Archive — this site is preserved as it appeared on 2026-10-26. No new content is being added.

Pan American Glory for Karen O'Connor and Theodore, World's Bravest, Most Beloved Event Pony

· By Patricia Vos · From pages 1, 33 of the print edition

The XV Pan American Games took place July 13-29 in Rio de Janeiro, Brazil, featuring 5,500 athletes from 42 countries competing in 28 different sports. The US delegation was made up of nearly 600 athletes and they brought home an impressive 237 medals with the US leading the final medal count, not-so-closely followed by Cuba and host nation Brazil.

But does anyone from Middleburg pay much mind to medal sweeps in synchronized swimming or table tennis? Unlikely. Not to take anything away from the Herculean efforts of the judo team or the swimmers or badminton players who came home with the gold, but our concerns tend to run with all things equestrian.

Lucky for us then that the equestrian event squad, a decent percentage of whom were locals, came home with a small pile of medals, including a few for The Plains resident and eventing star Karen O'Connor who rode a pony, yes a pony, to double gold medal glory.

If an event horse always strikes one as a particularly brave creature as it approaches daunting ditches, banks and solid obstacles, imagine how plucky a 14.1 and a bit pony appears as it does so. Theodore O'Connor, the 12-year old Thoroughbred/Arabian/Shetland cross, is now quite possibly the bravest, most beloved event pony in all the world.

While getting a pony to an international event is never a sure thing, the purported troubles at the Rio venue nearly made it a non-starter for the entire squad. As the team was being selected, prepared, trained and beginning their travels with a trip to Miami for quarantine, word from Brazil was not encouraging. The cross country course building was behind schedule. There were health concerns. The dressage teams that had traveled ahead for their competitions reported back with stories of nightmarish bureaucracies.

Back home, veterinary concerns over two of the horses chosen for the US Event team forced last minute changes to the squad. When, at last, they left for Rio, the US team was comprised of Phillip Dutton of West Grove, PA with Truluck, Gina Miles of Creston, CA with McKinlaigh, Stephen Bradley of Leesburg, VA with From, Mara Dean of Round Hill, VA with Nicki Henley and Darren Chiacchia of Springville, NY with Better I Do It.

The troubles and tribulations leading up to the competition were soon put aside however once the first phase of the competition began. The US team completely and totally swept up in Dressage taking the top five spots. Mara Dean led the field with 40.20 penalties, followed by Stephen Bradley and the 15-year-old Russian Thoroughbred From, then, Karen O'Connor and Theodore O'Connor (aka Teddy, Connor, Super Ted), Chiacchia and the 14-year-old Swedish Warmblood, Better I Do It, and finally, Phillip Dutton, at his first international competition riding for the United States, in fifth on Ann Jones and Shannon Stimson's ten-year old Thoroughbred, Truluck.

The one minor disappointment for the team that day was handed to Miles and the rather large McKinlaigh, a 17.3, 13-year old Irish Thoroughbred owned by Laura Coates and Thomas Schultz. An over-exuberant presentation in the arena left them in 11th place. Miles did not let that dampen her drive however and she and her decidedly unpony-sized mount went out the next day and came back with a clear and fast cross-country run.

Fellow members Dean and Bradley did not have such luck. Dean, leading after her stellar dressage performance the day before, pulled up on course when she suspected her horse had injured himself, a suspicion later confirmed by the team veterinarian. Bradley in the meantime had an unfortunate stop at the second water jump thus dropping him from his second-place perch.

One would like to say Dutton and Truluck enjoyed a typical Dutton cross country experience (as he is known for impressive runs) but "enjoyed" was not how he typified his clean run in interviews afterwards. Dutton apparently felt the course rode tougher than it walked and regretted that he and his horse never settled into a steady rhythm. Still a clean run being a clean run he moved up into second place after cross country, right behind O'Connor and Teddy.

That pair had gone out first on cross country and blazed across the three-star track without issues, gathering more and more Pony Power fans as they went along. They managed a run free of jumping penalties and with just a few seconds over time, Super Ted went to the final phase, Stadium Jumping, in the lead. And there they remained.

At the end of the final phase it was Team USA with the gold medal, Karen O'Connor also winning the individual gold, Phillip Dutton with the individual silver, and Gina Miles with the individual bronze – an impressive sweep not seen in 20 years at a Pan Am equestrian event. The Canadian Team took home the team silver while the Brazilian team pleased its raucous home town crowd with the bronze, thus qualifying both those teams for the Hong Kong Olympics.

While Teddy's fame and popularity were building with the eventing crowd leading up to his gold medal win in Rio, it now seems to have bubbled over to horse (and pony) lovers across the board. It was recently announced by Breyer that the super pony would be amongst their latest new portrait models.

Few would have thought it physically within the realm of possible for a card-carrying pony to win an international event. Certainly Karen O'Connor believed. As did his breeder, and original trainer and owner, P. Wynn Norman of Sportponies Unlimited. Understanding that this pony has many more places to go and the will and the wherewithal to get there, she has now opened up his ownership to syndication (The Theodore O'Connor Syndication LLC) in order to ensure his international competition dreams, and those of all his amazed and astonished fans, can continue to come true.