The interview takes place in a living room unlike any other I’ve stepped into: part museum, part chaos, wholly Kenny Schachter. It’s his brownstone in New York City, a space saturated with art, color, and contradiction. Zaha Hadid’s sleek furniture, sculptural tables beneath walls teeming with eclectic works. There’s a tension between order and explosion. Through the large window behind him, the backyard, where a life-sized sculpture of Schachter as a T. rex stands among the grass.

“I never wanted to be a lawyer for a second,” he confesses. He initially studied philosophy, but with no interest in a traditional office life, he enrolled in law school mostly to delay the inevitable. “There was no night school,” he laughs, referring to the fake schedule he fed to his employers while he job-hopped through everything from law firms to the stock exchange to fashion. Numbers, he realized quickly, weren’t his thing. Art, however, though deeply personal and unacknowledged, was always lingering in the background.

His first real exposure to the art world came by accident when he wandered into Andy Warhol’s estate sale at Sotheby’s in 1988. It was the moment everything clicked: that art could be bought, sold, and lived with. That revelation pushed him to dive in, no formal plan, no pedigree, just instinct and persistence. He self-taught art history and began creating his own work. He got himself hired to teach at The New School, and he never stopped. Today, he lectures on everything from digital art to the inner workings of the art world. One recent class traced the history of artist-run schools: from Renaissance workshops to Tracey Emin’s art college in the UK. “Art education,” he says, “has always been about doing, not waiting.”

In the early ’90s, Schachter did just that, pioneering pop-up galleries before the term even existed. Back then, they were called “hit-and-run” or “guerrilla” shows, installing art in empty buildings, negotiating leases in exchange for art, and doing everything himself. “I learned how to survive. I cleaned toilets, hung lights, curated and exhibited my work. That’s how I got my education.”

That instinct to create and share outside the system eventually led him to reinvent the concept of the art critic. “When nobody would publish my work, I made my own platform,” he says. “I embedded videos and digital artworks inside my articles. I was doing multimedia writing before anyone cared. It took over a decade before I could even call myself a writer. Schachter’s voice is often raw, always unfiltered has made him one of the most distinctive, and sometimes divisive, figures in art journalism.

“Yeah, people have tried to beat me up in restaurants,” he says casually. “I’ve had to call the FBI. Lawsuits. But I don’t write to hurt. I write because someone has to tell the truth. The art world is addicted to lying. It lies to survive.”

Truth, for Schachter, is less about provocation and more about responsibility. That ethos is perhaps best encapsulated in his recent exhibition, Art in the Age of Robotic Reproduction, where he explores the tensions between technology and tradition.

For Schachter, technology isn’t the enemy. He was among the first to embrace NFTs, giving public lectures, writing detailed how-to guides, and co-authoring a book on the subject. He saw blockchain as a way to bypass the old, exclusionary system of galleries and dealers. But like many things, the potential was quickly swallowed by greed and speculation. “It’s not the tech that failed it’s the people,” he says. Still, he hasn’t lost hope in it entirely. “The system just hasn’t caught up.”

However, his show that used AI and digital media to question authorship and what it means to make art in a world of machines caused controversy. Some critics hated it. One called it the worst show of the year - in March. “I mean,” Schachter deadpans, “at least give the other nine months a chance.” Turns out, the writer had decided the show was garbage before even crossing the gallery threshold. He later admitted it. The show still sold pieces. The work resonated with people. And in Kenny’s world, that’s the only real metric that matters.

Over the years, Schachter’s honesty has come at a cost (of seven figures). One of the most absurd (and painful) examples? His infamous friendship-turned-disaster with disgraced dealer Inigo Philbrick. “Don’t have friends - they’re overrated,” he says, only half-joking. The fallout involved over a million dollars in stolen funds, a friendship shattered, and, even worse for Schachter, a breach of trust with someone he had introduced to Philbrick. Philbrick went on the run to the South Pacific, contacted Schachter under an alias (which didn’t fool him for a second), and then gave post-prison interviews framing his fraud as standard art world behavior. Schachter was not amused. “He learned nothing,” he says. “No remorse, no accountability, just ‘everyone else is doing it.’ Like this is some playground scam and not federal-level fraud.”

Despite the drama, Schachter never lost momentum. If anything, he’s more focused than ever on making art, teaching, and writing without compromise. He prefers not to plan too far ahead. One week it’s a lecture in Basel; the next, a chicken-themed art show in London. After that, a project in Marfa. He doesn't chart a long game. “I’ve never done the same thing twice in two days.” His worldview isn’t built on belief systems. He doesn’t believe in karma, luck, or fate. He reads his horoscope in the New York Post, but that’s about it. He’s a Sagittarius, which fits: restless, intense, often misunderstood. He’s sensitive, too, which surprises some people. But to him, caring and confrontation aren’t mutually exclusive. He sees the art world clearly: “It’s as bad as you think, and as good.” It's exclusionary and hierarchical, yes, but also full of wonder.

Before I leave, I ask what he wants to be remembered for: his art, his writing, his provocations?

“All of it,” he says. “But more than that, I want to be remembered as someone who lived a life that helped others create their own. Someone human. Generous. Real. Not someone who just built their own path but who handed other people shovels.”

Interview and words by Victoria Kulikova, New York City, 2025.’

A special thank you to Kenny Schachter for his candid conversation and solid life advice.