Thursday, Jul. 3, 2025

Jan Byyny Thompson Has Proven That She Belongs At Rolex

Jan Byyny Thompson vividly remembers her first time riding in the Rolex Kentucky CCI****. In 2003, she tackled her first four-star there on Shared Dreams, or "Whitey," a gray Thoroughbred who many had believed just might not be up to the task.

"When we got there, not only was Whitey wild, but I could hardly ride him. I was in tears by the second day," recalled Thompson, 38.
PUBLISHED
WORDS BY

ADVERTISEMENT

Jan Byyny Thompson vividly remembers her first time riding in the Rolex Kentucky CCI****. In 2003, she tackled her first four-star there on Shared Dreams, or “Whitey,” a gray Thoroughbred who many had believed just might not be up to the task.

“When we got there, not only was Whitey wild, but I could hardly ride him. I was in tears by the second day,” recalled Thompson, 38.

“I think Whitey knew he was somewhere serious as well. I was watching all these people riding around, and they all looked so fancy, and their horses were going so well, and there I was, rocketing all over the place. I thought to myself, ‘What am I doing here?’ “

Her nerves didn’t abate much upon walking the cross-country course.

“Then Phillip [Dutton] walked the cross-country course with me three times. At one point, I asked him, ‘So you really think I can do this?’ Because he kept saying ‘You get to here, you start kicking now.’ Phillip is so relaxed and a man of so few words, just the fact that he walked the course with me three times and told me to kick, I knew this was serious,” she said.

But she and Whitey galloped to 10th place in their first four star together and proved they belonged there. “It was great–better than I expected. He was super on cross-country. I went the long way at the coffin, but everywhere else, he jumped right around. He didn’t have any bother about it whatsoever,” she said.

“I think that there were a lot of people who were thinking that there was no way that Whitey was actually going to jump around a four-star for me,” she said. But the stellar freshman performance put paid to a lot of naysayers about Whitey’s abilities.

This year, however, Thompson is aiming for Rolex Kentucky with two very legitimate contenders, Task Force and Waterfront, and she’s on the USEF long list for the World Equestrian Games. In just three years, she’s come a long way from feeling out of place at Rolex.


One Of The Most Unlikely Horses
Whitey’s 2003 Rolex performance put Thompson onto the map in upper-level eventing and then onto the U.S. team

for the Pan Am Games that fall, held at the Fair Hill CCI*** (Md.). There, they earned team gold and claimed the individual bronze.

“Whitey basically got me going and made my career. I always wanted to represent our country, and I got to go to the Pan Ams with him, and that was huge and started it all,” Thompson said. “It’s funny that he would be the horse that would do it for me, since he would seem to be one of the most unlikely horses to do that. But he has the biggest heart in the world.”

With an unconventional jumping style and a cheeky personality, Whitey wouldn’t have been most people’s choice for their first international championships.

“He’s a little bit awkward to ride,” admitted Thompson. “He jumps like a giraffe. As you’re jumping the jump, his head and neck are coming back in midair. But when you ride him, he never makes you think that there’s anything he can’t do. If you get him in the general vicinity, he’s going to get it done. You might be sideways to the jump, but if you pull the rein, he’ll get over it. He doesn’t think that there’s anything he can’t do. That’s how he is about everything.”

Dutton might have been aware of Whitey’s limitations, but he had no qualms about recommending that they step up to the four-star level at Rolex. “It’s one of the parts of the sport that keeps us all going,” he said. “Whitey had complete trust in her, and he didn’t realize that he didn’t have quite as much potential as some of the other horses. He had complete faith in her, and Jan knew the horse inside and out, so it worked.”

After his Pan Am medals, Whitey returned to Rolex in 2004 and placed 15th. But later that year, he broke a splint bone and had to have it removed. This spring, one of Thompson’s students, Kathryn Shipley, bought Whitey, now 12, and has been earning ribbons at training level.

