Karen O’Connor: Reflections and Regrets of an Eventing Superstar

Karen O’Connor: Reflections and Regrets of an Eventing Superstar

This piece was originally posted on September 9, 2020. 

I have a vivid memory of riding in a clinic at the O’Connor farm in the pastoral hills of Virginia: I’ve finished for the day. My petite, dapple grey horse is settled and I’m filled with satisfaction, relief, and pride for a hard day’s work done. I’m standing on the gentle slope of a hill overlooking a ring where the legendary Karen O’Connor and her magnificent international event horse Biko, are cantering around the corner. Biko is as refined, powerful, self-contained, and charismatic in person as he was in photos. Karen, who was half of his whole, is just as poised.

Then the memory stops, like an old VHS running out of tape. But it was enough that I’ve held on to it all these years. My own piece of this great horse with his great rider who, together, would accomplish so much, but perhaps none more important than the inspiration and passion they gave freely to a whole generation of riders. In the coming years, there would be others Karen rode into our hearts — Prince Panache, Mandiba, Teddy O’Connor, to name a few — but like so many of us, the beginning of Karen’s journey is a familiar one.

To the Limitless Women of Horse Sport

Karen grew up a horse-obsessed kid in Massachusetts. She got her first horse when she was 11 — a not-appropriate, too-big, 16.2-hand horse with “a big jug head” named Midnight. While her mom was out getting her hair done on Fridays, Karen would drag furniture, mops, and brooms out of the kitchen and into the yard to craft jumps. “My mom got home early one day and I got caught red-handed jumping furniture,” Karen says. “One would expect her to react badly but she said, ‘Let’s put the furniture back in kitchen, and it’s time to get you some jumps and an instructor.’” 

Making a Name for Herself 

From there, it was a train that never let up. Karen moved from jumping homemade jumps to riding in the 180-member strong Groton Pony Club. “We were taught by graduate As and active As and it did so much for my riding life.” Soon she got another mount, Erin’s Shamrock, a Connemara cross, who effectively launched Karen’s international eventing career. “He was a beautiful, 15.1-hand small horse. He was a nimble little horse, fast as lightning.” 

Living in New England — the mecca of the eventing world — Karen found her way to Tad Coffin’s program in Hamilton, Massachusetts, the then-headquarters for the U.S. Eventing Team. It was 1977 and Tad had just won individual and team gold at the 1976 Olympic Games in Montreal. But Karen was just hitting her stride, and when Middleburg popped up on her radar, she found her way to Jimmy Wofford’s Virginia farm by way of good friend Bea di Grazia and her mother. “I went to Middleburg in 1977 and never left. I was enthralled by the foothills and the environment and how everyone had some association with horses and realized that that's where I wanted to be. I trained with [Jimmy] for almost 10 years and then I put out my shingle.” 

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At that time, Karen was competing at the advanced level on her gelding, March Brown. She shared the journey of finding him saying, “We were only [in England] for a couple of days and I tried him and loved him. My parents and grandmother joined up and bought him.”  Karen doesn’t take this lightly, recognizing the critical importance of family support and being grateful for it. “Be nice to your parents because they’re your first owner. I take objection to watching teenagers being rude or impatient or short-tempered with their parents when their parents are making that sacrifice.” While not everyone sees their parent’s support for the incredible gift that it is, Karen knows the impact it made on her career and her early success. “My mom and dad were my number one supporters.” 

Aboard March Brown, Karen completed her first Badminton Horse Trials in 1979 at age 21 and finished 10th. “Back then the sport was completely different than it is now. Basically you did dressage so you could get to the jumping phases. There was not a lot of philosophy to the classical training of the horse and rider. In the jumping phases you had to be uber brave and run on down to these jumps that were mostly all fly fences and the combinations were generous compared to the level today. There was very little room for error.”

“When I was in my 20s and 30s there were women who were more successful and who were a little bit older. It was hard to knock on that door. It didn’t open until some other people stepped down,” she says. “There was such a strong tenure of Olympic riders that all had multiple horses year after year, there was little chance for the newbie. That list was Bruce Davidson, Mike Plumb, Jimmy Wofford, Karen Stives, and Torrence Watkins. Those five riders continued to have multiple horses over a long period of time.”  

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It was nearly a decade before Karen made her debut for Team USA. “It wasn’t until I was 30 that I made my first team with Mike Plumb, Jim Wofford, Karen Sizing, and Torrence Watkins. It was not so easy to break into that team.” 

“As a coach and trainer, people gravitate to the tall, good-looking guy with an accent — that’s real. There’s a challenge for an American woman to be successful and to have depth in their business with students. You have to produce results as a coach so people become curious.” 

From there, Karen went on to become the super star everyone knows her to be.  At the 1998 FEI World Equestrian Games in Rome, she won the team bronze medal. In 2003, Karen won individual silver at the Pan American Games. Four years later, she won both team and individual gold at the 2007 Pan American Games aboard her famed mount, Teddy O’Connor. Karen has represented the U.S. in five Olympic Games, winning team silver in 1996 and team bronze in 2000. Karen has also won major events including the Kentucky 3-Day Event, Punchestown, Foxhall, and Fair Hill International (two-times) in addition to countless top-ten finishes in international competitions such as Badminton Horse Trials and Bromont Horse Trials.  

