Rutledge Farm, Middleburg, Virginia
How long have you been part of the horse world?
I’ve been involved with horses my entire life. I rode my first horse, a Shetland pony, at Pegasus/Meadowbrook in Washington, D.C. when I was 6 years old. When I was 16, I had the privilege of training with an up-and-coming young rider, now a lifelong friend and Olympic gold medalist show jumper, Will Simpson. My love for the sport only grew from there when I picked up polo the following year. My late stepfather, Hermen Greenberg, was an avid Thoroughbred owner and breeder. A prior president and long-term board member of the Washington International Horse Show, he was inducted into their Hall of Fame in 2009. Plus, my wife, Sandra, is a show hunter.
What part do you play in the horse world?
In 2015 I took over my late stepfather’s Thoroughbred racing and breeding operation, known as Rutledge Farm, whose main house was built in 1740. We converted it to a sport horse facility and made a number of improvements, while making sure to preserve the farm’s deeply rooted history. We opened up our property to local hunters and show jumpers, and we have five barns, 35 stalls, indoor and outdoor arenas, a lunging arena, a derby field, a polo field, and 19 paddocks, all located just minutes away from Middleburg’s historic city center.
Tell us about the Rutledge Farm Sessions.
Will Simpson visited me at Rutledge Farm in 2017, and shortly after arriving, we decided it would be fun to host a clinic for a few local riders. Everyone had a great time, and that was the day the Rutledge Farm Sessions were born.
We expanded in 2018, when my friend Mike Smith introduced me to McLain Ward in Wellington, Florida. McLain was planning to be at the Upperville Colt & Horse Show and agreed to host a clinic, as a part of our series, while he was in Upperville. We finished up our first full year of the Rutledge Farm Sessions with Leslie Burr-Howard, Phillip Dutton and Will Simpson. In 2019, we expanded to offer clinics for more disciplines, including dressage and equitation. We hosted Peter Wylde, Will Simpson, Phillip Dutton, Debbie McDonald, Ali Brock, Stacia Madden and Boyd Martin that year. It turned into a really amazing experience, being able to include so many Olympic medalists, top athletes and trainers to teach equestrians of all ages and skill levels.
This past year was a challenge, as it was for everyone within our community. We adapted the Rutledge Farm Sessions to offer virtual training with Boyd Martin, and we were fortunate enough to be able to safely host two sold-out clinics in the fall with Anne Kursinski and Sandy Ferrell. So many wonderful relationships have made the Rutledge Farm Sessions possible over the years. We are so grateful for all of our partners, like US Equestrian, and our local five-star equestrian resort, Salamander Resort & Spa.
What’s your biggest achievement?
Taking Rutledge Farm to the next level, being able to convert it into a top sport horse facility and putting it on the map internationally. We are very proud that everything Rutledge Farm offers is always and only first-class and at the highest level. When we designed footing for our arenas, we even hired Attwood Equestrian and consulted with Will Simpson, to ensure that our footing would make any Olympic gold medalist happy. It was also fun to revive and use Rutledge Farm’s polo field, which hadn’t been used for over 50 years.
What are your goals for the future?
To play more polo! I also want to refocus my energy on a few consumer-packaged goods that I am a part-owner in.
What’s the best thing about your life?
My wife, my family, my friends, my horses and my dogs. I am astounded by how amazing my friends are, and I feel privileged that they consider me their friend. Having welcomed my son, Maverick Preston James last July, I watch him playing in his nursery and it awes me to consider how many children have called Rutledge Farm their home since 1740, and how different life must have been for them. I hope that they looked around the farm and felt as blessed as do my wife and I.
Best-kept secret about you?
My wife says I’m a great singer. Another fun fact is that my best man, the late Preston Madden, was 43 years my elder and bred the 1987 Kentucky Derby winner Aly Sheba.
Aleco, right, talks with Olympic eventer Phillip Dutton during a Rutledge Farm Session.
Photo by Allyson Lagi