In 1970, the sculptor turned architect James Wines, then 38 years old, agreed to design the sort of building no self-respecting artiste would usually touch: a suburban big-box store. Wines, who was friends with artists such as Cy Twombly and Robert Rauschenberg, had devoted years to welding steel and concrete into abstract sculptures. He had exhibited with prominent galleries, including Marlborough, won a Guggenheim Fellowship, and seen his sculptures installed on university campuses. The owners of Best, a since-closed chain of stores, tried to commission him to make art for the outside of their all-you-can-buy shopping centers. Wines refused. Those plopped-down sculptures—“turds in the plaza,” he now calls them—were old-fashioned and irrelevant. His counter-offer: Why not make the buildings the artwork instead?

The result was nine big-box stores that looked like Walmarts in the midst of a nervous breakdown—corners ripped off, bricks tumbling down from the façade. They launched the now 91-year-old Wines’s ongoing crusade to blur the boundaries between art, architecture, and public space.

“I really like to look at [art] and think, Oh my God, how’d they ever think of that?”

“Starchitects” such as Frank Gehry and Rem Koolhaas assert themselves with big glittering structures that are obedient to the rules of good taste. Wines’s designs, which range from fast-food restaurants and public parks to Off-White stores in Asia, have made him the ultimate “anarchitect”: an anarchic architect who rejects the self-seriousness of design and pokes polite society in the eye. See his Floating McDonald’s, built in 1983 in suburban Illinois. Since remodeled, the original restaurant appeared to be in the midst of obliteration. Its roof seemed to levitate, and the walls hovered above the building’s foundation, revealing diners’ feet and ankles to people outside.

When Wines’s Best stores opened across the country, in cities from Sacramento to Miami, people wrote angry letters complaining about the unorthodox designs. This thrilled Wines and the stores’ owners. Someone who complains “has done something very unusual in the course of his day,” Sydney Lewis, Best’s co-founder, said in an interview. “He’s thought about architecture.” (The stores have since been remodeled or destroyed.)

In 1983, Wines’s Floating McDonald’s opened in Berwyn, Illinois.

On a recent blustery Monday afternoon, Wines, who’s lived in New York City long enough to have helped gentrify SoHo, made his inaugural trip to Hudson Yards, the $25 billion collection of super-talls overlooking the Hudson River, in Midtown. Built in 2019, Hudson Yards, according to its own Web site, is not only a giant office park and mall but also “a must-see stop for the culturati” that “was built—and continues to be curated—with art lovers in mind.” Wines wanted to scope out the “new version of what they consider public art.”

Why not make the buildings the artwork instead?

Wines, who grew up in Oak Park, Illinois, and studied fine art at Syracuse University, was living on Greene Street in the late 1960s when he decided to help art escape the sterile preciousness of galleries. In 1970, he and several collaborators established the architecture studio SITE (Sculpture in the Environment) to create structures that lived along freeways and in strip malls—and, as Wines sees it, were themselves art. Some critics dismissed his work as overly commercial; others brushed it away as jokes. Eventually, his influence became undeniable. In 2013, the Smithsonian honored him with a lifetime-achievement award.

The Ghost Parking Lot at the National Shopping Centers, in Hamden, Connecticut, 1977.

For our tour of Hudson Yards, we started at a shiny Starbucks at the foot of the Vessel, Thomas Heatherwick’s 16-story steel staircase that resembles a wasp’s nest. Wines didn’t want to talk about it—Heatherwick is a friend—but allowed that it was “not one of his finest moments.” He motored his wheelchair toward outdoor sculptures made by Sui Park.

“James, stop!,” Wines’s partner, Kriz Wines, shouted as he zipped his wheelchair past the sculptures. “James! Look left! Right here! Art! ART!”

Wines contemplated Park’s clusters of colorful cones woven out of zip ties. They weren’t turds in the plaza, he conceded, but Park “wanted to make those shapes, and she put them there.” Wines has spent decades urging artists to make pieces that wouldn’t sit in an environment but could be interpreted as the environment. “So much public art is almost indifferent,” he said. “It’s like a chunk of old-fashioned abstract art that has just been randomly installed by whatever committee decided to do it.”

Spotting an intriguing piece, Wines cruised excitedly toward it. “Ah! It’s a streetlight,” he corrected himself.

The Vessel, Thomas Heatherwick’s 16-story staircase in Hudson Yards. “Not one of his finest moments,” says Wines.

Next, he ventured into the lobby of 50 Hudson Yards, an office tower that’s home to BlackRock and Meta, where two sculptures by Frank Stella, another friend of his, were on display. One, nearly two stories high, consists of a pair of enormous silver metal stars balanced on a mirrored pedestal. The other features colorful geometric shapes juxtaposed with white metal swirls inspired by cigar smoke, explained a security guard. Wines stared impassively at the stars. “I’ve seen this thousands of times, this exact sensibility and everything,” he said. “I really like my mind changed. I really like to look at it and think, Oh my God, how’d they ever think of that?

Wines’s own approach to public art is best summarized by the Ghost Parking Lot, an installation built in 1977 for which Wines paved over 20 cars in an otherwise totally normal Connecticut parking lot, leaving only the automobiles’ bumpy black outlines. Whereas most public art is like jewelry on otherwise bland buildings, the Ghost Parking Lot is closer to a prosthetic limb, fusing with its host. “You couldn’t move it to a museum without a total loss of meaning. It had to be in the public domain,” said Wines. Meanwhile, Stella’s stars “could be anywhere. You could take this and move it outside; it would be just as relevant.”

A Hudson Yards employee in a blazer approached us. “Hi, I’m Janice, the brand ambassador. Could you move that way?” she asked, pointing us away from the building’s entrance. Looking at the art in Hudson Yards was considered an impediment to the flow of nonexistent foot traffic.

We continued to the mall, where Wines delighted in the white waves on the outside of the Louis Vuitton store. “A nice wriggly wall!” he said admiringly. “Psychologically—that’s curious. That must be an interesting store.”

On the second floor of the shopping center, Wines gazed out the window at Hudson Yards’ nest of skyscrapers. To him, buildings are the ultimate public art, and as artworks, they can—and should—communicate. He reminisced about his travels in Italy, visiting Renaissance cathedrals from an era when buildings still fused messages with structures. “I talked to the buildings, and the buildings talked to me,” said Wines. He looked at an expanse of glass high-rises that seemed ripped from a generic digital rendering of a city. “A façade like that doesn’t tell you anything except it’s an enclosure.”

Bianca Bosker is the author of Get the Picture and Cork Dork. She’s a contributing writer for The Atlantic and has written for The New Yorker, The New York Times, and The Wall Street Journal