gallerists who have blackballed him.

When Simchowitz considers those who shun him, he shrugs it off as an “aesthetic choice,” borrowing an existentialist trope about why nations go to war. Simchowitz, whose high hairline and three-day growth of beard recall the actor Jean Reno, often seems on a war footing. He’ll tell you he’s under assault while explaining with a smile how he plays offense. I hear him warn a gallery owner about his “permafrost shit list” and threaten to drive down prices of a certain artist by selling pieces below market value for revenge. “I am amped by vendettas,” he declares, sounding like a character in a James Ellroy novel. “I love to fuck with people who fuck with me. It’s my juice.” And it may well be, but that isn’t why Simchowitz has earned pariah status in particular precincts of New York and L.A.; rather, it’s his wont to ignore unspoken rules that have long dictated the business of art.

In order to keep an artist’s profile ascending, dealers (in other words, gallery owners) believe that prized works must go to “the right” collectors—say the soundtrack composer Dean Valentine or publisher Benedikt Taschen. The collectors then tell their friends, who buy the artist’s work as well. This results in social cachet for the collector and escalating prices for the artist.

“The idea is to distribute art to different people, to get the word out about the artist,” says Joel Mesler, who owns the gallery Untitled, which has branches in L.A. and New York. When I ask whether he would sell to me, however, Mesler replies in the negative and seems to wonder if I have any business writing this story. Simchowitz would happily sell to me, and he likes to buy several pieces at once, which means the gallery owner has little control over how the artist pollinates. Mesler points to Artie Vierkant, a rising sculptor represented by his gallery. “If I sell Stefan five pieces, I will not be able to get the work to other collectors. But I did sell him one of Artie’s.” Mesler sounds surprised when I tell him that Simchowitz got his hands on at least two additional Vierkants. They adorn either side of a fireplace in the Hollywood Hills home of Justin Smith, a professional poker player who’s acquired so much art from Simchowitz that his place resembles a gallery warehouse. Moments before starting a kickboxing lesson in his backyard, Smith tells me that he refers to Simchowitz as his uncle.

Vast sums are earned every day from art, but this is a realm in which commercialism is considered secondary to aesthetics. (Or at least people act that way.) Sculptures and paintings are to be bought and shown off, then sold quietly years later or donated to museums for gargantuan tax write-offs. Simchowitz is not into stewardship. “I usually buy early and sell early,” he will tell you. For this reason many people have derided him as a flipper. It’s a term that causes Simchowitz to bristle, even though he admits to me, “A lot of my clients are flippers. A lot of friends are flippers. A lot of good collectors are flippers. But they hide themselves.”

In the Simchowitz model, money goes into purchasing art rather than paying rent for gallery space. Getting in before artists can begin fetching larger prices, sometimes snagging dozens of their stylistically defining pieces and keeping at least a few for himself, he minimizes risk and gains opportunities to pump up valuations. “I can buy stuff for $5,000 and sell it for $8,000, which is still nothing,” he says, before conceding that the markup (60 percent) is significant. “On a margin basis I charge more than anyone, but people know they’re getting quality stuff, so they don’t ask me questions.” Some of Simchowitz’s clients zip over to his home near the eastern fringe of Beverly Hills to check out paintings and sculptures. Some view them online. Others buy his recommendations sight unseen.

Photograph by Lucien Smith, Untitled (Scrap Metal 4278), 2013

The hard-investment angle has contributed to Simchowitz’s reputation. “Dealers attack me because they think I am some jerk-off hedge fund manager trading art,” says Simchowitz, and he’s right. Gavin Brown, who owns eponymous galleries in New York and L.A., puts it this way: “Buying something in the art world is not like buying a car. According to his reputation, Stefan Simchowitz’s aim is to buy low, sell high, and create opportunities. Then he wants to buy 50 pieces, make himself into a dealer of that artist, and then have a say in what happens with the market. That’s not loving an artist. It’s being a control freak.”

Let’s pretend you are a struggling artist, making sculptures or paintings or whatever it is that your muse inspires you to do. You want an audience, and a gallery can help you find one. But only the most elite among them can catapult you into the stratosphere of six-figure returns. Normally success can take years to happen, if it happens at all, as you bootstrap your way through group shows in Culver City, satellite art fairs in Miami, and dinners alongside collectors who may or may not introduce you to gallery owners with whom they hold sway. It can devolve into a grind. Then along comes Stefan Simchowitz, with plans that could change your life. You have nobody to seriously advise you on what to do, bills have piled up, and he offers to purchase your inventory, advance you money on future work, and connect you to gallery bosses. It can seem like a golden ticket, too good to pass up.

Some characterize Simchowitz as predatory. But if he’s preying on people, they’re people who might otherwise go unnoticed—and they tend to be willing, grateful “victims” at the time. “Stefan looks for a very specific moment, when the artist is not yet with a gallery and his work is not really worth anything yet,” says Mieke Marple, co-owner of Night Gallery downtown. “Stefan knows he will be able to sell the work for ten times what he pays. The artist does not know this, but before Stefan buys the work, it has no value at all.”

So does Marple consider this predatory? “The artist gets exploited early on,” she says, “but Stefan makes a market for him. He buys a lot, but he gets it cheap. There needs to be a certain amount of naïveté or vulnerability for this to happen. For Stefan, it’s mathematical. He buys in bulk, he spreads the wealth, and he only needs to have one [big hit] to pay for everything else.”

Kour Pour is precisely such a find. An interpretive painting of a Persian rug from the British-born Iranian recently sold for $118,750 at auction, but Simchowitz had shown an interest when Pour was unknown. He advised him to stop making small pieces and concentrate instead on larger ones (which, incidentally, can take up to a year to produce). He floated the artist money as well. “When I first met Stefan, he bought and sold what I had been making, funded my studio, and helped me with living costs,” says Pour. People told him to be wary of Simchowitz and his habit of snatching up young artists’ canvases on the cheap, but Pour points out that Simchowitz bought the work before many others wanted it. He got in for cheap only in retrospect; Pour was so unestablished that Simchowitz could have been flushing thousands of dollars down the toilet. That money, in turn, gave the artist room to develop. “He gave me the chance to have a full practice and to focus on my work rather than needing to have a full-time job,” Pour says. “Then after about a year and a half, he brought Joel Mesler to my studio. Joel was there for about ten minutes, on his way to the airport. He told me he thought my work was amazing and said he wanted to give me a show. He wouldn’t have seen my work if Stefan had not made the introduction.”

Other artists feel as though they’ve been played by Simchowitz and want nothing to do with him. Parker Ito, for example, won’t answer Simchowitz’s e-mails. “I made Parker,” he insists. “I advanced him $10,000 at a time and own 35 of his paintings.” When I contact a representative at Ito’s gallery, I’m told that the artist is preparing for his next show and that talking about Simchowitz “brings him down.” Simchowitz doesn’t get it.