By Laura Scaletti
Portraits by Melissa Fuller
Chapin Cheska may not have been born in a barn, but it didn’t take her long to make her first visit. The daughter of Donald and Cara Cheska, Chapin went straight to the barn on the way home from the hospital.
“The first person to hold me outside of the hospital was ‘Mr. Clean,’ Miguel Murillo, who still works for my family today,” Chapin said. “We are a big barn family. I grew up in a really special environment, and to always have been around horses is something I wouldn’t trade for the world.”
Before Chapin was 2 years old, she got her first pony, Pinky, thanks to her Uncle Robert. “Pinky taught me how to walk, trot, canter and jump. She pulls a cart, does Western, plays polo, is potty trained and goes into the house,” Chapin said. “She was basically my babysitter growing up and taught me so much. She’s still with us today and goes everywhere with us. We joke that she’s the favorite daughter, because of how much my parents love her.”
Pinky isn’t the only daughter to travel with Cheska, Inc. as they go from horse show to horse show. Chapin joined Cheska, Inc. in a professional capacity in October 2025 as soon as she turned Pro. “After I aged out, my parents really encouraged me to take some time to explore experiences outside the ring and make sure this was truly what I wanted to do. For two years, I still rode, showed and was in the barn almost every day, but I also spent a lot of time working in other areas, mainly product development. I’m grateful for that period, and even more grateful that I still get to pursue that passion alongside riding—but I can’t see myself doing anything other than riding,” Chapin said.
Backyardigan
As Chapin grew up, Donald and Cara instilled the importance of treating each horse as an individual and doing things properly with each horse she handled, rode and competed. “I learned that you can’t really compare horses, because no two horses are alike. You have to get on each horse with a clear mindset and not allow yourself to carry anything from your previous ride or day when it’s your time to work with that horse,” Chapin said.
Chapin believes it’s also important to look at the bigger picture and realize that not everything is going to go according to plan. “Sometimes you have to regroup and just take it day by day,” she said.
Part of what helped Chapin learn these lessons early on was that her parents raised her in an environment where she had a proper equestrian education that was balanced with letting her be a pony kid. “They let me be a bit of a backyardigan with my horses and ponies, which I think was important. That helped me develop strong relationships with our animals from an early age and I’ve always considered them to be part of our family,” Chapin said. “To this day I still like to just play with our horses and will jump on them, including our stallion Kentucky Van’t Ruytershof, bareback and with a neck rope.”
While Chapin had success in the show ring growing up, some of her favorite moments at horse shows as a child happened outside of the ring as she hung out with other children of professionals during the long horse show days. “We’d show in the morning, ride our ponies back to the barn, change into shorts, put our backpacks on and head out on our ponies for the rest of the day. We’d go to the food stand, make a picnic to have with the ponies and ride out to the middle of the cross-country field at the Kentucky Horse Park to enjoy it,” she said. “I was also known to take a fishing rod and fish off the back of my pony.”
Today Chapin laughs when she shares those stories with her students. “I tell them you can’t really take advice from me because we had special ponies. Most ponies wouldn’t tolerate the stuff we did back in the day, but I was so lucky to have a great mix of doing it the proper way while also being allowed to be a kid and truly enjoy my pony,” Chapin said.
While her parents have been there for Chapin from the start, both in and out of the saddle, they made it a priority to bring in other trainers to help Chapin become an educated horsewoman. “It’s a good balance to hear voices other than your parents’, and I think that helps keep the family dynamics happy. When I was 10 years old, Hayley Barnhill began working for Cheska, Inc. and started helping me,” Chapin said.
Working with Hayley, Chapin competed in her first 1.0m classes all the way up to Young Riders and High Juniors. “At the beginning I was quite starstruck, as I idolized her. We laugh now because she’s one of my closest friends and has become part of the family,” Chapin said. “I’m so lucky that I still get to watch and learn from her each day.”
