Jenny Spain admits she’s always been one to look toward the future, and she has trouble living in the present moment. But last autumn, the amateur dressage rider allowed herself to celebrate a huge accomplishment when she earned her U.S. Dressage Federation gold medal on her self-made off-the-track Thoroughbred Some Caan Job.

Spain, Catlett, Virginia, had trained her now-retired OTTB Turnaround Tony to Grand Prix in 2017, but she had yet to earn her gold medal. She and Some Caan Job, or “Annie,” made their Grand Prix debut in 2024, and after a few starts where they earned just below 60%, they earned the final score needed for gold with a 64.10% at the PVDA Fall show (Maryland) in November.

“I kind of jumped up and down and screamed in the office for a moment,” she said with a laugh. Then she went to the USDF Awards Banquet in Houston, Texas, in December to receive her medal.

“It’s unusual for me to do that kind of thing—spend the money to get those kinds of awards and take that kind of time,” she said. “I just thought it was important to do that, to allow myself that recognition and to just to realize that that was a big accomplishment, and it’s OK to be excited and to live in that moment for a little bit. I tend to always just kind of look to the future so much that sometimes I don’t allow myself the good feeling that the present can give you.”

Spain, 46, is the co-founder and program director at Simple Changes, a therapeutic riding center in Northern Virginia. She got into dressage through her now-wife Melinda Freckleton, DVM, after working and riding in the hunter/jumper industry.

She rode her first Grand Prix test with Turnaround Tony (Belong To Me—Glamour Girl, Black Tie Affair) in 2017, a year after she’d found Annie as a 3-year-old.

The Retired Racehorse Project Thoroughbred Makeover had started a few years earlier, and Spain thought it would be fun to take a horse there, so she aimed Annie at the annual competition held in Lexington, Kentucky.

RRP Success

Annie (Square Eddie—Caan, Crowning Storm) had 15 starts on the track in California but was in Pennsylvania when Spain found her. She liked her movement and the kind look in her eye.

Spain spent the first two months working with Annie on groundwork and long lining through the winter and got on her in January.

“I’m really a fan of teaching them to long line before I get on because then the steering and the two-rein contact, and the concept of what that means outside of the racing world to the horse, has been taught,” she said. “She was quite good at all that. By the time I got on her, she was just easy walk, trot and canter and get her leads each way.”

The pair headed to Kentucky in the fall of 2017 and were first out of 80 riders on the initial day of the dressage competition. “By that next day [for the final], she was getting a little fried,” she said. “It was in the coliseum with the Jumbotron, and she really was not sure about that, so, she was really tense in the finals.”

They ultimately finished fourth, with Spain the highest-placed amateur rider, and she was proud of her young horse.

Annie needed some time to decompress from RRP over the winter, and by the spring, she was back to work and moving up the levels with Spain and help from her trainer Patrick Tigchelaar.

Medical Setbacks

While Annie was working at Prix St. Georges in 2021, a routine preventative gastric ulcer scope revealed she had an entrapped epiglottis. She’d never had breathing issues prior, but Spain was advised to have a surgery done to cut the epiglottis free so it wouldn’t cause trouble down the road. She took the mare to Marion duPont Scott Equine Medical Center in Leesburg, Virginia, for the surgery. 

When vets took Annie in for surgery for the simple procedure, they realized it wasn’t a typical case because the epiglottis had been trapped for so long that it had developed fibrous tissue around it. Annie had to go back for surgical revisions four more times over three months because the area would form adhesions, then re-entrap and need to be cut free. 

Annie later started to make noise while under saddle, and Spain began feeling issues in her rein contact, so she took the mare to New Bolton Center (Pennsylvania) about eight months after her surgeries in Virginia. Vets discovered the epiglottis had become misshapen and wasn’t functioning correctly, so they performed a tie-forward procedure and gave Annie a 50/50 shot at returning to upper-level work.

“She mostly does fine” now, Spain said. “There are times that I could tell it does displace some, and she can make a little bit of noise, and I could tell again that she feels a little bit different into contact, but she doesn’t do it often, and we figured out what she tends to need, and it’s just trying to keep her in that right place so that everything stays in the position that it should be.”

The pair were back in the ring briefly in 2022, then Spain dislocated her kneecap in an accident with another horse and was laid up for most of 2023. Finally, in 2024, they made their Grand Prix debut.

A Unique Challenge

Spain says that riding a Thoroughbred at the upper levels of dressage is a unique challenge, but one she’s happy to take on. 

“I think the biggest thing is just that a very good-moving Thoroughbred is generally not as good a mover as the warmbloods,” she said. “So that does mean you have to be that much better in the movements and in your accuracy.”

It’s frustrating to see a bigger, fancier mover score better when Spain feels she and Annie rode a cleaner test, she acknowledged, but said that comes with the territory. 

“People may argue that, but I think most people who do this recognize that that is the reality,” she said. “You have to be accurate; you have to hold yourself accountable, and you have to keep working to make your horse be the best mover it can be.

“I don’t really honestly care if we win a class or don’t win a class, because I always go back to the idea of, like, I paid $2,500 for my horse,” she continued. “At the end of the day, if I don’t win by a point or two or whatever, that’s all right, because I’m there, and I’m doing it, and I think I’m doing it pretty well. I don’t have that kind of money to spend. Most of the horses I’m competing against are six figures more than what Annie was, which is fine, but it’s just reality.” 

Spain noted that while many people question whether a Thoroughbred can do the upper levels of the sport, she thinks the bigger question is whether the rider can do it.

“I push myself all the time, and I have a very good trainer, and that’s a big part of it,” she said. “I may not have spent much on the horse, but I certainly spend my money with having a very good trainer. I do this on a shoestring budget, but I’m out there riding my horse, even when sometimes I don’t want to be or I’m busy, or I’m tired. I try to hold myself accountable to it. I had luck, because anything could have gone wrong, and any of this could have not worked out. So, I’m lucky too for this moment, but I also know that luck can change, and I have to be OK with that and come up with whatever plan will be next and see where that goes.”

Besides the affordability of a Thoroughbred, Spain also says she likes to be a bit of an underdog because it keeps things interesting.

“I don’t even know what I would be like if I got to sit on a horse [bred for dressage.] I know it’d be such a different mindset,” she said. “I’d love to try it one day, to sit on a really nice horse and be like, ‘Don’t screw this up.’ Because, if you don’t get in their way, they can do it. Whereas with what I do [with a Thoroughbred] is like, OK, I have to create this. I still have to ride really well.”

One advantage of riding a Thoroughbred, she said, is their can-do attitude and heart—upper-level dressage might not be as easy for them as for a warmblood, but “they’re the ones who are just going to really try to figure it out.”

Spain’s goal for 2025 is to create a freestyle and improve their scores at Grand Prix to the mid-60s and qualify for the GAIG/USDF Region 1 Championships.