Teddy and his horses split their time between Florida and New York
By Lindsay Brock
Portraits by Lindsay Brock and Simon Stafford
When asked what they want to be when they grow up, not many boys from the middle of Queens in New York City, New York, come back with the answer, “a horse trainer.” Theodore “Teddy” Demetriou, 42, recalls that his earliest response to that ever-popular question was “a professional baseball or basketball player.” But that all changed when he met a pony and sat in a saddle for the first time.
Teddy with Louisiana 7 at Wolver Hollow South in Wellington, Florida
Teddy may have grown up as a city kid in Queens, but his family often retreated from New York City to their small second home on Long Island’s North Fork. A mile up the road he lived on was Hidden Lake Farm, owned and operated by trainer Jackie Bittner. Nestled between sprawling fields, Hidden Lake Farm was home to one of the most popular riding schools in Long Island and the place where Teddy took his first lesson at 4 years old. According to Teddy, that first lesson started it all.
Many lesson barns are teeming with pony-crazy little girls, but Teddy stumbled upon Hidden Lake Farm at a time when the program included several competitive young boys. While Teddy’s familial influence centered around mainstream sports, his friends at the barn nurtured his pony jock identity. Teddy’s parents — Peter, a collegiate athlete and founder of the family’s insurance agency, the Demetriou Group of Manhattan, and Irene, a fellow animal lover like her son — immediately supported their child’s interest in horses.
Long Island’s North Fork is steeped in foxhunting history, which led Teddy to foxhunt on his first pony. The mount was a 12.1-hand black Shetland pony named Porky that was influential in sealing Teddy’s destiny in horse sport. Teddy continued riding and foxhunting in North Fork into his teenage years.
As a child Teddy thought he would be a baseball or basketball player when he grew up but that all changed when he met a pony and sat in a saddle for the first time.
Equine Influence
Teddy played high school sports, won a state championship as captain of his baseball team in 1994, earned a management and marketing degree from Long Island University and was even asked to play professional basketball overseas for a time. But while some riders grow out of their pony-crazed days and move on from horses, Teddy never did.
“When I was 13, we went to try a hunt horse in a small indoor ring in Hauppauge, New York,” said Teddy, who was the first person in his family to ride and compete. “That’s when I met Ralph Caristo. I didn’t know it then, but he would become like a second father to me. He taught me so much about riding, training and horse dealing. When I was 14, Ralph took me to Junior Hunter Finals on a horse he found for me called Another Legend. He then found me equitation horses, and then jumpers, and my entire career snowballed from there.”
It was on a trip to Europe to compete on the Sunshine Tour in Spain when he was 19 that the pieces started to fit together for Teddy. “I began to learn how horses develop, and that in the beginning they all start in the same place,” he said. “It sparked an interest in me for developing young horses.”
Teddy had many mentors along the way, which helped him develop into the rider and trainer he is today.
Teddy’s involvement in the immersive community that is horse sport eventually inspired other members of his family to ride as well. His younger brother, Michael, rode for a time before taking over the family’s insurance business, and his sister, Chrisanthi, was competitive in the equitation ranks, riding with Andre Dignelli’s Heritage Farm and taking over Teddy’s mounts when they stepped down from the top level. Teddy’s father also took up foxhunting and was later named master of the Smithtown Hunt.
“When I was riding with Ralph, he bought a 5-year-old for my father to hunt on called Main Sail,” said Teddy. “He was a grey Irish gelding that would not hunt! Ralph and I, along with Ron Esposito, who worked for Ralph at the time, took on the job of getting the horse into the show ring as a jumper. I competed Main Sail at the first Marshall & Sterling League Finals in Poughkeepsie, New York, and five years later went to the North American Young Riders’ Championship in 1996 with him. It was my first time developing a horse from the children’s jumpers to the low juniors to the highs and then young riders.”
At 21 years old, Teddy began working with U.S. Olympic team silver medalist Peter Leone and his two brothers, Mark and Armand. This legendary trio furthered the young equestrian’s zeal for being involved with top sport.
“They were like family to me for a very long time,” Teddy said. “They had three very different ways of getting it done, but they were all so good at what they do.”
Teddy competing Conntador at the Vermont Summer Festival
Going it Alone
Teddy combined all the influences in his life to form his own business in 2000 at the age of 23. Carrying the moniker Wolver Hollow after the road he used to gallop ponies down on Long Island, Teddy runs a training business at his 42-acre farm in Chester, New York, just 55 miles north of Manhattan, as well as a farm in Wellington, Florida.
