The best vantage point for watching the Aiken Steeplechase Association competitions each fall and spring is the James Stainbrook Overlook, affectionately known as The Tower. It was built thanks to a generous donation from the financier, steeple- chase horse owner, and consummate equestrian whose name it bears.
It’s easy to spot James at the course — he’s the gentleman in morning coat and top hat, formal garb required when he was privileged to be invited into the esteemed Royal Enclosure at Ascot Racecourse in England for the 2015 Queen Elizabeth II Jubilee Stakes.
James’s story begins the way all good horse stories do — on the other side of a fence, staring longingly at something just out of reach. “When I was 5, we lived behind a horse farm. I’d sit on the fence post every day with a pocket full of sugar cubes, trying to convince the farmer to sell me a horse for 37 cents or whatever I had in my pocket. He never did. Then we moved and moved again — eight times before I went to college.”
There were no barns in the backyard or ponies waiting after school. But even as a child, James was captivated by the power and poetry of horses. His early obsession never entirely faded — it simply waited for the right moment to return.
FROM BALANCE SHEETS TO BRIDLES
Before James found himself immersed in the world of foxhunts and finish lines, he was making his name in finance. He began his career as a CPA with Price Waterhouse in Ohio before earning a Master’s of Tax degree and relocating to the Buckhead area of Atlanta, Georgia, just as the city was beginning to boom in the 1980s.
It wasn’t long before he made the leap from accounting to wealth management, eventually becoming Southeast Regional Director at Prudential-Bache Securities. He later founded his own financial firm, which he sold before retiring at age 50. Along the way, a windfall put a dream deferred in reach.
“I went to Wall Street, and my first bonus was three times my annual salary. I’d have been brain-dead not to take that opportunity.”
Rather than spend that check on cars or condos, he made a choice that would alter the course of his life: he went to Argentina, learned to ride by playing polo. At that time, he was matched against a talented 12-year-old, Adolfo Cambiaso, now a polo pro and breeder and possibly the biggest name in the sport. Even then, his skills were impressive, James recalls.
“I stayed long enough to learn to ride and play. Then I came back and joined the Atlanta Polo Club,” he says.
That decision — part romantic impulse, part calculated risk — reconnected him with the passion that had stirred in him decades earlier on that fence post. On his return to Atlanta from Argentina, he bought a string of polo ponies, deepening his horsemanship skills by riding them bareback. He boarded his horses at a farm owned by John McClure, who was heavily involved in foxhunting with the Shakerag Hunt. One morning, James caught sight of something unexpected — and irresistible.
“I saw a group of guys tear out of the woods yelling ‘Tally ho!’ with a flask in one hand and reins in the other. I said, ‘Whatever that is — I’m in.’” From there, he fell hard for foxhunting. He used his polo ponies — most of which weren’t bred for jumping — to follow the hounds across the Georgia countryside. Not all of them were up for the task, but one stood out.
“Only one of them could really jump, and that one saved my life more than once,” he says.
Foxhunting introduced him to a new network of horse people — trainers, owners, breeders — all of whom had some connection to steeplechase racing. It didn’t take long for him to get swept up in it.
FALLING FOR THE CHASE
James first tried steeplechase by leasing a horse from a well-connected friend in Camden, South Carolina.
“I’d go down, ride out, help condition horses. Then I bought my first horse. That was 35 years ago.”
One horse turned into two, then into more. He eventually purchased a farm in Alpharetta, Georgia, which was still rural enough to offer good riding country at the time. And with work, he was able to stay in Atlanta with his horses and only had to go to New York a few days each month.
“I could hunt four days a week back then. All my friends in the hunt field were involved in steeplechase. That’s how it starts. You spend enough time watching timber races and you say, ‘Why not me?’”
It was a gradual shift that grew from community, passion, and the thrill of watching a good horse fly over a timber fence. He was building a lifestyle.
After years of living the dual life of businessman and horseman and a stint traveling the world, James made a more permanent move in 2017. He relocated to Aiken, South Carolina, a town with deep equestrian roots and a thriving steeplechase culture. There, he threw himself fully into the sport.
“Two years ago, I said, I’m going to take this steeplechase seriously. Last year’s Aiken Spring Steeplechase had 35,000 people. It’s the largest sporting event in South Carolina outside USC football. It’s bigger than anything else within 200 miles — except the Masters Golf Tournament.”
But for James, it wasn’t just about the crowds or the spectacle. It was about the horses and what the sport could offer them.
“We have 20,000 thoroughbreds born every year. Very few of them make it on the flat track. Steeplechasing gives them a second chance. They go from six furlongs to two miles. And if they’re still sound after that, timber racing — four miles and up, over stone walls and telephone poles. If they can do that, they can carry a flask without spilling a drop. That’s a good horse.”
BETTING ON JOY
James now owns six horses spread across Aiken and Camden in South Carolina and in Maryland and Virginia. Most recently, he bought into his first racing syndicate — a leap into the world of young prospects and longterm dreams.
“Buying a yearling is a leap of faith. But I did it so I’d have an excuse to spend mornings at the training track here in Aiken. I wanted to sit on the clocker’s stand, sipping coffee, watching them work through the fog. Then go to the Track Kitchen and lie to each other. That’s the dream.”
It’s not about trophies or earnings. It’s about ritual and the satisfaction of watching a Thoroughbred exercise in the morning, emerging from the mist on an early morning on the track. It’s about the time-honored tradition of equine activities. James's racing silks come with a history — and a little royal flair.
“My first trainer, Gerald Oxley, was English. He won the Queen’s Cup five times. He calls me one day and says, ‘A friend — some duke or other —died without an heir. His silks are being retired. Do you want them?’ They were hunter green with white seams. Simple. Elegant. I said yes before he even finished describing them.”
Of all the horses James has owned, none had quite the impact of Famous Amos — a horse that taught him how to take a jump and trust his partner in the field. If Amos couldn’t jump a fence, he would climb it — a testament to the horse’s dedication to the sport.
“He belonged to Jim Henderson, a hunt master in Atlanta, who had to retire. Amos was in his teens, but he became my hunt horse. He never refused a jump — not once. I closed my eyes going over some fences, but he got us there. I had him until he was a week shy of 35.”
Being deeply involved in the horse world is about the relationships with these extraordinary creatures, who are simultaneously powerful, fragile, and costly. Some might ask why James invests in a sport that rarely pays back in cash. His answer is simple.
“Nobody makes money in horses,” he says. “You know the old joke: If you want to make a million in racing, start with two. But that’s not the point. I do it because it gives me joy. I love being around horses. I love watching them move. That’s enough.”