Horses of a Lifetime
In 2019, Chapin was lucky to purchase Hello Gov’nor, or Guv. With Scott Brash in the irons in 2017, Guv went double clear in the prestigious Nations Cup in Aachen. After being sold to another young rider in America, Chapin got the opportunity to make Guv her own.
A quirky, speedy horse who wasn’t the easiest, Guv proved to be an incredible gift for Chapin’s riding. Donald was the one who made this dream partnership a reality. “My dad bought him no trial, no vetting, he just knew the horse. It was a bit of a gamble because he wasn’t the most rideable horse, but it paid off,” she said.
Although Donald and Chapin were thrilled about owning Guv, they kept the news under wraps from Cara. “We didn’t tell her for like three days until she walked into the barn and asked why both of us were smiling like we were. So, we fessed up,” Chapin chuckled.
At first, having a horse of that caliber underneath Chapin was a bit overwhelming. “All eyes were on us so that was a bit nerve wracking. However, one day it just clicked and we formed a true partnership. To have a horse like that so early in my career was incredible,” she said.
After showing him for two years, the Cheskas decided to retire Guv while he was still healthy and sound. “We gave him the retirement a champion like him deserved until he sadly passed away in 2024,” Chapin said. “After he was retired from showing, he still taught me so much. He was the best horse to take on a trail ride, ride bareback—he was always up for anything. I even attempted to teach him how to play polo!”
In 2021, while on a horse shopping trip in Europe, Chapin visited Axel Verlooy at Euro Horse. It was there that she walked into the barn and saw the most beautiful animal she’d ever seen: Kentucky Van’t Ruytershof.
“My mom had given us one rule for that trip, and it was to bring back a maximum of two, maybe three, geldings. We ended up bringing home a mare, three geldings and Kentucky was a stallion. We assured her that Kentucky would be gelded before he came to the States; however, she learned that wasn’t the truth when we got a call from quarantine and she heard on speakerphone, in the car, that our stallion had arrived and he was beautiful and well mannered. She was not pleased with us at that moment,” Chapin laughed. “When she met him in quarantine, she said, ‘He’s pretty, but he’d be a lot prettier as a gelding.’”
A 1.55m jumper previously ridden by Jos Verlooy, Harrie Smolders and Denis Lynch, Kentucky is known for his outstanding quality, scope, conformation, intelligence and amazing bloodlines (his sire is For Pleasure, his dam sire is Diamant de Semilly and his dam is a full sister to Emerald). Initially bought to be a hunter stallion, Hayley showed him for the first time in America in a hunter derby. However, his hunter career plans changed after Chapin’s horses were all a bit older and about to retire.
“It was a joke as I walked down the barn aisle looking for a horse I could show. I would say, ‘What about Kentucky?’ The last thing I needed at 16 years old was a big, beautiful stallion, but I was obsessed with him, so that was secretly my plan to make him mine,” Chapin said. “All of a sudden my plan came to fruition; I began showing him and he went from being a sales horse to my horse.”
Chapin is hoping to move up to the U25 classes with Kentucky soon. “Every class I have with him is something I’m grateful for; I can’t wait for what’s ahead. I’ve learned so much from him already, and I know there’s still so much more he has to teach me. To have my name added to the list of incredible riders he’s had throughout his career is really special. I’m so grateful he chose me as his person,” she said.
Stallion Manager
Chapin stumbled into being a stallion manager at age 16. “We had a mare, Beezie, that we sold and as part of the deal they asked if we could breed her to Kentucky. I showed up with Kentucky to get him collected and normally they have a stallion handler, but apparently that person wasn’t working that day,” she said. “So, there I was holding him, and they told me, ‘Alright, lead him up.’ From that point on, I’ve handled all his collections.”
As Chapin’s “chillest horse,” Kentucky can go from bareback trail rides to competing to his breeding duties without a change in temperament. “He’s never studdish and only acts like a stallion when we put on his special boots and equipment he wears for breeding,” Chapin said.
