Photo: Erin Gilmore
Photo: Erin Gilmore

Chester Weber

America’s most celebrated combined driving athlete relies on business jets—and four-horsepower vehicles.

Chester Weber, America’s most celebrated combined driving athlete, has garnered many awards for his international equestrian accomplishments. He has twice won a category of England’s Royal Windsor Horse Show and has taken home three World Equestrian Games silver medals and a record 15 U.S. Equestrian Federation (USEF) Four-in-Hand national championships. He has also been number one in the FEI (Federation Equestre International) world rankings.

The Ocala, Florida native is the youngest son of billionaire Charlotte Colket Weber, whose grandfather, John T. Dorrance, invented the process of condensing soup and founded the Campbell Soup Company. Raised on his family’s 5,000-acre thoroughbred breeding farm in Ocala, Live Oak Plantation, young Chester wanted to be a jockey; however, at six-foot-two and 200 pounds (jockeys typically weigh about 120), he took up driving Clydesdales instead.

Next, he tackled the top discipline of combined driving: four-in-hand, which requires handling four horses by holding all the reins in one hand. At age 18, he was the youngest driver to be named to the U.S. Equestrian Team (USET) for the World Pairs Driving Championships in the Netherlands. After advancing to the Four-in-Hand Division in 1999, he earned 12 consecutive wins.

An extraordinary equestrian event

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An extraordinary equestrian event

The FEI World Equestrian Games are expected to draw 500,000 spectators.

Weber promotes combined driving and serves on the USET board of trustees, the USEF High Performance Driving Committee, and five other equestrian committees. He has twice been named a USEF Equestrian of Honor, but he insists on sharing the spotlight with his horses, especially one named Jamaica, who has been honored as USEF Horse of the Year and inducted into the EQUUS Foundation Hall of Fame.

Weber travels frequently for competitions and pleasure, often by private jet. He lives with his wife and two young sons at Live Oak Plantation, which is where we caught up with him.

Photo: Erin Gilmore
Photo: Erin Gilmore

Can you explain four-in-hand?
If you compare it to car racing, it is the Formula 1 of carriage driving, the most intense part of carriage driving.

Can you control each horse individually?
Yes, it’s sort of like playing a piano. There’s a lot going on—adjusting reins, changing the pressure of your hands, and moving them. It’s really an art form.

Why do you think you’ve been successful?
I try to be humble and credit my horses for a lot of my success. We train horses six days a week, working on building fundamentals to come up with the best team. And like any sports franchise, we have a farm-team operation, which helps produce horses for tomorrow and other horses that aren’t in our top group, but we’re supporting them. I am a strategic thinker and a planner. I am able to make a training schedule for the horses, which includes short- and long-term fitness and performance goals, and then set them up at major events and championships to be in their best form.

So do the Clydesdales in the Budweiser ads come from your farm?
I’ve actually sold some horses to them.

Did your mother race?    
She has raised horses, but never rode racehorses.

Your father was a professor at New York Hospital-Cornell Medical Center [now Weill-Cornell Medical Center]. Did he also have a passion for horses?
Yes, when I was growing up, he was involved in the horse operation

Hard work and humility were always important when we were growing up. My parents made sure that we had a balanced childhood. We always had to work summers.

How did they teach you humility?
Horses do a great job at keeping you humble. Horses don’t know what they’re worth or what you’re worth. That’s a blessing because they judge you just for who you are and how you are to them.

When you went to college, what did you plan to do?
I studied at Cornell University’s School of Hotel Administration and made the U.S. Equestrian Team at 18. After I graduated, I went to work in the horse nutrition business and did that for several years until my equestrian pursuits took over, at which point I began to focus on that exclusively.

How do you keep in shape for competitions?
I run 10K probably once a week and run a couple of miles every day as a warmup. And I lift weights six days a week.

Is winning the result of having the fastest horses or is it all finesse?
One thing that’s interesting about four-in-hand driving is you have to get four horses to work in harmony. If I were to conduct an orchestra, I would have no idea how to conduct them so I’d make a mess of it. Now, that wouldn’t say anything about the orchestra’s ability. I am sure there are conductors who do a fantastic job getting the most out of an orchestra. It’s similar in four-in-hand driving. You’re really managing each horse, their character, their abilities, and trying to make them fit together in a harmonious way.

