The Art World’s Enfant Terrible Runs for Senate

PASADENA, CA — Stefan Simchowitz, 53, is no one’s idea of a viable candidate, including his own. 

“I have no illusion that I can win or that I stand a chance to win, which is also quite liberating, because I’m not running to win a campaign. I have no prayer,” he tells me. 

Simchowitz, who is running for Senate as a Republican in a seat that has been held by a Democrat for 32 years, is perched at the kitchen island in one of his four homes, an updated Victorian farmhouse on an acre in Pasadena that he’s been building into an exhibition space and artist residency for the past year or so. He calls it Red Barns. 

In a tan Altadena Hardware shirt and one of his signature bucket hats, the contemporary art dealer once dubbed “the Art World’s Patron Satan” offers me sparkling water and a bite of his blueberry muffin. Unlike the Democrats vying for Dianne Feinstein’s open seat—Representatives Katie Porter, who has a $12 million war chest and Adam Schiff ($32 million)—and the Republican front-runner, former L.A. Dodger Steve Garvey, Simchowitz doesn’t seem concerned with shaking hands, kissing babies, or winning votes.

“Sometimes if you know you’re going to lose you can only win,” he says. Stefan sees this campaign as a “vehicle to sell his ideas.” In other words: a performance art project of sorts. How else to make sense of this Democrat-turned-Republican, with no political experience, throwing his hat into the ring? 

This outsider approach has served him well as the enfant terrible of the art world, where he’s circumvented the closed-circuit system of MFA programs, critics, museums, galleries, auction houses, and curators that decide whether an artist is marketable, and for how much. Simchowitz came up by finding starving artists—literally on the brink of starvation, he claims—on Facebook and Instagram, then paying for their studios, materials, and sometimes entire bodies of work outright, before flipping them to buyers, or holding them in his extensive private collection. 

His clientele—which historically includes tech founders who exited their companies and started itching for a Josef Albers; newly flush poker players; and A-list entertainers—trust him implicitly. “He sees opportunities and then he puts a spotlight on them,” Brian Butler, a longtime gallerist in L.A., tells me. “He’s got a tenacity about him.” (Butler himself is voting for Katie Porter, but says he’d vote for Simchowitz “if I was a Republican.”) Though Butler calls Simchowitz a “super mensch,” he conceded he has a “gruff exterior.” 

While his bluntness and allergy to pretension has earned him fans, the management class of the art world scorns him with equal passion. Many collectors, dealers, and artists won’t work with Simchowitz, or anyone who does, arguing that he exploits struggling artists by buying up all their work, then artificially pumping and dumping it. Another L.A. gallerist once called him a “sociopath” and compared him to Charles Manson before walking it back. 

“He sees opportunities and then he puts a spotlight on them,” Brian Butler, a longtime gallerist in L.A., tells me. Stefan Simchowitz (pictured in front of a painting by Zachary Armstrong) owns about 28,000 artworks. (Philip Cheung for The Free Press)

Simchowitz’s approach has also drawn comparisons to Lorenzo de’ Medici, the famous Italian statesman and art patron who funded Michelangelo, and greenmailers, who would buy up enough stock of publicly traded corporations to threaten a hostile takeover in order to get the companies to buy back the shares at a higher price. (Simchowitz’s father, Manny, successfully raided the media company Perskor in 1987). 

Simchowitz says that he’s just rejected the broken old way of doing this and embraced the new.

What’s beyond dispute is that it’s worked. He has 47 employees and owns around 28,000 works spread across multiple warehouses in L.A., two galleries—in West Hollywood and downtown—a print shop, and a new-ish business, Creative Art Partners, that rents out works to high-end hotels, offices, restaurants, and private clients. Then there’s the art playground where we’re sitting. 

I ask him if he thinks the political sphere—where you need mass appeal, votes, sweeping policy prescriptions—is at all like the cloistered and fickle art world. He says yes. 