“I think because my family’s business is selling insurance, I always had a knack for sales; maybe that’s why I got along with Ralph so well,” Teddy recalled. “My father was also such a huge influence on me. When I was riding horses as a teenager, he and Ralph teamed up to sell them so we could buy new ones. I always knew it could be a profession, but I was very fortunate my parents were so supportive.”
When asked about Teddy’s growth in the industry, Ralph recalled him being a “sponge” from the moment he met him. “Teddy was my shadow when I was selling horses, learning as much as he could and absorbing all that he could to make him a good all-around horseman in every way,” Ralph said. “And that’s exactly what he became.
“He was always a very good student and wanted to learn and experience the horse show scene,” Ralph continued. “Our families were very close and we all spent a lot of time together — it was a nice time in both our lives, watching him grow and mature into a terrific rider and trainer. I’m very proud to see where he is today and to have watched his success grow from the time he was very young.”
Teddy named his farm Wolver Hollow after the road he used to gallop ponies down on Long Island.
While Ralph was a mentor in the horse world, Teddy turned to his father as a sounding board when starting his own business. His father passed away in 2005, but Teddy used his wisdom to help shape Wolver Hollow into the sizable training, sales and competition operation it is today.
“Starting your own business is scary and I second-guessed myself a lot at first,” Teddy admitted. “I always had my father behind me. I think any young adult already knows how their father will answer the questions they ask, but you need to hear it in their voice as reassurance. I was lucky to have that.”
The Hills of Vermont
When asked what his strongest talent is, Teddy is quick to respond with “matching horses and riders.” This self-proclaimed match-making ability was proven true during the 2017 Vermont Summer Festival in East Dorset, Vermont. A longtime visitor to southern Vermont for the competition that began more than 25 years ago, Teddy was drawn to the Vermont Summer Festival as a perfect venue to introduce new horse-rider combinations.
In July 2017, rising star Matthew Metell rode to his first grand prix victory under the tutelage of Teddy aboard a mare they had just imported from Holland. Matt, now 29, started riding with Teddy when he was 15 and finished second in the 2008 Platinum Performance/ USEF Show Jumping Talent Search Final – East. He later began working with Teddy in a more professional capacity, which is when he began looking for a horse to call his own.
Together, Teddy and Matt found Donchalant, a 9-year-old Dutch Warmblood mare (Larino x Amaretto I). Teddy had his eye on the mare since she was a 6-year-old being ridden by Portugal’s Rodrigo Silva Morgado.
“Matt and Donchalant were, and still are, great partners,” said Teddy. “Watching them win their first grand prix together just a month after we imported the mare was really special for me. The atmosphere at the Vermont Summer Festival, with a supportive spectator turnout, really helps horses get used to competing in front of a crowd. That win set them up for success at the top level.”
Helping Matt get his start was one way Teddy paid it forward in the horse world, by helping another young professional find his niche the same way Ralph had taught him.
“The most beneficial thing about working for Teddy was getting the experience of going to Europe and shopping for horses,” said Matt, who recently started his own training business. “He taught me a lot about that process and how to go about finding horses that way. Working for him provided me with a lot freedom to figure things out on my own. That freedom was a positive for me because I could do a lot of the aspects of owning your own business myself before it was time to go out on my own.”
During summer 2019, Teddy will return to Vermont with a string of up-and-coming horses and riders in all three rings. Additionally, Teddy’s team is expanding and will feature young talent Cooper Dean as rider and trainer.
While his competition horses are excelling in the ring, Teddy’s business is always growing. Currently, he owns between 20 and 40 3- and 4-year-olds with anywhere from 10 to 15 sales horses available at one time.
“The sport has changed so much over the years,” said Teddy. “I feel like every five years you need a different kind of horse to jump the courses that are being built at the time. I look for ridable, smart, brave and scopey. Horses have to be the total package nowadays. They can’t just do one or two things very well; they have to do five to 10 things very well because of the questions that are asked on course.
“My job is to stay ahead of that curve,” continued Teddy. “It’s a challenging and ever-changing business, but it’s what I was born to do. No matter the challenges, I consider myself so lucky to be able to continue the legacies of the many people who helped me along the way and do what I love for a living.”
For more information, visit wolverhollowfarm.com
Photos by Jump Media, www.jumpmediallc.com