ADVERTISEMENT

Task Force Takes Her To A New Level
Whitey may have been the start of it all, but Thompson’s next two horses have taken her much farther on her path. Waterfront, a 10-year-old English Thorough-bred, is questionable to compete at Rolex because of some minor injuries this spring. But Thompson is on track with Task Force.

Task Force, a 14-year-old Australian Thoroughbred, might be more talented than Whitey ever was, but he’s proven to be a challenge all on his own.

“He’s obviously quite a talented horse, but he’s also one of the most difficult horses to ride at an event like Rolex,” said Dutton. “It’s a credit to Jan that she can get the good performances out of him. He’s a real big-time horse.”

“Phillip always tells me he’s crazy. I honestly get along with him very well,” Thompson said. “He’s been very good for me, because he teaches me a lot of patience. When I say he hears voices in his head, he honestly does. You can go out for a ride, and he’ll have multiple personalities. He goes from lazy pony to scooting across the field. He’s been very difficult just because he hasn’t been consistent mentally.”

This year will be Thompson and “Jedi’s” third Rolex together. After a sixth-placed finish at the 2004 Rolex, Thompson and “Jedi” were on the long list for the 2004 Athens Olympics and ended up as the third alternate for the team. Then, in 2005, they contested the FEI Eventing World Cup Final CIC***, at the Luhmuhlen CCI (Germany), and finished seventh.

“He’s gotten more mature every year. I keep thinking that maybe my riding will catch up to his maturing, but I still seem to go through the same things,” Thompson said.

“I was laughing at the beginning of this year, because he was going really well on the flat, and he was jumping well, and he looks better than he’s ever looked, which is fantastic. But I hurt my leg and had to take four weeks off in February. At the beginning of this season, I felt a little off kilter. He’s like ‘OK, I’m right ready to go. Mom, are you coming too?’ “

Thompson bought Jedi in the spring of 2001, and they quickly moved up to the three-star level by that fall, finishing at the Fair Hill CCI***. But in the fall of 2002, they had a fall at an advanced horse trials, and Jedi tore cartilage in his shoulder.

“They told me he’d never come back, and certainly never to the level that he’d been at. So, since that time, I think every event I’ve done on him has been a blessing,” Thompson said.

She carefully rehabilitated him, and they returned to the advanced level eight months later. They completed the Foxhall (Ga.) and Blenheim (England) three-stars in 2003.

But that September 2004, at the Burghley CCI**** (England), Jedi suffered another fall, at the next-to-last fence. He broke four ribs, punctured a lung, and fractured his hind pastern. But, amazingly, he bounced back yet again to repeat his sixth place at the 2005 Rolex.

“When he fell at Burghley, that actually took a lot out of me. I didn’t want to hurt him, and I was worried I would hurt him again. But once last year got started, and I got over my initial nerves, he never felt better. I think he’s a pretty tough horse,” Thompson said.

No More Sidelines
Thompson’s emergence at the top of the sport may seem somewhat meteoric on paper, but she’s been in it for a long time. She started riding in a Pony Club near Chicago, then became very active in Pony Club when her family moved to Englewood, Colo. When a friend of her parents traveled east to ride with Bruce Davidson and compete in 1983, Thompson tagged along to groom for her. She got to see the sport of eventing at its finest, and she was hooked.

“I absolutely loved it and knew it was what I wanted to do. So, I went and asked Bruce if I could be a working student,” said Jan, who was 15 at the time. “He told me I was too young! But after watching me help my friend out, he decided it was OK. I graduated from high school early, and two days later was in a truck and trailer on my way to Bruce’s. And not with my parents’ blessing at the time!”

ADVERTISEMENT

After three years as a working student with Davidson, where she moved up to the preliminary level and completed her first one- and two-stars, Thompson returned to the Midwest, and worked for a year for a hunter/jumper trainer. “I still had an event horse, who actually ran at Radnor but I really took the time to do that because I felt like I needed to understand the mechanics of the jumps a little better,” she said.

