Leaps & Bounds

Kent Farrington grew up without privilege in inner-city Chicago, yet RIDING HIGH forged his way to the summit of a sport often considered a special reserve of the elite. Robin Barwick caught up with him in the heart of the British establishment, at the Royal Windsor Horse Show...

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Windsor Castle has stood on high ground above the River Thames for more than 1,000 years. Commissioned by William the Conqueror, the castle is a magnificent icon of British royalty and has been home to 39 monarchs. It is the oldest and largest occupied castle in the world, and to this day it remains the preferred residence of Her Majesty the Queen. The town of Windsor is also notable for being home to Eton College, that bastion of upper-class English boys’ education (since 1440, by the way) that has schooled a succession of British kings and prime ministers.

In the expansive grounds to the north of Windsor Castle and across the river from Eton, the Royal Windsor Horse Show has been staged annually since 1943. It began as a “Horse and Dog Show” fund-raiser for the war effort, but after a lurcher on the loose borrowed a slice of chicken from King George V’s lunch plate in ’43, dogs were barred from the show. Famous for its broad range of equine events, May’s Royal Windsor Horse Show staged classes in show jumping, dressage, driving, endurance and “showing,” which is an equine beauty pageant and a particular favourite of Queen Elizabeth II, who had over 40 horses entered into the showing classes this year. Now 96 years old and celebrating her peerless 70th year on the throne, the less-mobile Queen is reducing her public appearances, but didn’t miss watching her horses at Royal Windsor.

A staple of the UK’s landed gentry, where floral summer dresses, blazers and ties are de rigueur—Royal Windsor might be the last place you would expect to find a rider from inner-city Chicago, especially one who

started riding at the modest stables where they kept the city’s carriage horses. Yet, sipping a morning Americano in the sophisticated comfort of the Rolex hospitality suite— in pride of place by the show’s main arena, opposite the Royal box—here is Kent Farrington, a native of Lincoln Park, the son of a traveling salesman, and the former World No.1 show jumper.

“Royal Windsor is a great show,” starts Farrington, 41, in his distinctly clipped Chicago brogue, sitting beneath a framed photograph of Her Majesty presenting Farrington with the prestigious King’s Cup at Royal Windsor in 2016. “There’s big prize money, top competition and you can’t beat this setting. It’s an exciting weekend of sport.” A world away from Windsor, Farrington grew up in the shadow of Wrigley Field. His dad traded-in three second-hand laptops to buy Farrington his first horse, and heading out to Winnetka, Ill. as a teenager back in the 1990s, he scraped a few bucks together by becoming the best ponyracing jockey around. At the age of 17 he arrived at the first career crossroads: college or professional riding?

“My dad thought I was wasting my brain by pursuing sport,” admits Farrington, “particularly because the places where I was competing didn’t look anything like this where we are today. I certainly wouldn’t call it glamorous. It would have seemed to him like I was joining the circus.

“I promised that I would try my best for a few years and if I was not cutting it, then I would still be young enough that I could go back to college. But I wanted to try.” Farrington worked with two former Olympic show jumpers, Tim Grubb (GB) and Leslie Howard (USA), before Howard encouraged him to take the jump to start his own business at the age of 20.

“Leslie and I didn’t always see things the same way,” admits Farrington. “We still have a great relationship today, but after a year she said: ‘You are a talented guy but you are not a very good employee. You are strong enough in your mind and your will to succeed on your own. You have your own ideas of how you want to do things and I think you should run it on your own. Go for it.’” Giving riding lessons, training and trading horses, and competing when he could, Farrington gradually built his business, and with it evolved his own team of show jumping horses. Farrington won his first five-star show jumping grand prix at the age of 23 and today, based in Wellington, Florida—the show-jumping capital of the United States— Farrington’s stables house 65 horses. He trains elite horses and riders, runs a team of instructors and manages a team of 10 horses for his own competing. When Farrington reached World No. 1 in 2017, he had four horses that were all capable of winning five-star grands

“On Sundays we all fear Kent. He is always there or thereabouts and he is a fearless competitor”

Farrington riding Voyeur at Spruce Meadows, Calgary in 2014; at the CHIO Aachen Rolex Grand Prix in 2019 prix. It was the perfect formula and it brought Farrington his first major success, in the 2017 CHI Geneva Rolex Grand Prix, and further major success followed at the 2019 CHIO Aachen Rolex Grand Prix in Germany.

“Kent is a rider I really look up to,” confides Harry Charles, a young English rider competing at Royal Windsor. “On Sundays we all fear Kent. He is always there or thereabouts and he is a fearless competitor. Kent is a great horseman and he manages his horses fantastically to have stayed at the top level for so many years, which is something I would love to emulate.” Standing 5’ 8”, Farrington is built like a racing jockey and his horses tend to be smaller and faster than most international show jumpers. He grew up riding agile horses, and his show jumping strategy is proven.

“I prefer careful, lighter horses and usually the question is whether they will make it to jump big,” explains Farrington. “You never know until they actually go up to that level and perform. You are always going to have questions along the way. If a horse is super careful you don’t know if it will jump big enough. For a horse that jumps big, you don’t know if it is going to be careful enough or fast enough at the top level. You just don’t know until you get there.” Ranked seventh in the world at the time of writing, Farrington is nurturing a young team of horses in the hope of finding another quartet that he can steer to success at world level.

“Right now my older horses are in the twilight of their careers, while the younger ones are at their dawn,” he explains. “The baton is being passed along, but I am always looking at new horses. That is part of the game—you have to be a dreamer and a sceptic at the same time. I am a dreamer in trying to see the best in the young horses coming up, but then I have to be a realist and see when a horse is not going to be good enough.

“My horses all have the ability, but the question is whether they want to be great in our sport. It’s the same with other sports. What separates the best basketball or ice hockey player is not always that they are stronger or faster; a lot of the time the separator is the mind, desire, coupled with an understanding of the game, and that can be applied to horses; does it understand how to rise to a big occasion? Some horses are cut out for it and some aren’t. On a big stage with a big crowd and a lot of atmosphere, some horses rise to that.” The main event at Royal Windsor was the Rolex Grand Prix on the Sunday. Riding 10-year-old Orafina—a rookie to five-star show jumping in 2022—Farrington finished a creditable seventh. Patience in show jumping is a virtue, and in June at the Thunderbird Show Park in Vancouver, Farrington rode Orafina to her first five-star grand prix victory. From Wrigley Field, through Windsor Castle and Vancouver, win or lose Farrington is enjoying the ride.