The last quarter of 2019 proved the making of Darragh Kenny. He was the type who appeared often in the results, won a few grands prix here and there and, until recently, hovered around the good, but not best, end of the rankings (49th on the LGCT list in 2018).

All that changed last summer. At 31, the Irishman not only broke into the world’s top ten, it was win, win, win across the board – at Spruce Meadows, New York, Lexington, La Baule, Aachen, Chantilly, Paris, Brussels, London, Barcelona, and Knokke. In November’s Global Champions Tour Finals in Prague, Darragh and his top-rated partner Balou du Reventon finished second, beating two European champions and claiming €250,000 in prize money. Far more importantly, his double-clear jumping round with Balou in the Longines FEI Jumping Nations Cup Final at CSIO Barcelona was key to Ireland qualifying for the 2020 Tokyo Olympics.

His winning ways have spilled over onto the Florida circuit in 2020; in February, Darragh won the $213,300 CSI4*-W Longines FEI Jumping World Cup Wellington aboard Classic Dream and grabbed first place in the $8,000 Palm Beach Masters Warm Up with Billy Manjaro at Deeridge Farms, and rode Carthano to victory in the $37,000 Equinimity WEF Challenge Cup CSIO4* at the Winter Equestrian Festival.


DOB: January 24, 1988
Residence: Meijel, Limburg, The Netherlands
Homeland: County Offaly, Ireland
Longines World Ranking: 8th, the highest-ranked Irish show jumping athlete.
GCT Ranking: 12th, 2019 winnings €667,000
Top string:  Balou du Reventon, 13yo Oldenburg bay stallion; Classic Dream, 9yo DSP chestnut gelding; Romeo 88, 10yo ZANG bay stallion.

Life must be pretty hectic; what is a typical day like?
I spend January to April in Florida and go back and forth in the fall and summer to Tryon, Spruce Meadows, and Kentucky. I would say we average six months in America and six months in Holland. The horses that I bring over in the fall for Tryon, Washington, and Kentucky will go directly to Florida and have a break before they start up for WEF. I’ll compete the ones in Holland in Europe up until the time we go to Florida on the first of the year. I have a lot of Air Miles.

How does the operation work on both sides of the Atlantic?
About three years ago I bought our place in Meijel. I had spent a couple of summers in Holland and I really liked the area. We have 40 stables, indoor, outdoor arenas, all the necessary facilities you need to keep everything going. My business partner in America, Hardin Towell, is based in Kentucky. He has about 30 stalls there. We have four or five students working at both places and we both do a fair amount of coaching and training. In January we all come together in Wellington.

How big is your operation?
Altogether, on both sides of the Atlantic, we have about 18 staff and 60 horses. We probably sell about 20 horses a year and lease around 10. Matching people with horses is a big part of our business. I’m very lucky that in my teenage years I met a lot of people who I’ve stayed friendly with. We are all about the same age and they help me source most of the horses. They’ll go and try them for me and send me videos. I may go try them myself or just trust their judgment and buy them.

What’s the daily routine in Mejiel?
I’ll ride five or six a day at home and spend the rest of my time helping clients and giving lessons with their horses. I have a great staff who do all the office stuff. I’m lucky enough I don’t have to be in there too often.

How many generations of your family have been horse lovers?
Both my dad’s and mum’s sides of the family were involved with horses. My mum’s dad did a lot of showing in Ireland. My parents have always been in the business and so have I. I remember when I was really small my parents taking me with them to a show where they would bring seven or eight horses and be in and out of the ring, on and off the truck, so they put me on a pony and led me around all day because that was the safest place for me to be.

Can you identify a turning point in your career?
The turning point came when I was 19, living and working in Ireland. I had left school and was running my own little business out of my parents’ barn and I was doing pretty good. I had a good number of horses to ride, but I always thought maybe I should be trying to do this at a higher level. I remember sitting down with my father and him saying basically if you want to do this at a higher level, you need to go somewhere else to do it. I’m sure that was a very difficult thing for my father to say, because most of the business they were doing at that stage was through me. It would be difficult for them to have me leave, but they knew it was the right thing for me to do. My dad organized for me to go train with Missy Clark for a week. She asked me to stay on for the winter and then the following year she and John [Brennan] offered me a full-time job at North Run Farm [their training operation in Vermont and Florida].

