In recognition of Wednesday’s 60th birthday of Phillip Dutton, who since becoming an American citizen in 2006 has been a stalwart of U.S. eventing teams, representing the U.S. in four of his seven Olympic appearances (Hong Kong 2008, London 2012, Rio de Janeiro 2016 and Tokyo 2021), winning individual bronze in Rio, we’re looking back to our report on his first win at the four-star (now five-star) level, which happened at the 2008 Rolex Kentucky Three-Day Event on Connaught, the horse with whom he went on to compete on the Hong Kong Olympic team.

For so many years, Connaught took a back seat to the limelight of Olympic gold medalists and three-star winners in Phillip Dutton’s stable.

But almost nine years after arriving at True Prospect Farm in West Grove, Pennsylvania, Connaught achieved something that Dutton hasn’t claimed with any of his many talented mounts—a victory at the four-star level. When Bruce Duchossois’ Irish Sport Horse topped the Rolex Kentucky CCI4* by almost 6 points, he confirmed his spot as one of the world’s best horses in front of a record crowd of 103,521.

His clean show jumping round—one of just two all day—edged him ahead of Becky Holder and Courageous Comet, who’d led the event in Lexington, Kentucky, April 24-27, from the start.

The win added to an illustrious past few years for the phenomenal jumper, who finished second at Rolex Kentucky last year, after representing Australia at the 2006 World Equestrian Games. Dutton now rides for the United States, and Connaught will be a candidate for the Olympic Games, although Dutton has three other prospects in The Foreman, Truluck and Woodburn (who finished 10th at Kentucky).

But not every rider would have gotten Connaught to this victory. “He’s taken a while in all areas,” said Dutton with his typical understatement. “He was hard for me. And because he goes so high over his fences, [cross-country] was hard on him. He gets tired.”

In 2004, Connaught fell at Kentucky at the Sunken Road. “He jumped into the bounce, put a stride in and stepped back [off the bank],” Dutton said. “It was a horrific fall.”

Dutton, undeterred, built a sunken road at home. “It was the up and down part he was having trouble with,” Dutton said.

When Connaught returned to Kentucky in 2006, his first trip back since that fall, Dutton said he was quite nervous about the Sunken Road.

“I was a fraction lucky that year [at Kentucky], although he jumped a hard one [at the 2006 WEG] well,” Dutton said. That year, “Simon” finished fourth at Kentucky, and he returned in 2007 to take second.

Because of Simon’s huge, lofty jump, he puts more wear and tear on himself, and, as a result, Dutton said he doesn’t do a lot of big courses with him every year. “I might take him intermediate. Last year before Kentucky I did one course, and this year I did two,” he said. “He does try so hard.”

Dutton said that Simon’s successes have also come from some management changes. “It’s always been hard to keep weight on him,” said Dutton of the 15-year-old gelding (Ballysimon—Bromehill Rogue). “He’s naturally very lean, and sometimes he’s been too skinny. He likes his alfalfa hay, and it’s good for his stomach. We also keep him out as much as we can on grass.”

Simon doesn’t travel well, and Dutton has started shipping him loose in a box stall to make him happier.

“A lot goes into the care of Connaught,” he said with a laugh.

“It’s very rewarding because he has not been an easy horse,” he added. “He’s super talented, but a lot of people have put a lot of effort in, and Bruce has been very patient. Persistence is the key. We’ve stuck with him and had faith in him.”

Better To Win

Dutton said the five times he’s finished as runner-up at Kentucky haven’t bothered him at all. 

“It feels a lot better to win, but I haven’t been too worried that I haven’t won,” he said. “I’ve been lucky to be second several times, although there was one year with True Blue Girdwood when I had one rail and could have won.”

In the past, he said, he was always trying to catch up with the dressage leaders, and this year he thinks the improvement in Connaught’s dressage, which had them standing in third place going into cross-country, gave them a better chance. He attributed some of the improvement in his score to a comment his wife, Evie, made as he was warming up for dressage.

“She said, ‘You’re pushing too much. Don’t try so hard.’ I slowed it down, and he goes in the ring, and the energy goes up a notch anyway. So I rode quiet and relaxed, and when we went into the ring, that added a bit to it,” he noted.

That comment proved to be a worthwhile bit of insight from Evie’s point of view, since Dutton said he will be giving her the Rolex watch he won. “I’m rough on my watches—I’m always banging them up,” he said. “It will look much better on her.”

Duchossois usually can’t watch Dutton on his mounts at Rolex Kentucky, since the date interferes with a horse show he helps run in his hometown of Aiken, South Carolina, but this year he wasn’t affiliated with the show and traveled to Lexington.

“It’s probably the highlight of my horse career—in racing, riding, eventing or anything,” said Duchossois of his win. “It was the thrill of a lifetime.”