By Britney Grover
In March, Chester Weber won the USEF Four-in-Hand Combined Driving National Championship — for the 15th time. Having grown up on his parents’ Live Oak Plantation in Ocala, Florida, Chester nurtured an early-emerging talent and became the youngest driver to be named to the U.S. Equestrian Team at just 18. He blazed a trail as the country’s top driver by becoming the first American to win an individual silver medal in the Four-in-Hand FEI World Driving Championships, then followed it up with numerous medals and championships around the world including winning the Royal Windsor Horse Show Four-in-Hand in 2014 and 2015, earning him personal accolades from Her Majesty, Queen Elizabeth II.
In 1992, Chester started the Live Oak International as a combined driving show at his home training grounds. Show jumping was added in 2012 with the Live Oak International Grand Prix, and the 5,000-acre Live Oak has become a top equestrian destination for both drivers and jumpers. Sidelines caught up with Chester as he prepares for the 2018 World Equestrian Games to be held in Tryon, North Carolina.
What would you tell someone who was thinking about trying driving?
No time like the present to get started. Many people are afraid to try it. They say, “Oh, I’m used to sitting on a horse where I have more control.” But I encourage everybody to give it a shot. It’s a lot of fun.
What’s the best feeling you’ve ever had?
There’s a lot of euphoria associated with winning my first individual medal in 2008. That was some real validation for the work that I’d done with my life.
When traveling, is there any item you tend to forget?
Not really — we pride ourselves on having many systems in place that make sure all the trucks have lists of what goes in them, and all that gets checked really carefully. But sometimes I’ve gone to a horse show and forgotten my socks, so I had no socks for the weekend.
If you had a week off, what would you do?
I’d probably go on vacation to someplace with a beach that was warm and sunny.
What was the funniest horse moment you’ve ever had?
I’ve had many funny horse moments with my good friend Tucker Johnson. We traveled a lot together and there was always a lot of humility between us, a lot of gags and jokes and stuff.
What three food items could you not live without?
Ice cream. Probably steak, and maybe sushi
Who, equestrian or not, inspires you the most?
I think there are lots of people that have inspired me at different stages of my career about different things. I think that’s part of life, being inspired by people. I feel like I’m inspired every day by different people. Somebody who inspires me a lot and I read a lot of quotes by is Tony Robbins.
What career would you have chosen if horses weren’t an option?
The hospitality industry. I went to four years of hotel school at Cornell, and I really like the restaurant industry.
What’s your favorite country to visit?
For vacation, maybe the Maldives. I’ve only been there once, but the people were super kind and friendly, and it was beautiful. What wasn’t to like?
In three words, how would you describe yourself?
Intense, loyal and diligent
What talent do you wish you had?
I wish I could sing.
What are your hobbies?
Cooking, wakeboarding, snow skiing, tennis
What’s your favorite movie?
What’s something about you that would surprise people?
I cook for my team at the horse shows, at the end of the day, every day.
What kind of clothes do you wear?
I think you have to be appropriately dressed for different occasions, but in the gym I wear lululemon, around horses I wear Ariat, and if I’m going out I like the brand Hackett.
If someone gave you the best gift in the world, what would it be?
What type of item do you buy most often?
What’s your least favorite household chore?
Cleaning the bathroom
How would you like people to remember you?
As a horseman