When you travel, do you take extra horses in case one gets sick or breaks a leg?
Right now, I work with a string of horses in my stable—about eight or nine on a daily basis—to make up that group in case there’s an injury. I take five or six with me when I’m traveling domestically.

Photo: Erin Gilmore
Photo: Erin Gilmore

What’s left for you to accomplish in the equestrian world?
I would love to be a world champion. I’ve won quite a few silver medals, but I’d like to win a gold. I work hard at it every day. We try and set goals, and we are forever trying to improve our horsemanship.

How often do you travel?
I am probably on the road 40 percent of the year.

Do you bring your family?
Yes, travel often with me. I think it will change as the boys get a little older. Maybe it’ll get a little easier.

When you fly privately, do you charter or do you have a jet share or card or a club membership?
I charter, and my family also owns some shares with NetJets and PlaneSense.

What’s your favorite business jet?
Well, it would be great to have a Gulfstream G650 because I travel to Europe often. If you are taking a short flight—when it’s one passenger on the plane—something like a Pilatus is appropriate. If I am going to New York or someplace like that, perhaps a Citation Excel would be appropriate. I think that there are different tools for different trips.

Why do you fly privately?
A private jet is the closest thing to a time machine you could have. In life, all we have really is time. Having a private aircraft just helps you be more efficient with your time. It gives me a chance to think and reflect and to catch up on work.

Not the first, but I remember riding, probably on a Learjet 31, from New York to Florida, maybe on fall break from school. It was with EJA [Executive Jet Aviation], which was a predecessor to NetJets. There was some concern, as the light hadn’t gone off for the landing gear to go down so they diverted the plane for a little bit. When we did land, I remember the plane being met by firefighters. I asked my mom if we were on the moon and she said, “Yes, we are.” That sounded like a good thing to tell a little kid to keep him calm.

When I went back to school, I recorded that experience in my journal of what I had done over vacation. My teacher called my parents into school saying, “Your son has a very good imagination. He said he went to the moon on his fall break.”

What does leadership mean to you?
I think it’s guiding—whether it’s a team of horses or an organization—to get the most out of the group of horses or the group of individuals that you are working with and really helping to bring out their individual strengths.


What’s a typical day for you?
I wake up around 5 a.m. I am in the gym by 6 and in the stable by 7:45. I am out of the stable around noon and doing office-oriented stuff in the afternoon. I usually cook dinner in the evening—I really enjoy cooking—and then I am off to bed.

Do you have any regret about your life?
No. I think we all make choices about how we want our life to be. I think if you regret things, you are going down the wrong track.

What do you want your legacy to be as an athlete?
I have always wanted to be called a horseman. And people often say, “Well, you’re clearly a wonderful horseman.” To me, horsemen and women are people in their sixties who can think exactly like a horse and understand them quite well. And I hope it’s going to be like that for me. It’s really magical to work with these majestic animals that, frankly, allow us to work with them. I mean, they are 1,200 pounds. There’s no forcing a horse to do anything.

Do you believe in horse whisperers?
Yes, I do. And I know several of them. When I have challenges with horses, I often try to reach out to people who have expertise in behavioral issues with horses. It’s not unlike if you had behavioral issues with a person. I might reach out to a psychologist or somebody like that to try to gain some insight.

Are you involved with Campbell Soup Company?
Other than being a shareholder, no. Until recently, my mom was a director. There’s a nepotism clause: if you are a director, your children can’t work there, and my mom worked there until the mandatory retirement age from the board of 73.

I am very proud of Campbell Soup, but that’s not my existence. It has afforded me some wonderful opportunities. But regardless of one’s heritage, one has to make the most of one’s life, and I feel blessed to have been able to do what I am passionate about every day.    


NAME: Chester C. Weber

BORN: June 3, 1975 (age 43), Ocala, Florida

EDUCATION: B.S., Cornell College, 1997
CAREER: Equestrian athlete who at 18 became youngest person ever to represent U.S. Equestrian Team. Fifteen-time U.S. Equestrian Federation Four-in-Hand National Champion, three-time Silver Medalist in Combined Driving at World Equestrian Games.
CHARITIES: Ocala Community Foundation,
U.S. Equestrian Team Foundation

PERSONAL:  Lives in Ocala, Florida with wife Elisabeth and sons Douglas, 4, and Hugo, 1. Enjoys cooking, skiing, waterskiing, and running.