At just 24 years old, Lillie Keenan is one of the most talented show jumpers in the United States. With a maturity beyond her years that has been evident since she started riding horses, Keenan used education, both in and out of the competition ring, to advance her career. Having recently made Wellington her full-time home, the New York City-born equestrian is reaching for new heights and learning along the way.
Keenan first came to Wellington at the age of seven, when she convinced her parents to forgo a skiing trip on their winter break from school and instead travel to South Florida for her to compete on her pony Aspen Spring. They have since spent every winter traveling to the warmer climate. “That is why I still don’t know how to ski!” she noted.
The talented young rider has made a habit of convincing her parents and others of what she already knew: her passion for horses, riding and competing would always be foremost in her life. While horses take center stage, Keenan has also valued the importance of education and all of the relevant skills that come with learning.
Keenan said that her parents, Pam and Howard, were “used to sacrificing for their kids’ passion,” with her older brother being a professional hockey player and her sister a professional ballerina with the New York City Ballet. For Keenan, it meant her mother, who was a successful junior rider herself, ferrying her to ride with Andre Dignelli and Patricia Griffith at Heritage Farm and traveling to horse shows throughout the year, including to Wellington every winter. “They were incredibly supportive,” she said.
As a student at the Spence School in Manhattan, Keenan commuted every winter from ages eight to 17, her junior year at Spence. “JetBlue was like a second home to me,” she laughed. “I was in a position that my family could make that possible, so I was very lucky. I kept my grades up and was allowed to do it. [Spence] set me up for success with academics and with sport. They made it possible, but taught me discipline, and I could manage to do well in school while also jumping five star [Grand Prix classes] while still in high school.”
This sometimes required taking matters into her own hands. “When I was in eighth grade, I spoke to my head of school about missing every Friday for three months,” Keenan recalled. “She explained that anything is possible as long as I’m the one who makes it happen. I had to talk to the head of school and my teachers myself, rather than my parents. I had to be responsible for my own work and time management. If I missed anything, I had to make a plan and communicate. I was comfortable with it.”
While Keenan visited six schools for higher education, Harvard University was her first choice. “It was the one place that I had a feeling that I could be myself there,” she said. “What made Harvard different was that every person that I met there, they didn’t have to understand show jumping and horses, but they had something in their life they were passionate about, too. They were driven by something; it connected all of us.”
Keenan continued her equestrian passion through her college years.
“I don’t remember feeling like I wished I wasn’t doing both,” she explained. “I didn’t want to miss out on a once-in-a-lifetime opportunity of the experience of moving away from home and being a college kid. I liked it, but I realized there was never a moment at a party or something that I wasn’t missing horses and the sport. Once I realized horses is what I wanted to do, I was able to commit myself better to studies and sport. At school, I was at school. When I wasn’t, I sat down and got work done.”
In a remarkable junior career that included wins in the USEF Pony Finals, the ASPCA Maclay Finals, the USEF Medal Finals, the Washington International Horse Show Equitation Finals, double gold at the North American Young Rider Championships and winning the USHJA International Hunter Derby Finals against a full slate of professionals, Keenan kept her laser focus on her goals.
She jumped in her first Nations Cup at the age of 17 in Bratislava, Slovakia, and turned professional in 2015 during her freshman year at Harvard. In 2017, she was a part of the first all-female team to win the Aga Khan Trophy in the Nations Cup at the Dublin Horse Show. She has remained not only one of the best Under 25 riders in the world but is also consistently one of the top 10 riders in the country.
Keenan has fond memories of growing up wintering in Wellington at the Winter Equestrian Festival, watching the Grand Prix classes under the lights at 10 years old and feeling that she would never jump that high, and then four years later being anxious to try. She rode in her first Saturday Night Lights with Pumped Up Kicks at 17 years old.
“The crowd there is a different experience than a lot of shows,” Keenan said. “The atmosphere is electric. The crowd definitely raises you up.”
After graduating from Harvard, Keenan turned her commitment full-time to horses and show jumping. “After 15 years or so, my focus was on one thing,” she explained. “I really looked forward to it; I never had that other than in the summers.”
Keenan has now made Wellington her permanent residence with Chansonette Farm, and a bonus of being in one place so much is the chance to go to the local Pilates Rocks every day.
“It has really become home,” she said. “It’s the only time in my life where I have lived where my horses are and had that constant every day, where I can wake up and go and ride. I love having other [equestrian] disciplines at such a high level so close to home. I enjoy watching dressage and learning from seeing that. I think it’s a very unique community that you don’t find anywhere else in the world.”
Keenan’s current string includes top horses Fasther, Skyhorse and Agana van het Gerendal Z, along with promising nine-year-olds El Balou OLD and Cazaan, as well as Ann Thompson’s eight-year-old Delta de la Rasse. It’s a family affair, as her mother Pam helps pick out young horses and develop them for the future.
“From the very beginning, one thing my mom never pushed to try was riding,” Keenan said. “When she stopped riding, it was hard to give up; it was her entire life. This sport is so up and down, and you lose a lot more than you win. You need support and people around you to understand how much commitment it takes. Horses are always going to be the priority. I’m very lucky that I get to share that with my mom.”
While it has been two years since she graduated, Keenan’s love of learning continues. Six months after she left school, she was tutoring high school students. “I love learning, and there are parts of school that I really enjoyed. I think that will be true for life,” Keenan said. “That’s why I started my own business with designing show jackets, and I push myself in new ways, in more than just sport. It makes me a better rider and a better person.”