By Lila Gendal
Portraits and Styling by Shawna Whitty
What happens when a tearful and fearful 4-year-old girl’s first pony is also 4 years old and so naughty she’s nicknamed Satan? A recipe for disaster would be a solid prediction, though in Caitlyn Connors’ case, the answer is that a brave, capable athlete was created—eventually. “I was not a brave rider as a child—I cried a lot and would get so nervous I threw up on the way to horse shows,” Caitlyn admitted.
Unbeknownst to her, Caitlyn’s formula for success started brewing every time she faced her fears and threw a leg over a bucking, leaping, bolting, rearing or stopping horse. What started off as some quality time faceplanting in dirt as a child has morphed into a thriving equestrian business in Wellington, Florida, and she credits most of her success to her diverse background with horses.
Growing up in Glen Mills, Pennsylvania, within close proximity to the Devon Horse Show, Caitlyn found the equestrian life not only irresistible, but inevitable. “My mom rode, so she’s the one who got me into horses initially,” Caitlyn said. “My first pony was the worst thing to ride, and I would fall off of her three times a day, which honestly developed me into being able to ride anything because I had to suck it up, get over it and learn how to ride her.”
After graduating from the stubborn pony, Caitlyn began helping with the riding and selling of hunters, jumpers and equitation horses. “I started helping my trainer at the time sell horses. I was only 8 years old, and people started to inquire who this small child was riding around on Junior hunters,” she said. “I was riding a hundred different types of horses, ones that refused, reared, etc., and then I started breaking racehorses for a summer job.”
Favorite Horses
Many riders and trainers seek out certain horses to buy, but for Caitlyn, most of the horses that she’s crossed paths with have found her. “The majority of my horses have come into my life coincidentally, except Bink, whom we found in 2012,” Caitlyn said. “My mom rides him now, as he’s retired in Pennsylvania, but he was the first horse I ever tried and then ended up buying. At the time, he was a 6-year-old and I was 12 and we jumped crossrails up through the FEI four-star level.
“Another horse that’s important to me is Express Blue; he came into my life when he was the only option I was given in a trade deal. When I was told this option was 5 years old and only jumping 0.70m, I had no choice but to accept the offer because the horse I had had a stopping problem—jumping anything was better than not jumping at all! Express Blue turned out to be partially blind in both eyes, had a heart murmur and acted like a stallion, but I absolutely adored him. He’s one of my favorite horses. We have jumped everything from the .65m all the way to the five-star classes.
Caitlyn balances her time riding, competing and running a successful training and sales farm in Wellington. “I attended the University of Miami and graduated in May,” she said. “I’m guessing horses will turn into a full-time business for me, though I do have a passion for fashion, which I might explore at some point in time. I really love my horses and I’m so grateful to be able to balance riding and pursuing a career. I also enjoy working with the younger horses and bringing them along.”
In order for Caitlyn to maintain her riding at a high level, especially while remaining open to the career possibilities of the future, takes an equally high level of support—Olympic level, in fact. “I train with Roberto Teran and he’s been amazing to work with, giving me lots of opportunities, and we mesh well,” she said, adding that Roberto, who competed in the 2020 Tokyo Olympic Games, has been a huge part of her equestrian career. “I’m blessed to be able to train with him and I think he gets the best out of me and my horses. We’ve been working together for 6 years now.”
“Caitlyn is a naturally talented rider, very competitive and rides incredibly well under pressure,” Roberto said. “She’s very organized, determined and she has huge dreams. She has all the qualities and attributes needed to make a top rider and competitor.”
Caitlyn has overcome huge obstacles from a young age and continues to shine both in and out of the ring, though she admitted to a couple of challenges she has faced as a rider. “While I’m very fortunate to have supportive parents and they’ve helped me immensely, we’re not in a position to buy multiple top show jumpers,” Caitlyn said. “That being said, I’m grateful to have some amazing horses in my string and to be able to ride and compete full time right now.”
Mental Challenges
Mentally preparing to jump massive obstacles in front of huge crowds alongside Olympic athletes cannot be easy, no matter who you are. Caitlyn said her routine for a night class is to take a nap, refresh herself, listen to music and get into the zone. “I actually have horrible anxiety, which I am very open about,” she said. “It’s important for me to not overthink the big classes. I go in the arena and I walk everything, and once I have my plan, I leave. If I stay in the ring, I’ll start questioning myself and my plan. I’ll watch a few horses, but if I watch too many, then I start second-guessing myself. I always have to find that balance.
On the flip side, Caitlyn said her biggest strengths are her dedication and drive. “I will dig in deep and make it happen because I basically grew up as a cowgirl riding wild horses,” she said. “I learned the hard way to be prepared for anything that could happen, whether a horse stops, or bucks, or any type of challenge that came along. I also learned to ride a wide range of horses, which has turned into a great strength.”
This year, Caitlyn participated in the Under 25 (U25) division at WEF, a fantastic opportunity to show in big divisions without having the added pressure of competing against Olympic athletes. “I love being a part of the U25 series, and I’m grateful to Hermés, the sponsor, giving us this amazing opportunity,” Caitlyn said. “I highly recommend this division to any up-and-coming riders looking for a great experience. I am 22, so I have a few more years to be a part of the U25 series.”
Caitlyn is excited about her talented string of horses. “I have three horses right now. Express Blue is taking a break after a busy fall and winter season,” she said. “He’s been doing so much for me since he was 6 years old. Sometimes I just like to give him a break and let him have his time because he loves being in his field.
“Scott Keach and Ana Christiana Gansauer gave me Falcon in 2022 to do the U25 series with and I’m so grateful he’s in my life, he’s an extraordinary horse. Falcon is so sweet and tries so hard every time I go in the ring—even if I’m jumping cavaletti at home, he gives 100%.
“Lastly, I’m riding a sale horse named Pira, an 8-year-old chestnut mare and I’m very excited about her. She’s owned by Roberto and I’m so grateful he gave me the opportunity to work with her. She is super special, and I cannot wait to see what her future has in store.”
Family and Her Future
Caitlyn graciously offered some sage advice to any up-and-coming riders looking to get their foot into this industry: “Ride anything you can get your hands on, because every single horse will teach you something. Reach out to other professionals in the industry. You never know what opportunities are available, and take the time to watch good riders in the ring as well as the warm-up.”
When Caitlyn isn’t riding or advancing her career, she can be found hanging out with her family. “I am very family oriented,” she said. “My little brother is an avid hockey player, so I grew up watching a lot of hockey with my family. If there’s ever a free weekend and he has a game, I love to go and watch him, and see my parents.”
Being family oriented extends to Caitlyn’s horses as well. “My horses are my pets and I’m obsessed with each and every one of them,” she said. “My horses are loved, spoiled and well cared for.”
For more information, visit caitlynconnorsllc.com and on Instagram @caitlynconnors
Photos by Shawna Whitty/SAS Equestrian, www.sasequestrian.com and on Instagram @sasequestrian