Jan Benjamin still remembers her daughter’s first hunt trail ride. Makayla was about 4 years old, she recalls, perched proudly on top of her pony, Marshmallow. “How was it, Makayla?” the field master asked her. Makayla sighed. “A little bit slow,” she replied.
Seventeen years later, Makayla Benjamin ’18 would be the first in her family — and the first Sweet Briar student — to win the coveted Cacchione Cup, the nation’s highest honor for a collegiate rider. It was the first time she’d even qualified, during her senior year at Sweet Briar.
But her historic victory had been long in the making.
“Makayla started riding when she was a baby,” Jan says. “I would put her in front of me on a horse, between my arms.” It’s no surprise the two have been best friends ever since, bonding over their shared passion. Jan herself had owned horses since she was a child, so they’d been a staple of the Benjamin family and their home in Lucketts, Va., from the start.
There might not have been a Benjamin family without horses — after all, it’s how Jan met her husband, Andrew: The two competed together on Purdue University’s Intercollegiate Horse Shows Association team when Jan was a freshman. Andrew graduated the next year, but as soon as Jan finished college, they got married. Seeing their former Purdue coach again at this year’s IHSA nationals — and grabbing him for a group photo with Makayla — was “really neat,” Jan says.
Did she expect Makayla to win the Cacchione Cup? Nope. “I mean, it’s the top riders in the country,” Jan says. “I was hoping for her to be in the top 10, you know. When we were there watching it, and once they announced the fourth-place rider, I turned to my friend and said, ‘She won it.’ I knew the other two riders, and I had taken notes through all of the classes. I was like: ‘She won it. They can’t beat her.’”
“We were all shocked and crying for joy,” Andrew Benjamin says. “All I could think of was, ‘What a year, and this is the best possible way to cap her college career!’”
Makayla was 5 when she entered her first horse show. Jan didn’t want her to show until she asked to do it. “It was more important for her to learn how to ride, and how to take care of horses first,” Jan explains.
And Makayla did.
“I think I was so involved with horses from the get-go that each moment just reassured my interest in horses and the sport,” she says. “I liked to be able to see my own progress with a horse. It was always challenging and frustrating, but so rewarding at the same time. I think being able to work with horses my entire life gave me such an appreciation for being patient and humble. And I loved that about them, so I think just being able to learn so much about them developed my deep interest in them.”
Makayla showed ponies for several years and competed in the Pony Finals when she was 11 and again when she was 14.
Soon after, she moved on to horses and throughout high school, learned the ropes of equine care as a working student at Gavin Moylan Stables. At 16, Moylan put her in charge of all the horses he left at home while going to Florida for the winter. “He had a horse that was pretty much broken mentally, that no longer would jump,” Jan remembers. “That was her project over the winter — to work with him and get him going again.” By the time Moylan returned, his horse was jumping just fine. Makayla kept the horse from December until August and, in partnership with Moylan, made enough money selling it to import a new horse from Germany.
In order to work with her new horse, Makayla completed her high school credits early and spent her final semester in Florida. Then the Benjamins sold the horse and she was off to Sweet Briar — a place she had fallen in love with as a flower girl when she was 6 years old. A few campus visits confirmed it was still as magical as her memory. And that magic continued.
“My experience at Sweet Briar was phenomenal,” Makayla says. “I will forever cherish the friendships I made there, and the relationships I had with my professors, who were always so supportive. The entire environment truly made it seem like you could accomplish anything you dedicated yourself to. Sweet Briar taught me how to fight for something I love and believe in, how to be a good leader, how to face challenges and overcome them, how to be involved, and how to manage it all.”
Her first semester was a blur of equitation finals, with little time for academics. She was planning to catch up over the summer, her mother remembers, to make sure she’d be in good shape to major in engineering. And then March 3, 2015, happened: Halfway into her second semester, Makayla — and everyone else in the Class of 2018 — found out the College was closing. Or was it? Makayla took action. On April 20, she and one other student filed a lawsuit against Sweet Briar’s previous board.
Her father, now vice chair of the current board of directors, remembers it well. “When she testified in court and was asked to explain her thoughts about the closure, the first thing she said was, ‘I have lost my home.’ To me that made it worth fighting for in earnest,” he says.
While painful, the near-closure and subsequent saving of the College played a huge role in Makayla’s personal development. “I did not know that I was going to have to take the stand, but I am so thankful that I did because it helped me to believe that I could fight for something, and I would be heard,” she says.
The summer’s uncertainty put her behind academically, so Makayla had to change course: She dropped her engineering major to a minor and went for a mathematical economics major instead, with another minor in business. But she’s glad she was able to stay at Sweet Briar. So is Jan.
“We looked at other colleges, and all it confirmed for us was that [with] Sweet Briar, we made the right choice the first time.”
And 2015 wasn’t over yet for Makayla. That winter, she qualified for the AIEC-SRNC World Finals in Marburg, Germany — as one of three riders on Team USA. And she ended up winning the show jumping competition. Back home, then-President Phil Stone organized a special awards ceremony to greet the champion. “President Stone was amazingly supportive,” Makayla remembers. “I was overwhelmed by all the support from my classmates, alumnae, board of directors and parents, and I wanted to do all I could to help the school be recognized.”
Over the next few years, Makayla did just that: She won lots of ribbons and was crowned high-point rider at nearly every IHSA show. Her parents were right there, cheering her on. She became part of Sweet Briar’s first National Collegiate Equestrian Association team in 2017, competing as the only Division III school against Division I schools. And each year, she’d always be just short of qualifying for IHSA nationals. But her Sweet Briar experience was about so much more than just ribbons.
“The riding program was always very supportive of me and helped me to emerge as a leader on the teams,” Makayla says. “Honestly, the skills I learned being a team leader have stuck with me the most.”
Nevertheless, when she rode to victory in May, it was a moment she had been waiting for her entire life.
“Winning the Cacchione Cup for me was like the fairy-tale ending to my college riding career,” Makayla says. “It truly helped me recognize that hard work and determination can pay off in the most incredible ways possible. I was ecstatic to finally have made it to the national final. It was three long years of fighting it to the bitter end and being just short of it each time. And when I was there, I just wanted to leave it all out there. In the moment, I just wanted to give the horse I was on the best ride I could, so that it would leave the ring more confident than it walked in. The overlying motivation was that I wanted to prove that Sweet Briar was still around and still relevant. That the attempted closure hadn’t shaken us in our renowned riding program. That was my motivation.”
Since her historic win, Makayla has been working as a wrangler at Bitterroot Ranch in Wyoming with her friend and classmate Courtney Barry, who found the job online — a dream job for both. When she’s done, she’ll head back to Germany to work for two months at the riding facility in Marburg-Dagobertshausen before she starts her first “normal” job in accounting back in the U.S.
“I think I am in a fascinating place in my life and career,” Makayla notes. “I have had wonderful opportunities, but also time to explore what I want to dedicate my time to. I will be exploring many more opportunities to decide which one suits me best!”
And who knows what might come next? Winning the Cacchione Cup has definitely given her an extra push. “It reignited my big fat dream of going to the Olympics — and believing in myself that I could get there with more hard work and determination,” Makayla says.
There’s no doubt in her mother’s mind she’ll find her way. It’s in her personality.
“She has always been an old soul and extremely comfortable in her own skin,” Jan says. “She doesn’t care what other people think. She does what she wants to do and doesn’t let anything get in her way. I think a lot of that, too, is Sweet Briar.”
This article first appeared in the Fall 2018 Alumnae Magazine.