Were sacrifices made along the way?
For sure, leaving my family behind for a long time was very hard thing to do; moving away from everything I knew. But I was really lucky when I moved to America because Missy and John were really super; they were great to me and treated me very well.

How did Oakland Ventures come about?
After I left North Run and I had been running my own business for five years, I met Hardin, who was working with Jennifer Gates at the time, and we became quite good friends. When he and Jennifer went their separate ways, he wasn’t really sure what he was doing next and I needed more help in America. About two years ago we joined together as Oakland Ventures.

Is there another ingredient besides an ultra-competitive nature that gives you an edge?
I push myself to be better every single day. Always striving to be better is the most important key to being successful in this sport; never believing you’re okay where you are. I had a period when I’d won a fair bit at North Run Farm and I said to John how great it all was, and John said to me ‘when you’re winning you have to work even harder because there’s only one direction you can go if you don’t.’ I never forgot that.

How do you view yourself?
I’m slightly on the colder side, which I think probably helps me in the ring. I don’t get very emotional about things, at least not very often. I try and keep everything very level. Every so often I will lose my cool, but for the most part I am pretty even-tempered.

Tell us something about you that that would surprise people.
There’s isn’t much surprising about me. I can’t cook ‒ that’s probably about the only thing.

If life hadn’t taken you where it has, is there another profession that would have enticed you?
I love working with numbers, so I think accounting or investment banking would have been really interesting.

Where is your favourite place in the world?
That’s a very difficult question, because I’ve been to a lot of places. I really love London. If I were to go somewhere for a week or a weekend, I would always choose London ‒ or possibly Rome.

Team Ireland (IRL) during the medal ceremony for the Longines FEI Jumping Nations Cup™ Final, Barcelona (ESP). From left to right Paul O’Shea, Peter Moloney, Team Manager Rodrigo Pessoa, Darragh Kenny and Cian O’Connor. (FEI / Linnea Rheborg/Getty Images)

Where would you most like to go that you haven’t been?
The Maldives or Bali, somewhere exotic like that. I am not a snow person; I much prefer the beach.

Where did you last go on vacation?
I went to Ibiza for a week – to the quiet side of the island.

Can you recommend a movie from the last year?
I like movies that are based on true stories; I think they are the most interesting. However, the last movie I watched was The Joker. It was kind of weird, but it was interesting to see how someone’s life could go so far wrong given particular circumstances.

What’s your guilty pleasure?
Sugary candy. I’m terrible. I eat a lot of it.

If you had a life lesson to share, what would it be?
Work hard and be patient and persistent and things will work out for you in the end.

If a genie were to give you three wishes, what would you wish for?
My wishes have certainly changed as I’ve grown older. As a kid you don’t know what’s really important. So number one, I would wish for my family to be healthy for a long time; number two, for me to have good horses for the rest of my career; and three, I would love to be able to sing, because I’m really terrible!

If you were having a dinner party and could invite anyone, living or dead, who would you invite?
Roger Federer and Tiger Woods, two incredible sportsmen.

If you cast away on a desert island and could take a book, a recording, and one luxury item, what would you take?
I’d leave out the book and the record if I could take a life-time’s supply of Brunello di Montalcino! I love Italian red wine.

Money or medals, what’s more important to you?
Definitely medals, because you can keep them forever.

Do you have a burning ambition?
I would love to be number one in the world and I would love to win an Olympic gold medal, either individual or team – preferably both.

What’s on the horizon for you?
World Cup Finals if I qualify, and obviously Tokyo, that’s the main goal for next year. Luckily, I have three super, super horses to aim for Tokyo with.