Then she spent a few years with Ralph Hill. “I learned a lot at Ralph’s. He had lots and lots of difficult horses, so you got used to getting on anything and everything,” she recalled.

But there was more that Thompson wanted to do. “I groomed a lot at that time, because I didn’t have a lot of money, and when I left there, I was very determined that I wanted to actually be able to be successful in a business myself, and also compete myself. I was getting a little bit tired of sitting on the sidelines,” she said. She moved to Middleburg, Va., in the mid-’90s to ride with David and Karen O’Connor.

But after a few years under their tutelage, she started riding with Dutton, where she remains. “Karen and David were very good about giving me more tools to make myself a better rider. They got me to the three-star level. But David wanted to concentrate on his riding more, not teaching, so I started riding with Phillip. When I went to Phillip, I said, ‘I want to be more competitive. I want to be in the game.’ He looked at my three nice horses and asked me why I wasn’t winning with them,” Thompson said.

Dutton’s guidance has helped Thompson put the finishing touches on her performances and advance to the level of being competitive at the top. “She’s really dedicated and a real competitor. She’s committed to doing whatever it takes to improve her riding and her horses’ performances,” Dutton said.

Thompson hopes that her new edge will pay off at Rolex. “Kentucky is such a fantastic place to compete, even with the nerves about it being such a big competition. The public is great to you. I’ll never forget, with Whitey, my first year there, little kids coming up and asking for my autograph. I was like, ‘No, you mean somebody else,’ but they said, ‘No! Yours!’ It’s an honor to be able to compete there,” she said.

Making A Living
Thompson has also developed a reputation as a source for quality event prospects. While she’d always bought and sold horses, she began importing horses from England consistently in 1997. Among the list of horses she’s sold are three-time Rolex winner Winsome Adante and John Williams’ Sloopy.

“I really believe that every horse has a home and a niche, and I love picking them out and finding that for them. It’s fun to pick out a type that can be successful for someone,” she said. And while many may question why she sells top prospects rather than keeping them to further her own career, Thompson knows the reality of the situation.

“You have to be excited about the prospect of someone else riding them and being successful. And the bottom line is that it is about the money. You have to support yourself, and if somebody’s going to give you money for a horse, you have to sell it,” she said. “The horses that I have kept to compete have literally just been circumstance. My horses maybe aren’t the most talented, but they’re good for me. People think I keep all the good ones, but I sell a lot of good ones because I have to!”

In the last five years, Thompson has developed a solid base of business in buying and selling, and teaching and training out of her Surefire Farm in Purcellville, Va. And at the end of last year, Thompson added a new owner, Chips Chester, to her roster.

The avid foxhunter has purchased Task Force for her to ride, enabling Thompson to continue to concentrate on making him even better.

“I think that’s what my career lacks more than anything, is a support system of good owners. It’s hard, unless you’ve had a lot of success,” she said.

But Thompson has a lot of great behind-the-scenes help. “I have a great support staff. Pippa Moon basically manages the barn at home and has a horse at the intermediate level. Natalie Varcoe-Cocks pretty much is my right hand and left hand. She goes on the road with me; she’s traveled to every competition with my horses. My staff is fun, because I try to give them perks of the job that make it worthwhile. Helen Murray and Kristin Rozycki do a bunch of riding and work at home. Everyone gets along really well, and no one’s afraid to do any job,” she said.

That willingness to pitch in comes in very handy in the summer, when Thompson will help run the third year of the Surefire Horse Trials, a USEA-recognized event that offers beginner novice through intermediate levels. The event started in 2004 and grew in popularity, and it will run on July 1-2 this year.

“It’s really fun to give back to your sport and to see a lot of people who you know from events at your farm,” said Thompson.

Categories:

ADVERTISEMENT

EXPLORE MORE

Follow us on

Sections

Copyright © 2025 The Chronicle of the Horse