A Rolex Rookie Defies the Odds with her Off-the-Track Thoroughbred

Libby Head, a college student, completed the 2014 Rolex Kentucky CCI**** on her ex-racehorse Sir Rockstar.
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Libby Head and Sir Rockstar at the 2014 Rolex Kentucky CCI**** | © Kate Light

Libby Head and Sir Rockstar at the 2014 Rolex Kentucky CCI**** | © Kate Light

How many riders dream of galloping across the hallowed bluegrass at the Rolex Kentucky Three-Day Event? And how many accomplish the feat on an off-track Thoroughbred while pursuing a college degree?

Libby Head, a 23-year-old animal-science student at the University of Georgia, checked a big box on her bucket list last year when she completed the Rolex Kentucky CCI****.

She did it on Sir Rockstar, a 17-year-old, 15.2-hand Thoroughbred gelding who failed as a racehorse but found his stride as an eventer.

It all started when Libby met “Rocky,” a then unruly 10-year-old who had
raced 16 times under the Jockey Club name Sir Rock.

“At the time, I had another horse I had been going Training level on who just didn’t want to jump anymore, so I was looking for something else to show,” Libby says. “I was uneducated and I didn’t know much, so I didn’t realize how much talent Rocky really had.”

Libby and Rocky quickly moved up the levels together, winning CH-Y** team gold for Area III at the 2011 North American Junior & Young Rider Championships. That’s where she met Kyle Carter, Area III team coach and Canadian silver medalist at the 2010 World Equestrian Games.

“In the beginning, we struggled in the dressage just to get a qualifying score to do a CCI*** event, so when it finally started coming together, Kyle mentioned Rolex as a possibility,” Libby says. On track to graduate in the spring of 2014 with her undergraduate degree, Libby knew it would be difficult to handle a full course load while preparing Rocky for their biggest challenge yet.

“My parents, John and Sara Head, were nice enough to let me take a semester off to go to Kyle’s base in Ocala, Florida, to train, and I’m really glad I did that,” Libby says. “It was hard enough to just focus on preparing for Rolex.”

As a “Rolex rookie,” Libby tried to keep her expectations tempered. “I went into it just wanting to make it through, and I didn’t have any pressure,” she says. “It was my first four-star, so I wasn’t expecting to win. It helped me to keep my head and ride effectively.”

Libby and Rocky scored 63.8 in dressage, and then it was on to cross country, their strongest phase. The course caught out many experienced pairs, but Rocky and Libby jumped clear with 7.6 time penalties. “He makes it easy, and he loves what he does,” she says. “I just had a lot of fun, and how could I not? He just loves to jump, and he did everything I asked. I think he reads my mind sometimes.”

The clear cross-country trip moved Libby from 43rd up to 28th place. And in show jumping the next day, Rocky rose to the occasion once again, jumping one of just 10 rounds clear and inside the time to finish in 19th place.

Now Libby is back at school as a fifth-year senior, finishing her animal-science degree and riding on UGA’s eventing team. She balances school and a busy show schedule with Rocky and her second horse, a 6-year-old mare, Bocce.

“Time management is a huge factor, as is planning ahead,” Libby says. “I always set my school schedule first, and then I plan my show schedule around it. I can definitely be guilty of putting riding before school, as I’d rather let my grades suffer than my riding.”

But Libby has maintained a 3.0 grade point average to keep her HOPE Scholarship, which pays 50 percent of her tuition and is available to Georgia residents who show academic achievement in high school. She plans to graduate this month.

Libby and Rocky will face their next big challenge when they travel to Germany to compete at Luhmühlen CCI**** in June. She’s making the trip thanks to the $10,000 Essex Grant from the United States Eventing Association as well as support from her parents and a fundraiser held by the UGA eventing team.

Though her life currently revolves around horses, Libby says she’s not sure which direction she’ll take after graduation. “I would love to compete and train professionally,” she explains. “I’ll either end up using my degree to get a ‘real’ job or find some way to make it work in the horse business.”

Whatever she decides, Libby will always take with her the memory of defying the odds as a Rolex rookie with a little off-track Thoroughbred who exceeded every expectation.

This article originally appeared in the May 2015 issue of Practical Horseman.

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