BY SARAH WELK BAYNUM

Charles Hairfield may be newer to the racehorse industry, but he is far from new to the Thoroughbred breed and the horse world.

His love of horses started at a young age on Seabrook Island, in South Carolina, where he has been boarding his horses since age 11. Today, he is the barn’s manager and a United States Hunter Jumper Association certified trainer. 

But Hairfield has always felt a special connection to the Thoroughbred—which provided him a path to the Florida racing and breeding industry. 

“I was always drawn to the Thoroughbreds because of their heart over the warmbloods all day. Yes, warmbloods are big, beautiful, fancy, and sometimes arguably better for the hunter ring. But for me, I always loved the Thoroughbreds. That’s why Thoroughbreds have always been part of my training, part of my career, and part of my client’s journeys,” Hairfield said. 

It’s no surprise Hairfield also found success at the 2020 Retired Racehorse Project’s Thoroughbred Makeover.  

“You get to see [Thoroughbreds] do hunters, jumpers, dressage, polo, cross country, ranch work, barrel racing, etc. It really puts into perspective how not only are these horses extremely well-bred athletes to run and to race, but they have a ton of ability to do so many things. [Thoroughbreds are] unlike other breeds, which are typically suited for just jumping or dressage, for example. It was very special to be in that environment and be able to see so many of these [Thoroughbreds] having second careers.”

Hairfield took two horses to the 2020 RRP—his Still Dreaming and New Vocations graduate Win the Shake for a client. 

“I was fortunate enough to place first in my round and make the top five in the RRP show hunters division with [both horses],” Hairfield said. 

But it was Hairfield’s mare Glassy Aly, by Breathless Air, who introduced him to the racehorse world. Winless in two starts on the track, Glassy Aly had a successful second career as a hunter jumper. 

“I’ve had a variety of students that rode and competed Glassy Aly. She even made it on the cover of The Carolinas Equestrian,” Hairfield said.

However, Glassy Aly could make things challenging for Hairfield’s students. 

“She was opinionated, but she had heart. She wasn’t just going to do it for you—you had to earn it. You had to be worthy in her eyes and you weren’t going to get on with an ego and agenda. You had to listen to her, and you were going to have to feel her. But that’s hard with kids, riding students and people that are wanting to show and care about the ribbon.”

Hairfield then began to think about Glassy Aly’s future differently and considered breeding her to Thoroughbred stallions in Florida for racing.

“I thought, you know what? That mare is such an athlete—let’s see if I can breed this horse instead,” he said. “This way, I’m also going to breed my own future RRP horse. I do a lot of sales, but only in special and unique situations, because I care where the horses end up. And with Glassy Aly, it was almost like I had a feeling about breeding her and I wanted to see it out.” 

With advice and help from trusted friends in the industry, Hairfield began the process of breeding Glassy Aly in Florida. 

“Today, I now have two young racehorses out of her that are still in Florida. One is a 2-year-old and her name is Valiant Jane. She is named after my deceased aunt, who is the reason that I got into horses to begin with. My aunt was a national Arab trainer,” Hairfield said. 

Valiant Jane is by Bridlewood Farm stallion Valiant Minister and Glassy Aly’s 2023 colt is by the late Florida sire Uncle Chuck.

Valiant Jane is currently in training with Paul Watson in Ocala.

“Since I’ve had [Valiant Jane] here for training, she’s grown a lot,” Watson said. “She was also a little bit backward when she first came to me, but she’s since grown to 16.1 hands. She’s had three or four nice breezes and she’s really shown me some talent.”

That talent and time that will determine whether Valiant Jane will provide Hairfield the same success in racing he has had with hunter jumpers.

Return to the August 27 issue of Wire to Wire