WinStar Farm reached out to Hall of Fame equestrian and Olympic medalist David O’Connor ahead of this weekend’s Defender Kentucky Three Day Event at the Kentucky Horse Park, hoping for a few pictures of the five-star contender Phelps so that the famed Thoroughbred stallion and breeding farm could follow along with this weekend’s action.

Phelps, an 11-year-old unraced gelding, was sired by WinStar’s two-time Breeders’ Cup Classic winner Tiznow.

“They have the exact same eyes,” O’Connor said. “I got to visit with Tiznow about a month ago, and I guess he’s also a funny horse to be around. He has the same look in his eye that Phelps has.”

Known by The Jockey Club as Tiz Special, Phelps was bred in Kentucky by Fred W. Hertrich III and John D. Fielding out of the Cactus Ridge mare Boom Town Gal. However, the gelding never showed any aptitude for racing, and never recorded an official workout.

Joanie Morris was given the gelding, then “sold” Phelps to O’Connor as a resale project when the gelding was a 3-year-old. The price? $1.

That’s a pretty good deal for a horse who is now taking on his second start at the top level of three-day eventing, and was the only one to finish inside the time at the Maryland Five Star last fall.

“We laugh about that a lot,” said O’Connor. “I was going to give her part of the money when we sold him, but we just never got around to that. Earlier today, she joked that she’s ‘Getting famous off a bad debt!’ But now she’s a big supporter of [rider] Mia [Farley], and we’re all enjoying the journey.”

O’Connor, an individual Olympic gold medalist and member of almost every U.S. Equestrian Team from 1986 until his retirement in 2004, said he specifically looked for Thoroughbreds after his retirement because of their good brains and trainability.

“I just love their minds,” he said. “They’re smart and trainable, and when they understand something they really understand it. I love watching them gallop. They have a bad reputation for being difficult, but they’re trained when they’re young to give 110 percent all the time, and now we don’t need that. So then once they get it, they really get it. You don’t have to tell them over and over again.”

Phelps is a prime example of that, O’Connor said.

“He’s so enjoyable to be around. He doesn’t get excited, doesn’t get nervous. Today at the [Kentucky] Horse Park, there were other competitors walking past him with really excited horses, and he’s just wandering around on a loose rein, eating grass.”

Phelps spent his first six months away from the racetrack primarily living outside and occasionally being ridden in the paddock.

“We restarted him our way, and when he did his first tiny little event, he was just very simple,” O’Connor said. “I didn’t know how athletic he would be, and he wasn’t that great of a mover, but he just kept on giving us more.”

Two years after O’Connor brought Phelps home, he invited a young rider from the West Coast named Mia Farley to come train at his farm. O’Connor suggested she take on Phelps as a project horse. Farley competed with Phelps at novice level in 2019, and had moved him up to the two-star level by the following summer.

“He kind of just kept going up the levels,” said O’Connor. “Mia’s done a fabulous job with him over the years. After the first couple times at the preliminary level, we could see that it wasn’t hard for him; he just understands it. I guess I never really thought he’d be at this [five star] level, but he just kind of keeps doing it really easily.”

The only thing that isn’t necessarily easy for Phelps is the sport’s final phase, show jumping. In his first foray at the five-star level, last fall at Maryland, Phelps’ speedy cross country round moved him up to third place before the final phase. On Sunday, however, Phelps knocked two rails in the show jumping and wound up finishing fifth.

“He’s getting stronger,” O’Connor said. “A Thoroughbred jumps slightly differently than the typical warmblood; they jump more off their front end. He wants to be careful, but he needs to have the shape to be able to do it. He’s a professional’s ride, in that sense. He’s not hard to ride, but to be clean, he needs to be in the exact right place at the jump and be in the right rhythm. Luckily, Mia is good at that!”

Phelps and Farley will compete in the first phase, dressage, this Friday at 1:24 p.m. Eastern, and are scheduled to contest the second phase, cross country, on Saturday at 2:50 p.m.

O’Connor said that watching his horse compete at the top level is a thrill unlike anything he felt in the saddle prior to his retirement.

“I really do enjoy being part of Mia’s career,” he said. “It’s another special level, and it’s nerve wracking because you really want it to go well, but supporting these riders is a great joy of mine.

“The cross country course at Kentucky is more technical than what he saw last year at Maryland, but I think that was one of the hardest five starts that I’ve seen in a number of years. We know now that it is within his capabilities, whereas last year we were hoping that he was capable. If she can give him a good ride and have a good plan, well, anything can happen out there.”

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