The Challenge for Women

Like all horse sports, men and women in eventing compete against each other, but there is nevertheless difficulty forging a career in the sport as a woman. “As a coach and trainer, people gravitate to the tall, good-looking guy with an accent — that’s real. There’s a challenge for an American woman to be successful and to have depth in their business with students. You have to produce results as a coach so people become curious.” 

But sometimes disadvantage comes hand-in-hand with advantage. “As a woman, you generally aren’t as physically strong [as men], so you can’t use your strength (to communicate with your horse) - you have to use technique. You have to use coordination of multiple aids at one time and that ride offers closer communication with the horse. Women, generally speaking, are softer in handling and talking to horses. We do have that advantage.”  

Yet one thing does affect women and men differently, no matter how equal our horse or skill, childbearing. Karen shares her biggest regret with her husband, the equally prominent eventer David O’Connor: they didn’t have children.

“It’s tragic because we would have loved to have kids, but we were indoctrinated to finish your career before you start a family. I was 35 when I got married and started thinking about having a family when I was 38 or 39, and I went to the doctors and they said you’re not going to be able to do it. That was the first time in my life that someone had said you’re not going to be able to do it,” Karen says.

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“I regret that because time has shown that it is possible to not only have children and go back to eventing but go back to the highest level. The first person who did it was Mary King. And so did Ingrid Klimke and Jessica Phoenix. There’s this babysitting mindset of the entire group of top-level eventers for the children who are following their parents to events. There is a gang of kids growing up and everyone looks after them — it's a collective effort.”

While Karen and David didn’t have a family of their own, they did welcome a litany of young adults into their barn and lives to ride and train with them over the course of their careers. To this day, creating a family atmosphere is a priority.

Karen shares her biggest regret with her husband, the equally prominent eventer David O’Connor: they didn’t have children. “...That was the first time in my life that someone had said you’re not going to be able to do it.” 

“We do have over 100 people that we’ve trained through the years and feel very close to all of them because we had them during that young rider time, and that’s a very formative time of life. When you’re 18 or 19 and you can’t drink and are held back from doing certain things, you test the waters,” Karen says. “It was great to be the parent figure during those times. In most cases it’s tremendously rewarding to influence someone’s life. Many of them started families and now their children are riding.”

Choose the Best, Not the Trendiest

Weighing parenthood and childbearing alongside one’s own natural skillset is important when assessing strategy and potential as well as determining how to make the best of your own goals and riding career. But it’s not the end all be all. Karen speaks from impressive experience when she says, “Surround [yourself] with very best coaching and instruction [you] can find. Not the most trendy.”

It’s not just about who’s a great rider and winning at the upper levels, but also about who’s producing other top riders. “Look for coaches who are producing riders who are winning and riding multiple horses at the highest level. Then you branch out to get your dressage and show jumping experts.” 

Karen underscores that it’s also critical to remember your fitness and balance. “When I was young I galloped race horses for a number of years, which became important for the fitness side of it but also to understand the thinking of a horse that has to go that fast. Get out there and ride some racehorses. Go gallop at the track. Jennie Brannigan is a wonderful example. I remember her as a young rider and know how much her balance has improved. It’s really helpful.”

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As Karen reflects on her monumental career, she acknowledges that success didn’t come overnight. It took years of honing her craft and making difficult decisions to become the rider she is today. 

“There is nothing fast about learning how to ride to the highest level. It’s a dedication to the sport and yet it should never feel like sacrifice. The fact that I could travel the world in the back of a horse trailer has given me the gift of my life. I never went to college since my life was so dedicated to horses. 

“The advice I would give is: education is paramount. College comes at a funny time for riders — it’s at the height of your Young Rider career. Those years of school partially or completely take you away from horses and that’s a big part of your career you’re fearless at 18 or 19. But get that education however you want to get it and absorb yourself into that so you can then use it when you become successful in riding,” Karen says. “There are many people who say you can’t do both, and I know many people who did both and did both successfully because they were determined to get both done. It’s all about determination.” 

“Talent is the last thing on the list of what’s important. If you want to ride at the highest level then the number one thing you have to have is the will to win.”

At the end of the day, Karen calls for some big ideas that are the backbone of being a good rider, not to mention good person. “In a study of the industry I’m a big proponent of embracing being a well-rounded, true horseman. All of the teams have respect for each other but we need to respect everyone. I would advise people to go train with a hunter rider just to open up your mind. Understand the technique in the sport itself. David and I have felt that way right from the beginning. That has been one of the core foundations of our foundation: the mutual respect of all horses of all equestrian sports.”

Finally, it all comes down to the mental game: “Talent is the last thing on the list of what’s important. If you want to ride at the highest level then the number one thing you have to have is the will to win.”

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Feature photo by Shannon Brinkman. 

Written by Courtney Alston

Courtney grew up a stone's throw from Virginia's horse country. What began as a determined love of ponies turned into a devoted competitive spirit as a Young Rider competing in eventing. The rush of eventing has slowly turned into the wows of show jumping and you can now find her astride her Dutch Warmblood mare. Courtney is a mother and wife and lives in North Carolina.