“This new series was kind of this search for the next phase in my painting career,” Windsor says, sitting down on the sofa, straightening his black button-down and readying himself for an articulate explanation of his sudden switch from representational to abstract work.

The man is prepared. He’s meticulous and methodical, too—personality traits that have contributed to a long and successful career as an artist. The North Park alleys Windsor painted for more than 10 years—pretty paintings with lots of lights, shadows and great urban-SoutheCalifornia details like swooping power lines, trash cans and bougainvillea—built him a loyal audience of collectors and appreciators who would’ve been happy to see him go on with the series for a decade more.
“He could have easily gone on with it forever,” says April Game, director of the San Diego Fine Art Society (SDFAS). “His North Park alleys were easy to do, easy to like, easy to buy. But he had reached maturity there, so he was really ready to go beyond it.”
It was Game and SDFAS’s 2-year-old Artist Mentor Program that helped Windsor with the transition, but it was the artist himself who took the first step.
Two years ago, Windsor was wandering through an art museum in Texas. People were gathered around a Rothko painting and, for once, he decided to sit down in front of the painting and figure out what the attraction to abstract art was all about. Windsor is a preparator—one who prepares exhibits for display—and for the decade he’s been working in museums, he’d always just kind of passed by the abstract work.
A year went by before Windsor walked into his North Park studio and started experimenting with abstraction. He painted close-up examinations of cracks and fissures in cement and, eventually, had about 10 pieces piled up. He tucked them away, though, not knowing exactly what to do.
“I was stuck,” he says.
The evolution from figurative to abstraction was an almost predictable and necessary twist in terms of art history.
“When I talk about abstraction in my classes,” explains Alessandra Moctezuma, gallery director and professor of fine art at San Diego Mesa College, “I begin by saying that it was the invention of photos in the 19th century when artists were finally liberated from having to represent the real world and they started to explore other things. So, you began to have the impressionists and the expressionists—the expressionists using more emotions and the impressionists breaking down color and light.”
The transition is an interesting and necessary turn in the careers of individual artists, too. Many abstract or experimental artists who come to mind—Rothko, Jackson Pollock, Pablo Picasso— started with figurative works and slowly found their own styles through experimentation with the fundamentals of art.
“It was obvious there was an interest in abstract, so I pushed Duke toward that,” says Yoram Gil, the mentor and coach in SDFAS’s program. “When he brought in his new paintings, I said, ‘Duke, I don’t get it’—and I really didn’t. I said, ‘You had all this in you. I didn’t teach you any of this. I just asked you to do something and you came up with 20 percent more than I asked you. How come you didn’t go after this before?’ And he looked at me very genuinely and said, ‘I never gave myself permission. You gave me permission.’”
There’s one big North Park alley painting hanging in Windsor’s kitchen. “Wired on Boundary” was the fourth in his series, painted on a 150-thread-count linen sheet he found at a thrift store. It’s one of the biggest he’s ever done, and it’s his favorite. His living room is dominated by his new, textured, deep-red abstract canvasses. He likes to hang them up and look them over for awhile before he decides if they’re done.

We head into Windsor’s studio, where a canvas is primed and ready to be covered in paint and other things he’s started getting into, like sand from a playground, a torn burlap bag or ripped newspaper.
“When I look at this,” he says, picking up a putty knife and a jar of paint, “I already see what I want in terms of texture. This one will probably be closer to what a sidewalk would look like—except in red. Lots of layers, lots of texture—a huge crack right down the third of it and then take it from there. And after that, it’s all on.”
He chuckles and starts in on the canvas.
Windsor (dukewindsor.net) first unveiled his new body of work in September at the Art San Diego: Contemporary Art Fair. As a graduation of sorts from the Mentor Program, SDFAS rented out a room in the Hilton, invited new and old collectors and showed off his latest work in an event called “Launch Pad.”
Newcomers to his work liked what they saw, Game and Gil say, but a lot of his longtime collectors were shocked. Several were even angry.
But a few upset collectors haven’t detoured Windsor from his new path, and the jury’s still out on whether they ever will.

“I’m having a blast for now,” Windsor says. “Yeah, I’m having a blast,” he repeats, as if convincing himself one final time. “What’s interesting about this is that it’s very freeing. As much as I love the alley works, those were restricted to what was recognizable. These are not restricted.
“But the warning I got from Yoram was, ‘You’re moving into something that is foreign to a lot of people…. They’re not seeing what you’re seeing. You’re going to have moments that won’t be pleasing at times, but that’s OK,’” he continues.
“So, I’m having a ball.”
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San Diego Unseen: An Urban Portrait