Managing Kentucky’s breeding has been a full-circle moment for Chapin. “We’ve always had some sort of a breeding operation, so I’ve always been around stallions, fell in love with them and have a false sense of reality they are all easy to be around. Since I was 6 years old, I could watch any Grand Prix and tell you who the horse was by and how it was somehow related to one of the horses in our barn,” she said. “So, it’s been really fun to now coordinate Kentucky’s breeding.”
Chapin is excited about producing quality offspring in America. “Europe has such a strong breeding program, with so many stallions standing over there, so I think it’s really important to try to keep the breeding program in America alive. I hope I can play a small part in breeding and developing young horses in America,” she said.
Kentucky stood in Belgium and Sweden prior to arriving at Cheska, Inc. “I try to follow all of his babies and see what they’re doing. One of his horses was just champion of his SBS approval in America. It’s really special to watch his offspring as they’re getting older and starting to jump Grand Prix and international classes,” Chapin said. “It’s cool to see what he’s doing for the future of the sport. I’m especially excited about our 6-year-old by him, Topaze Van Het Reigershof, whom I got for my 19th birthday. She shares so many characteristics with Kentucky, both in how she goes and how she feels to ride.”
As Kentucky’s manager, Chapin wears many different hats. Not only does she compete him, she manages his collections, evaluates mares to see if they are good breeding candidates for Kentucky, built his stallion website and learned how to create breeding contracts.
“At the end of the day, I don’t stand him for the money. It’s more of a passion project for the future of the sport. With that in mind, I’ve created different feeds and discounts to make breeding to him more accessible. It’s definitely not cheap to produce young horses in America, so I try to help out where I can,” she said.
All Around Equestrian
In addition to competing Kentucky, Chapin has recently discovered a passion for developing young horses. “It’s so rewarding to work with them because it’s never a linear process. There are ups and downs, but when everything comes together you can really see your hard work come to fruition,” Chapin said.
Throughout her career, Chapin was fortunate to ride older horses who were stepping down and taught her the ropes. Now that the roles are reversed, Chapin’s learned to look at the sport a bit differently. “I’m a bit of a perfectionist when it comes to my riding, so working with the young horses has been great for my riding. There’s almost no pressure because the goal is to give the horse a good experience each time. Even if the rounds aren’t perfect, there’s probably something they learned in that course,” she said. “You might be a little deep, a little long, they wiggle, but when something clicks it’s one of the best feelings in the world.”
A Jill of all trades, in her free time, Chapin works as an independent contractor for several equestrian companies. “Companies will come to me with a need for a product or a problem for me to solve. I come up with a prototype and test it. Most of the time, Kentucky is somehow involved in my testing as I use him as the model for my prototypes,” Chapin said. “Every product I create is designed with the horses’ well-being at the forefront. If something I make can genuinely improve even one horse’s day-to-day life, then I feel like I’m doing something that truly matters.”
She’s also a self-taught leather worker. “I was sitting on the couch one day, three years ago, and had an idea for a hackamore that had no leverage, basically like riding in a halter. Kentucky is very light in the bridle, so I thought, I bet I can make that, and ordered a $20 kit off of Amazon. The first one I made was quite bad, but then it started clicking and I’ve begun selling my hackamores to a lot of professionals,” she said.
Bertram Allen uses one of Chapin’s hackamores on his five-star show jumping horse. Once other riders saw him using it, Chapin’s creations took off. “It’s been really cool to turn on ClipMyHorse and watch a Grand Prix and notice that horses are wearing my products. I don’t promote my products and it’s all through word of mouth,” she said. “It’s another one of my passion projects. I think it’s really good to come home and do something creative at the end of the day and have a clear headspace.”
As Chapin looks forward to her professional career, she’s excited to carry on her family’s legacy at Cheska, Inc. “If I’m able to achieve even a fraction of the careers they’ve had, I would be more than happy,” she said. “It will take a long time to even make a dent in that, but I truly enjoy the process and everything I’m learning along the way.”
Follow Chapin on Instagram @chapincheska, @cheskainc and @kentuckyvantruytershofstallion
Photos by Melissa Fuller, melissafullerphotography33.mypixieset.com
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