Meet Your Neighbor: Sam Cockburn Talks Horses, Family, & the Future

Written by Kaitlin Hill

“I always wanted to ride. I started riding when I was 3,” shares Sam Cockburn, a familiar face in the local steeplechase and hunt scene.

For Cockburn, an inclination for equestrian sports runs in his blood. “My mother had a boarding and lessons facility in Maryland that she started with my grandfather. My grandfather always bred flat horses and steeplechasers.” His grandfather, Gordon “Gordie” Keys, was a household name in the equestrian world for the thoroughbreds he raised, owned, and raced. Cockburn adds, “He and my mom bred a horse named Iron Fist. He went off to win the Virginia Gold Cup and the My Lady’s Manor Steeplechase.”

He continues, “We’d sell them, they’d breed them, and my father would point-to-point them. Then they would sell to bigger stables.”

Cockburn’s father, Bay Cockburn of Shuckburgh, England, would have a legendary equestrian career in Virginia’s Hunt Country. Between 1988 and 1998, he participated in 433 steeplechase races resulting in 85 wins, 74 second places, and 54 third-place finishes. His career would be cut short after a paralyzing fall in 1998. He passed away in December 2013.

“I started foxhunting and doing shows when I was about 8, and [my dad] asked me if I wanted to start racing,” says Cockburn. “My first pony race was at the Rappahannock Point-to-Point.”

The Old Dominion Timber Race.

At 16, Cockburn would get his first horse. “My dad got me a horse from a local guy named Gregg Ryan, who is Master of the Piedmont Fox Hounds. I got to ride my first point-to-point at Casanova in 2009, I believe. And I won my first point-to-point race.” He adds with a laugh, “But then again, the next week, I broke my first bone at the Blue Ridge Point-to-Point. … I broke my left wrist on the second to last hurdle fence. So, [in] my first two weeks of racing against adults [I had] a win and then a broken bone.”

The injury didn’t put Cockburn off racing, nor did it dampen his dad’s encouragement. “I think my dad had me riding flat races before they even took the cast off,” Cockburn laughs. “Once they cut the cast down below my elbow, I was riding flat races at the point-to-points, to the dismay of my mother and the other jockeys.” He finishes, “But dad wouldn’t have it any other way.”

Like his father, Cockburn splits his time hunting and racing, enjoying each thoroughly. “He was a full-time huntsman and he only stayed an amateur jockey. He just liked to race. He was an adrenaline junkie.” Cockburn continues, “He was my idol. I grew up watching him; I would rewatch all his replays on VCR. So I always wanted to race. And, I’ve always enjoyed hunting as well. I love whipping in. I whipped in for Middleburg and Piedmont. I’ve also whipped in a little bit to Warrenton Hunt this past year. I love hunting, [and] I love the hounds. I think it’s a great thrill.”

He expands, “I think I get more satisfaction out of producing a racehorse, but I have more love for hunting. It’s something where I can just shut the world off and enjoy.”

Though perhaps what he enjoys most is the relationships he develops with the horses. This can take time, and patience. “My horse, Keys Discount, my grandfather and I got for $2,000. He is showing a lot of promise over timber fences, after a kind of dismal hurdle career. But, you know, perseverance. Stick through it.”

Sam on Keys Discount. Photos by Joanne Maisano.

He continues, “It takes a long time to produce a steeplechase horse. It’s very, very time consuming and you have to be patient. You have to let them have a bad season… You can have a great horse and you can have a terrible season that makes you want to throw in the towel. But sticking with it is a really rewarding feeling.”

He finishes, “If you are not in tune with your horses, you could be sending a horse off to lose. You have to be aware. They’ll run all day for you, but you have to set them up to win.”

On April 6’s Old Dominion Point-to-Point, Cockburn did just that with Keys Discount. He shares, “I was entered in the foxhunter division in the point-to-point circuit. That’s supposed to be just amateurs on their foxhunters, more of a nod to the tradition of steeplechase racing. I was the only one entered, so they combined me with another race with professional steeplechase horses that are being run to ride in sanctioned races.” He adds, “And, we beat ‘em. We beat them by a lot. So, it was a nice feeling.”

In mid-April, a trainer reached out to Cockburn to purchase Keys Discount. Cockburn shares, “I will enjoy rooting for him in the future.”

When asked about his plans for the future in the sport, Cockburn sagely says, “The future is always uncertain. It’s a very difficult lifestyle and difficult to make a living.” He continues, “Hopefully, one day down the road, I’ll grow a clientele and go off on my own.” For now, “You gotta stay healthy and take care of yourself,” and adds with a laugh, “and put the money away when you can.” Cockburn currently works with local trainer Julie Gomena. “She was very good to my father and she would let us school her timber fences and hurdles. So, I’ve always had a good relationship with her and started working with her full-time in the past year… I’m lucky to have Julia as an employer and as a mentor.”

Left: Cockburn and Julie Gomena. Photo by Joanne Maisano. Right: Cockburn with his mother, Chrissy Heard, and his sister, Katie Baker, at the Middleburg Fall Races. Photo courtesy of Sam Cockburn.

As for newcomers to the sport — either spectators or aspiring athletes — Cockburn says, “My advice is to go to the races. Watch the races. Watch how the horses are jumping. Watch how the jockeys are riding. Follow the horses through the point-to-point season and reach out to your local trainers.” He adds, “If you want to get into it, reach out to someone like myself, or Julie Gomena, or Neil Morris, who is local to Middleburg. Come see their facilities, ask questions. You just have to knock on doors, or send emails and Facebook messages these days.

“It’s not a secluded circle. People shouldn’t think that. We want people to be involved with it. If new people don’t come in, the sport won’t grow or it’ll eventually die. I would like people to know that it’s very open.”

Only 31, yet with the wisdom of a much older man, Cockburn says without prompting, “It’s not just showing up on race day. You get to be a part of your horse improving as an athlete, as an animal. You get to be surrounded by other people who love the sport. And you get to meet some of the hardest working people in the world.” He finishes with a laugh, “But if anyone tells you they know everything about a horse, they are lying to your face. You’ll never know everything about a horse because they are all different. Some horses will drop you one day and then win a race for you the next. It’s a rollercoaster.” ML

Published in the May 2024 issue of Middleburg Life.

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