Cowboys & Indians Magazine
by Michele Powers Glaze
First and foremost, artist Jeremy Winborg is a family man. The married father of five even runs his art business as a family affair. Never was this more evident than at The Russell auction last year when the first-time entrant’s work generated a pre-auction buzz.
The painting of Jeremy Winborg’s 13-year-old Navajo niece and frequent model, Layla, defiantly holding a rifle had caused a family disagreement five months earlier when it was submitted for consideration. His wife, Danielle — who regularly titles the paintings, helps find models, and runs the website — wanted to call it Little Ass-Kicker. A great title, Winborg agreed, but concerned it might be a little too much, he settled instead on High Caliber. When Winborg learned of the excitement surrounding his painting, he became convinced his wife had been right all along and the young couple spent the day of the auction running around town searching for the auctioneer to change the title — but to no avail. Disappointed, they headed back to their hotel to dress for the evening’s event. On the way into the lobby, they recognized people from the auction and told them their tale of frustration. One of the folks was the auctioneer’s son, who promised to get word of the name change to his father.
At the auction that evening, the Winborgs waited for their painting to come up on the auction block. As time ticked by, their 18-month-old daughter became more and more restless. When the auctioneer finally appeared with the painting, he said, “Well, I heard through the grapevine there’s been a name change here. Instead of High Caliber, the name’s Little Ass-Kicker.” The crowd went crazy, laughing and clapping. Even so, the artist was ready to take his squirming toddler back to the hotel until bids hit $17,000, $18,000; then three or four people got into a bidding war that ended with the painting going for $52,250. The night became one of the highlights of Winborg’s career.
When the auctioneer finally appeared with the painting, he said, “Well, I heard through the grapevine there’s been a name change here. Instead of High Caliber, the name’s Little Ass-Kicker.” The crowd went crazy, laughing and clapping.

Little Ass-Kicker.
C&I caught up with Winborg at his home in Cache Valley, Utah, to talk about his art.
Cowboys & Indians: When and how did you begin to paint?
Jeremy Winborg: Being around my dad’s studio as a little kid. [When] I was probably 3 years old, I remember my dad let me paint a stroke on one of his commission paintings. That really stood out to me. After that I had no other plans besides to be an artist. I never explored other options, and I’m really happy I didn’t. This is a great profession for me. I really enjoy it.
C&I: What was your artistic training?
Winborg: I focused on artwork all through high school. It was the only thing I cared about and my grades probably reflected that, too. But I did spend a lot of time working on my paintings, and I was actually able to do that as a profession throughout high school.
I did go to Utah State and majored in art. But I really believe I was fortunate enough to receive the one-on-one training that most aspiring artists never get: getting to work with my dad, seeing how the business really works, learning how to stretch canvases, how to sell artwork, how to meet deadlines. Utah State was great, for sure, but working in the studio with my dad was the most beneficial to me.
C&I: How did you develop into your current style?
Winborg: When I was in school I was more abstract, wild, loose with my paintings. After I got married and started having kids, my style tightened up and I got more realistic so I could sell more. Through my 20s and into my 30s, I painted landscapes and some religious pieces, but I’ve always wanted to paint figures. In my early 20s, I talked with the owner of a prestigious gallery and said I wanted to be a figurative artist. He told me that was the worst decision I could make — nobody wants to buy figurative art. So for the next 10 years ... I painted landscapes. About eight or nine years ago, on a whim, I hired my niece, who’s a Navajo, to model for me, and we got some authentic Native clothing and had a photo shoot, [and] I painted her. I love painting Native Americans. From there, I added the abstract backgrounds.

A Storm on the Horizon.
C&I: Your niece seems to be your primary model. What is there about her that you find so compelling?
Winborg: First off, she is just such a cute little girl. She’s really photogenic and she’s a great model. Over the years we’ve done enough photo shoots that she knows exactly what I want. So when I hire her, she gives me fantastic photographs. ... I’ve branched out, and I’ve got four young girls modeling for me now. Two are excellent. I’ve got a photo shoot coming up in the next couple weeks with a few girls in their mid-20s who are going to model for me, and both are really excellent. I’m starting to expand out now that I’m selling more. I’m looking desperately for a 5- or 6-year-old girl who is willing to come down and model for me, too. I’d love to find an older woman who would model for me. I actually have a photo shoot coming up with this older lady coming to visit her family. I think she’s in her 60s or 70s. She has the long gray hair with braids. Hopefully, that pans out.
C&I: How do you research and procure the Native clothing and artifacts you use?
Winborg: I do a lot of reading — online research — and I have a great resource for authentic museum-quality Native American clothing living in this valley I’m able to work with. They rent me the clothing for the photo shoots; they’re also a great resource for information.
C&I: Your subjects are predominantly female. Is that deliberate?
Winborg: I gear most of my paintings toward females, Native American women, and little girls. Maybe that’s the case because in reading their history, it’s really interesting how integral a part of the tribe the little girls and women were and how much they did to contribute to it. I grew up with three sisters, and having four daughters myself, perhaps I have always been drawn toward portraying females. They’re more interesting to me, I guess.

Maiden in Repose.
C&I: Your dad was instrumental in your becoming an artist and you still work with him. Winborg: I actually work and share a studio space with my dad, who has been an artist-illustrator for 40 years. His studio space is next to his house, and I live about two blocks from him. I can ride my bike or walk to work, and the kids can come up to the studio to paint so it’s a good setup. It’s 30 by 50 feet and has hardwood flooring from an old school we spent three years scraping by hand. We’re up on the East Bench with an awesome view of the valley, which actually has been the background of some of my paintings. I’ve been fortunate enough my entire life to have my dad working in the same studio, so we can bounce ideas off each other. If I’ve been working on a painting for a week straight, there might be a huge mistake or something that’s not right that I might not even be able to see unless I put it away and forget about it for a while. Being in the same studio space with my dad, he can come over and point something out that I would not have even noticed before I sent the painting out.
C&I: You have a big following. What do you think people are connecting with in your work?
Winborg: The feedback I get from my artwork is that people are really drawn into the expressions on the faces of the models ... plus the fact that I do traditional paintings with modern, contemporary backgrounds. I sell many paintings for second homes and cabins, but I also sell to people who would never buy Western art, people who have more modern homes. They love the contemporary feel of my work. I think my work bridges the gap between Western art and contemporary.