When he was eight years old, Chicago native Kent Farrington saw an old photograph of his mother riding a horse  – a discovery that would change his life forever. That instant he decided he wanted to ride himself, not knowing that one day he would go on to become one of the best show jumpers in the world, winning prestigious tournaments around the globe and help team USA secure an Olympic silver medal at Rio 2016. But it was a long road ahead for the young rider, littered with many hurdles and obstacles along the way, before he turned professional in 1999 and his determination started to pay off…

“My very first lessons were at a carriage horse stable, where they had a riding lesson program. I went once a week for about a year,” Kent recalls. “I was really eager to to ride  –  I was a brave and aggressive kid  – and then a trainer there asked if I was interested in riding some ponies on weekends. She said that she thought I could be good at doing some racing.” Kent went on to do a couple of pony races and set his mind on becoming a jockey, but that soon changed.

“I met a steeplechase jockey who told me that it’s really going to be tough  – keeping your weight down is difficult and you end up in hospital at least a couple of times a year. I thought that it really doesn’t sound like fun, so I reevaluated doing steeplechase,” he says. “Then I saw a Spruce Meadows show jumping event on television, and that’s when I decided, okay that’s the direction I wanted to go. It was really a turning point [for me], I was probably 11 or 12…”

Kent says back then he didn’t know about the high level of interest in show jumping. “I just really liked it and wanted to see how good I could get. I was basically doing very local events, country fair-type events, but my mom was always trying to figure out how we could go to higher-level shows for me to get that kind of exposure. I kept moving up the ranks to better trainers, and many of them took me under their wing and gave me opportunities  – the industry kind of brought me up to where I am now.

“I used to watch a lot of VHS tapes, too, because growing up I didn’t have access… Every year, I would get the World Cup final videotaped and I would just play it on repeat. I’d stand in front of the TV and pretend that I was riding  – pretend that I was Nick Skelton or Rodrigo [Pessoa]…”

The tides have certainly turned for the talented rider, who is 36 now, and counts among his accomplishments winning the US Open CSIO5* twice, as well as the East Coast World Cup League, team gold at the 2011 Pan American Games, and also recording victories at the King George Cup, American Invitational, Presidents Cup, Devon Grand Prix, and Hampton Classic. He also helped team USA to victory at the inaugural Rolex Central Park Horse Show in 2014, and another notable victory came at CHI Geneva in 2015 when he won the Rolex IJRC Top 10 Final.

In 2014, another major milestone in Kent’s career followed when he became a Rolex Testimonee, joining the ranks of some of the most celebrated equestrians of our time. The Rolex family of international Testimonees extends across all ages, genders and the three Olympic disciplines of show jumping, dressage and eventing. Rodrigo Pessoa, Eric Lamaze, Meredith Michaels-Beerbaum, Scott Brash, Steve Guerdat, Kevin Staut, Jeroen Dubbeldam, Bertram Allen, Isabell Werth, Zara Tindall and Kent complete the current list of Rolex Testimonees in equestrian sports.

They are all iconic champions, chosen for the style and elegance they embody. The criteria for a Rolex Testimonee is more than simply being at the pinnacle of their sport  –  it is equally about the grace and perfection they personify. Rolex continues to be a major force behind the sport’s most prestigious athletes who represent the intelligence and accuracy of the brand through their historic sporting achievements.

The roots of Rolex and its affinity for sporting and human achievement can be traced back to the pioneering origins of the company. In 1927, after 10 hours in the water, a young English woman, Mercedes Gleitze, successfully swam the English Channel and emerged wearing a fully functioning waterproof Oyster wristwatch, invented by Rolex. She effectively became the Swiss watchmaker’s first Testimonee, marking the beginning of a long and prolific partnership between Rolex and exceptional athletes, explorers and artists, whose accomplishments bear witness to the excellence of Rolex watches and an enduring quest for perfection.

The interview with Kent takes place at his impeccable stables in Wellington, a short drive from the Palm Beach International Equestrian Centre where he will be competing in the 5* Rolex Grand Prix that evening. Over the past 10 years, Wellington has become an epicentre of equestrian sport in the USA, especially over the three-month-long Winter Equestrian Festival (WEF) that attracts many of show jumping’s elite riders seeking winter sun and unprecedented outdoor equine facilities, as the first quarter of the European show jumping circuit continues indoors.

In 2012, Rolex partnered with the Palm Beach International Equestrian Centre, further increasing the quality of competition. Through this relationship, the brand became the Official Timepiece of the WEF, which brings together some 6,000 horses and 2,000 riders from around 30 countries.

“As you can see today, the weather here is beautiful, compared to Europe where it’s really cold right now with primarily indoor riding,” Kent says. “The lifestyle here is amazing  –  we are able to train horses and compete. Rolex becoming a partner in Wellington has also helped to raise its status to a higher level.

“A lot of international riders have come [to Wellington]. I mean, there’s obviously still a great tour right now [in Europe] with indoor season and a lot of World Cup events and things like that, but there are many opportunities here to compete, too. There’s so much going on and so many different levels to jump.”

That evening, top honours for the 5* Rolex Grand Prix goes to Spain’s Sergio Alvarez Moya, and I am immediately reminded of something Kent had said earlier in the day: “This is a sport where you lose a lot more than you win, say compared to tennis. If you are one of the top tennis players in the world, you are more than likely going to make it through to one of the final rounds of a competition. In our sport, if you knock down fence number two you’re out, and it’s over. The best riders in the world probably only win 10 percent of the time, or maybe less, so there’s a lot of losing. Mentally, it takes a lot of strength  – you have to be very resilient.

“But I feel very grateful  –  this is a dream of mine to do what I’m doing. Becoming an ambassador for Rolex was also a huge moment, because that’s something much bigger than just show jumping.”

The Rolex Skydweller on his wrist  – his favourite timepiece  –  was shining in the sunlight, just like his career.