Reputations in the art world are forged over many years across countless fairs, openings, reviews

and dinners. Although laypeople may look at a $30 million Richter and compare it to splatters
from a second grader, Richter’s prices are determined not by chance but by the elaborate academic,
journalistic and institutional infrastructure the art world has built to mete out prizes and anoint
the next generation of cultural torchbearers. The collector class has traditionally come from the
very top of the wealth spectrum and has included people looking to trade money for social prestige
by participating in the art world’s stately rituals. Over the last few years, though, a new class of
speculators has emerged with crasser objectives: They are less interested in flying to Basel to
attend a dinner than in riding the economic wave that has caused the market for emerging
contemporary art to surge in the past decade.

Critics charge that Simchowitz often preys on vulnerable young artists without gallery
representation — some say without talent — and buys up huge quantities of their work, then flips
the pieces back and forth at escalating prices among a cultivated group of buyers: a network of
movie stars, professional poker players, orthodontists, nightclub promoters, financiers, football
players and corned-beef magnates, many of whom hold Simchowitz in such high esteem that
they’re willing to purchase the pieces he acquires for them sight unseen, artist unnamed. In March,
in an online screed for New York magazine, the art critic Jerry Saltz tore into Simchowitz with
unusual ferocity, dubbing him a “Sith Lord” and the Pied Piper of the “New Cynicism.”
Simchowitz’s artists may enjoy a temporary surge in prices, his critics argue, but they typically see
little of the upside; in any case, or so the story goes, once their bubbles pop, they’re left for dead.

Many important galleries have blacklisted Simchowitz as a buyer, forcing him to take extreme
measures to secure desired work, including using consultants as undercover mules. Simchowitz
told me about a recent scheme in which he had a consultant buy three pieces from Essex Street, a
Lower East Side gallery. The purchase was nominally on behalf of another client, but the ultimate
recipient was Simchowitz; by the time the gallery suspected the ruse, money had already changed
hands, but the pieces had not been delivered. The gallery requested that Simchowitz not only
cancel the purchase but also return another piece by the same artist that was already in his
possession, which he did. Moreover, the gallerist, furious over what happened, called the other
client to inform him that he was colluding in fraud, an accusation that heartily amused
Simchowitz. (Asked for comment, the gallery responded, “Essex Street has never done business
with Stefan Simchowitz.”)
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To his detractors, Simchowitz is the Michael Milken of the art world — someone who has created,
through his extensive network and force of personality, a market for high-risk, high-yield
investments that have little to do with the fundamentals of talent and critical acclaim. By contrast,
Simchowitz sees himself as something akin to the art world’s Mark Zuckerberg, a 21st-century
player using technology to disrupt the institutional establishment. Despite his reputation for
transaction-driven opportunism, Simchowitz insists he is playing the long game. “I’m looking for
the big fish,” he told me, predicting that in 30 years his investments in the next generation of art
stars could yield him a fortune worth a hundred million dollars. “The downside is that it’s worth
only $50 million,” he allowed. “But I want the big kahuna.”
Simchowitz is in no immediate danger of amassing such a fortune. He lives in a modest one-
story home on the southeastern precipice of Beverly Hills, a region that real estate agents
optimistically call “Beverly Hills adjacent.” When accused of greed, he’s fond of reciting the value
of his home — $1.2 million — as proof of frugality, though he also rents an additional house across
the street, co-owns two homes in Australia and until recently maintained a residence in SoHo
before deciding that it was “cheaper to stay in hotels.”

The son of the South African industrialist and Clint Eastwood look-alike Manfred Simchowitz — “a
gangster,” as his son admiringly describes him — Simchowitz was born in Johannesburg but sent
away to a boarding school in England at 6. He came back to South Africa for middle school, only to
endure severe bullying at his Jewish day school, where a group of boys twisted his ankle so severely
that it fractured in four places; after the incident, he left South Africa to study karate in Japan. He
finished his secondary education at boarding school in the United States and ultimately graduated
from Stanford in 1992. After college, Simchowitz tried his hand at the movie business, unprofitably
producing 13 independent films between 1996 and 2006 (his best-known film, “Requiem for a
Dream,” netted him only $12,000). From Hollywood, he branched into the tech sector, co-
founding a celebrity photo and video service that eventually sold to Getty Images in 2007 for $200
million (Simchowitz says that his cut, diluted following the dot-com crash, was only 2 percent).