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Don Stewart has trained hundreds of riders over his long and storied career—many of whom have gone on to dominate top hunter, jumper, and equitation rings. His longevity in the sport isn’t just about talent; it’s about his ability to evolve without abandoning the values that got him started.
“I think there’s a big difference in how we brought riders up 30 years ago,” Stewart said. “But I’m not here to say one way is better. I think we have to take the best of both.”
It’s this thoughtful mix of tradition and progress that has helped Stewart remain one of the most respected figures in the industry.
The Importance of Barn Rat Mentality
One of the biggest shifts Stewart has seen is in how young riders approach the barn and the sport as a whole.
“We used to be there all day, every day,” he recalled. “We cleaned stalls, we swept aisles, we watched every lesson whether we were riding or not. That’s how we learned.”
That “barn rat” mentality, Stewart believes, created a deeper level of horsemanship. “There’s something to be said for just being in the barn,” he said. “You can learn as much listening to a lesson as you can riding in one.”
Still, he understands that times have changed. “Kids today are busy. They’ve got school, they’ve got other responsibilities. I get it. But I do think we lose something when horses are just another activity on the schedule.”
Adapting the Teaching Style
Despite his legacy in the industry, Stewart is anything but stuck in the past. He’s known for adapting his coaching style to meet the needs of each rider and each generation.
“You can’t teach everyone the same,” he said. “Some riders respond to tough love. Others need you to build them up every single ride. If you don’t adjust, you’re not going to reach them.”
That flexibility has helped him stay relevant through decades of changes in the sport, and it’s one reason why so many young riders gravitate toward him. Whether it’s working on confidence or preparing for equitation finals, Stewart balances accountability with empathy.
“At the end of the day, I want my riders to be tough,” he said. “But I also want them to feel like I’m in their corner.”
Holding the Line on Standards
While Stewart embraces evolution, he’s also not afraid to hold the line on certain standards.
“I still want horses to be turned out well. I still want kids to be polite. I still want them to walk the course and have a plan,” he said. “Those things never go out of style.”
He admits there are moments where he misses the old days. “We didn’t have phones in our hands all day. We talked to each other. We learned by watching. That sense of community in the barn—there’s nothing like it.”
But instead of lamenting what’s changed, Stewart focuses on what he can teach today’s riders through his example. “I don’t expect them to know everything right away. But I expect them to want to learn,” he said.
The Power of Showing Up
One theme Stewart returns to often is the value of consistency. It’s something that’s true whether you’re grooming ponies or jumping in a Grand Prix.
“You can’t shortcut the work,” he said. “The riders who get somewhere are the ones who show up every day and put the time in.”
That work ethic is something he tries to instill in his students, regardless of talent. “I’ve had riders who weren’t the most gifted, but they kept showing up. And you know what? They ended up winning.”
For Stewart, that’s what makes the job rewarding. It’s not just the wins, but the growth. “It’s not about who has the fanciest horse or the biggest budget. It’s who’s willing to get better.”
A Legacy of Balance
In a world that often pushes riders to pick between tradition and innovation, Stewart offers a third option: balance.
“There’s so much we can take from the way things used to be done,” he said. “And there’s so much we can learn from how kids today think and ride. It doesn’t have to be one or the other.”
That approach has helped him shape generations of successful equestrians. But more than that, it’s built a legacy of riders who work hard, think critically, and care deeply about their horses.
“The sport is always going to change,” Stewart said. “But good riding, good horsemanship, good people—those things stay the same.”
To hear more from Don Stewart, listen to episode 320 of The Plaidcast. Subscribe and follow The Plaidcast on your favorite podcast platform for more insight from top voices in the equestrian world.
