Darragh Kenny: His Roots, His Rise, and His Ongoing Mission

PHOTOS BY George Kamper

A BEHIND-THE-SCENES LOOK AT THE OLYMPIC SHOW JUMPER—HIS ROOTS, RISE TO THE TOP, AND HIS ONGOING MISSION TO DEVELOP THE NEXT GENERATION OF EQUESTRIAN STARS.

Irish Olympian Darragh Kenny has spent a lifetime in the saddle. Raised in Offaly, Ireland, by parents who bred and trained horses, Kenny was immersed in the sport from the start. His rise through the show jumping ranks can be attributed to grit, passion, and an unwavering love for the horse—all qualities that continue to shape his career today. From his early days riding ponies in Ireland to the Olympic arena, founder of Oakland Stables and a mentor to the next generation, Kenny reflects on the journey that brought him here—and where he hopes to go next.

EARLY CAREER AND RISE TO THE TOP

For Darragh Kenny, horses weren’t just a childhood hobby—they were a way of life. Exposed to his parents’ breeding and training operation at a young age, it instilled in him what it meant to dedicate yourself entirely to the sport. “From the time I was born, I was surrounded by horses,” he says. “When we got up in the morning and looked out the window, there were horses in the field.”

Darragh’s early exposure to horses and natural talent led to a rapid rise through the ranks. He began riding ponies and entered his first grand prix at just 14. A pivotal moment came when he won a training bursary to spend two weeks at North Run Farm in the U.S. with Missy Clark and her husband, John Brennan, who is originally from Ireland. The opportunity came at the perfect moment—at age 20, Darragh realized he needed to leave Ireland to reach the top of the sport. That short visit turned into a lasting partnership. Within a year, he was competing in Nations Cups and World Cup Finals. “These are things that I had completely dreamed about doing at some point in my life, never mind at 20,” he recalls. Darragh credits much of his success to their mentorship: “Missy and John gave me huge opportunities. Without them and their support, I would not have gotten to this level.”

HIGH-STAKES COMPETITION AND OAKLAND STABLES 

Above: Darragh riding Eddy Blue, owned by Carol Sollak, for the EQ Living photoshoot. 

In 2009, during his first year with North Run, Darragh won the World Cup Qualifier CSI4* in Syracuse, N.Y.—a breakthrough that set the tone for his future success. “This was a turning point in my career,” he reflects. “It gave Missy and John the confidence in me to push me to do more, and it opened doors for me.” 

By 2012, at just 24, Darragh launched Oakland Stables. While the vision was still evolving, his goals were clear: to compete at the highest level, mentor young riders, and build something enduring. Since then, he’s become a consistent force on the international stage, earning top placings and victories in some of the world’s most prestigious grand prix competitions, both individually and as a member of Team Ireland. His resume includes standout performances at the 2014 World Equestrian Games, multiple Nations Cups, the Longines Global Champions Tour, the League of Nations, and major grand prix events across North America, including Spruce Meadows and the Winter Equestrian Festival. 

At 27, he helped Team Ireland win the coveted Aga Khan Trophy at the Dublin Nations Cup—an especially personal milestone. “Every kid riding in Ireland, that’s their dream. So to be able to do that at quite a young age was a massive turning point,” notes Darragh. He went on to help Ireland qualify for the 2020 Tokyo Olympics and was named reserve rider for the 2024 Paris Olympic Games. Representing his country holds unmatched significance. “Winning grand prix events is great, but winning with a team—like at the Nations Cup or Major League—there’s more emotion, more intensity. I love that part of the sport.” 

Today, Oakland Stables operates as one of the top training and sales programs in the U.S., with dual bases in Wellington, Florida, and at the historic Ox Ridge Hunt Club in Darien, Connecticut. Darragh had long admired the facility and the area, and when the chance to partner with Ox Ridge arose, it felt serendipitous. “Everything happens for a reason, and that seems to be something that was supposed to happen—and I love being there,” Darragh admits. 