“It’s a totally political apparatus, constructed in the laws of social contracts that is governed by a very systematic and powerful sort of system. . . ” 

I cut in. “Like a deep state?” 

“I don’t like ‘deep state’ because I don’t like conspiracies.” 

Simchowitz isn’t a very convincing Republican. In fact, he calls himself a “centrist, progressive, on-the-edge-to-Democrat Republican.” He voted for Biden in 2020, but won’t do it again. He doesn’t like any of the Republican nominees, but doesn’t know yet if he’ll vote for Trump. 

What Simchowitz is—like many voters in cities like L.A.—is fed up with progressive politics that, he says, have left the city overrun with crime, homelessness and drug addiction while taxes and housing prices have continued to go up. To steal a phrase from an earlier generation, he’s simply a liberal who’s been mugged by reality. 

In his case, quite literally. Simchowitz says that one of his homes was recently robbed, twice, and that a homeless man used the entry area of one of his galleries as a toilet. He told me it reminds him of his childhood in South Africa. “When you watch a country fall apart, you understand things can actually fall apart. Americans are complacent. They think ‘Oh, we’re fine.’ We’re not fine. We’re in a very dangerous position that needs to be defended,” he says. Simchowitz became a citizen 15 years ago. “It was incredibly emotional because you realize this privilege of being part of a system that has the ability and capital to actually protect and to serve its people.” 

Simchowitz also despises the DEI bureaucracy and social justice politics—he recently pulled his 14-year-old son Morris, who he shares with his partner, the model Rosi Riedl, out of L.A. private school because of it: “He wasn’t learning anything. Every day was a social justice course.” He also hates the vaguely anti-civilization bent of many young progressives. He was recently talking with his niece in Australia, and she was telling him how Alexander the Great was an “evil guy” because he burned down Persepolis, conquering the Persians. “He also founded the Alexandria library, built the lighthouse in Alexandria, pushed civilization forward, codified many things,” points out Simchowitz. “The entire lens of the world for the young is through this morality: rich, poor, colonizer, colonized.” 

Stefan Simchowitz calls himself a “centrist, progressive, on-the-edge-to-Democrat Republican.” (Philip Cheung for The Free Press)

But that’s more or less where the similarities with the GOP end. 

He’s pro-choice: “Women should be pro-choice.” He’s pro–drug legalization: “We wouldn’t have the cartels.” He’s for free healthcare and canceling student debt: “Being buried in debt is a travesty of justice.” He’s also an ardent proponent of modern monetary theory, which holds that the government should be able to print and spend endless money to alleviate unemployment and boost the economy. Other prominent supporters of MMT are AOC and Bernie Sanders, who had as a campaign adviser the professor Stephanie Kelton, MMT’s most famous proponent. 

Simchowitz sums up his worldview under the banner of the New Republican Agenda, or NRA, which he hopes will be a “vehicle in which you rethink your approach to how government works.” So, he suggests, having the government pay Bain to consult on the homelessness crisis. “The federal government has to take back a huge amount of entrepreneurial activity and should utilize the private sector to administer that,” says Simchowitz. He calls the private sector “amazing” and “innovative” and tech, specifically, “incredible” and “world-class.” He says the big, sweeping changes he wants (scaling nuclear energy; full employment) “shouldn’t be done through the federal government doubling its payroll of ineffective employees. It should be done using private sector contracts.” 

“We need a centralized, entrepreneurial government that makes hardcore leadership decisions that are maybe socially unpopular, like rounding up 150,000 homeless people in California and putting them in MASH camps run by the military,” he says. 