The program has evolved into what Darragh calls a “brilliantly functioning machine,” with eight trainers and more than 30 staff supporting riders from beginner to international five-star level. “I always thought Ox Ridge deserved to be recognized as a high-sport, high-level facility, but I didn’t want to move away from what its grounding was and what started it,” he says. 

 Above Left: Carmen Barrera, Darragh’s loyal assistant and manager, who has worked with him for 10 years. Above Right: Oakland Stables, Darragh’s Wellington base. 

Darragh values the bonds he forms with his horses, crediting several with shaping his career. Obelix, who carried him to his first World Cup qualifier win, marked a turning point. VDL Cartello left a lasting impression as his Olympic mount, while Eddy Blue, a current star, is, in Darragh’s words, “one of the most special horses I’ve ever ridden.” Their partnership, however, wasn’t instant. While Darragh clicks quickly with most horses, it took him nearly nine months to figure out Eddy. “To struggle at the start, and for it to be as hard as it was, was probably a great thing in the end,” Darragh reflects. “We learned a lot about each other very early on, and now it really pays off.” 

BEHIND THE SCENES 

Darragh is quick to credit the people behind his success—his team, his horses, and the entire operation at Oakland Stables. “I’m very lucky. Many of my people have been with me seven, eight, even twelve years. You can’t do this without that kind of loyalty and trust.” He emphasizes the importance of surrounding yourself with people you and your horses can depend on, noting that trust and loyalty are essential to success in show jumping. 

Left: Darragh is very thankful to have great owners: Carol Sollak, HKC collection, Vlock Show Stables, and Andrzej Oplatek. 

“With leadership comes responsibility,” he adds. “I try to be the kind of boss I would want if I were working for someone else. People need time off; they need respect. And when they care as much as I do—sometimes even more—you need to recognize and respect that, because without them, we wouldn’t be here.” 

His passion for horses is ever-present, even in quieter moments. “Even during downtime, I still ride every day. It’s just less pressure and more about enjoying the horses,” he says. In the lead-up to major competitions, his focus shifts entirely to the horses competing, ensuring they feel their best. 

The 2020 Tokyo Olympics marked a turning point in how he approaches his career. Team Ireland didn’t achieve the results they had hoped for, and the emotional weight of that moment hit hard. “Afterwards, I took time off to reflect. It made me realize the importance of balance—life can’t be 52 shows in 52 weeks,” Darragh says. “You have to have a life outside the ring.” Since then, he’s embraced a slower pace when needed—for himself, the horses, and his staff. Outside the ring, Darragh enjoys traveling and unwinding with great food and a quieter mindset. 

Above: Darragh aboard Chic Chic, owned by Vlock Show Stables, at the Dublin Horse Show in 2024. Chic Chic is retired from show jumping and is now a top breeding stallion. 

LOOKING AHEAD 

After a successful European championship, finishing 7th overall, Darragh is now focused on the 2026 World Cup Finals in Fort Worth, Texas, and the 2026 World Cup Finals in Aachen. Darragh remains determined to continue his success with his current string of horses. He finds great pleasure in training up-and-coming grand prix athletes like Mimi Gochman and Elena Haas.* His ambitions extend beyond personal accolades. “If I could compete at the World Cup Finals alongside Elena and Mimi, that would be really meaningful.” 

His long-term goals include the 2028 LA Olympics and helping Ireland continue its ascent on the global stage. Yet legacy, for Kenny, is about more than medals. 

“Everybody deserves a chance. I was lucky that people helped me along the way, and now I want to help the next generation. That’s why I took over Ox Ridge—so I could build something that lasts and guides young riders through the sport the right way.” 

As both a top-level rider and mentor, Darragh Kenny continues to lead by example committed, grounded, and driven by a love for the sport that’s as strong now as it was when he was a child peering out the window at ponies in the field.

To view the digital magazine version of Darragh’s story, click here. To read more of EQ Living’s featured equestrians, click here.