Stefan Simchowitz in front of his studio, called Red Barns, by Katrin Terstegen in Pasadena. (Philip Cheung for The Free Press)

We take a tour of his house and the grounds; he ticks off the names of the artists of the works all over. A hanging sculpture made of computer keyboard keys and toothbrush heads by Moffat Takadiwa, a tufted canvas by Gene A’Hern, a Serge Attukwei Clottey portrait, Jasmine Little sculptures. A massive dog, Gray, and a tiny one, Benji, curl around each other on a low couch across from a massive painting—flowers bursting out of a vase—by Georgina Gratrix and under two more colorful works by Serge Attukwei Clottey. 

Simchowitz championed many young, otherwise unconnected black artists from Africa, and resents the art world—always careful to mouth the right platitudes and self-flagellate for their own lack of diversity—for still counting him a villain. 

“I hate the establishment for not being able to see it. I hate the establishment for recognizing people on the boards of museums, who get divorced and get a big settlement,” he says. “Why am I running as a Republican? Because I’ve seen up close the hypocrisy of the left and it’s unfathomable. I really dislike it. It’s one of my core pet peeves.” 

Another reason he says the art world hates him: he’s Jewish. “I speak about money openly in art; I’m the money Jew,” he reflects. “There’s always been this veil of antisemitism that’s invisible.” And then there was October 7, and the veil was lifted. There was the open Artforum letter, published on October 19, that called for Palestinian liberation without condemning the Hamas attacks, and that led to the ouster of the magazine’s editor-in-chief. Pace Gallery, which is owned by Jews, was vandalized. An Ai Weiwei show was canceled in November after he tweeted about Jewish control of finance, culture, and media. 

He got fed up, he says, with people speaking with a “forked tongue.”

“It was time to do something more serious,” Simchowitz says of his decision to run. He announced his candidacy on November 6. 

“Sometimes if you know you’re going to lose you can only win.” Stefan Simchowitz, in front of a painting by Serge Attukwei Clottey and a lamp by Zachary Armstrong, at his home in Pasadena. (Philip Cheung for The Free Press)

Back in the main house, Simchowitz’s executive assistant slash campaign manager, 25, fresh-outta-Brown, valiantly tries to bring the conversation to super PACS, polling, and special interest groups, but Simchowitz wants me to listen to South African jazz from a specific spot on the couch where the airwaves from his silver, state-of-the-art speakers converge perfectly. He plans to incorporate a lot of music into the Red Barns project since “exhibitions are kinda boring.” We sit and listen and he riffs on the creative process and physics before pivoting to Ukraine, the semiconductor war, NATO, and how Obama should’ve spent closer to $4 trillion to get us out of the recession in 2008. “He was too conservative.” 

Eventually, it’s time to go. On my way out Simchowitz hands me a book, The Rise and Fall of the Neoliberal Order by Gary Gerstle. He also admires the scientist Vaclav Smil, the economist Michael Hudson, the Marxist philosopher Guy Debord. As far as politicians, he likes Dean Phillips, and he enjoyed the Reagan book his son got him for Christmas. Trump, like Elon Musk, has energy, he says, “like an armor-piercing bullet.” 

When the polls close, and it’s time to officially fold in the campaign, Simchowitz will likely start a PAC called Simco for America where he’ll pick politicians—like his young artists—who align with his policy goals to donate to. Today, the candidate is off to photograph a show at his gallery, then to his West Hollywood office where he runs his art rental operation. 

Simchowitz is not good at distilling complex concepts. He goes down rabbit holes; he’s sort of fuzzy on the facts. But through some combination of brute force, charisma, coercion, and taste, Simchowitz has been able to push things forward, dragging the elites and the institutions and the artists kicking and screaming behind him. He is not afraid of the internet. He’s willing to talk about how much something is worth and not to be so sanctimonious or academic about it all. He believes in America—at least almost as much as he believes in himself. 

He calls after me as I climb into his assistant’s Tesla. “The platform is ‘Just Simco!’ ” 

Suzy Weiss is a reporter at The Free Press. Read her interview with Jack Sweeney, the college student behind the controversial jet-tracking accounts @ElonJets and @SwiftJetNextDay.

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