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Chester Weber

Chester Weber Bio

A Winner is – Chester Weber, the United States’ most celebrated Combined Driver and the nine-time USEF Four-In-Hand National Champion, is not only a gifted driver but also a driver who consistently takes the sport of Combined Driving to the next level. Chester became the first American to ever win an individual medal at the World Driving Championships in 2008 when he won the Individual Silver Medal in the Four-in-Hand World Driving Championships in Beesd, The Netherlands. He topped his own record again winning the Individual Silver Medal and the Team Bronze Medal at the 2012 Four-in- Hand Driving World Championships at Reisenbeck, Germany.  During his 2012 European tour, Chester was dubbed “ Mr. Dressage” as he dominated the dressage phase at CAI Lahden, CAI Beekbergen and won the dressage at CAIO Aachen with a record-breaking score of 33.54.  He remains undefeated in 2013 on US soil as he once again heads to Europe to take on the best of the best in the world.


A True Team Player- Chester took the sport of Combined Driving to an entirely new level during the 2010 World Equestrian Games in Lexington, Kentucky in October when he proved that he is a world-class competitor whose greatest desire is to see American driving succeed. On the first day of the Combined Driving competition, a standout dressage test had Chester tied for second place with Ijsbrand Chardon of The Netherlands. During the marathon, things turned disastrous for Chester when one of his horses put a leg over a trace and a groom had to dismount to help the horse, which added points to Chester’s score and put him out of the running for an individual medal.


Losing the ability to win an individual medal was a blow to the goal-oriented and driven driver, but always the consummate competitor he put aside his disappointment and attacked the cones phase with a vengeance in hopes that his score would propel the U.S. team onto the medal podium. Always graceful under pressure, Chester’s cones phase proved to be the silver lining of the weekend as his award-winning score pushed the U.S. team into second and helped them take home the Silver Medal.


Paying It Forward Is A Way of Life- While Chester’s ability to dominate the competitive field has built a large fan base for the driver, it is his heart and generous spirit that his fans speak about most. In April of 2011, Chester heard about a fund raising event for the local Humane Society in his hometown of Ocala, Florida, and he offered to give his winning Silver Medal from the World Equestrian Games to the event, saying it would be better to auction the ribbon off and raise money than to have it hanging in his tack room. The ribbon became part of an online auction and was purchased by an anonymous bidder. The new owner of the ribbon said he had experienced Chester’s overwhelming generosity at a show earlier in the year and purchased the ribbon out of respect for Chester’s exceptional horsemanship and sportsmanship. The anonymous auction ribbon winner then returned the ribbon to Chester and thanked the driver for showing not only drivers, but human beings everywhere, how life should be lived.


As an all-around sportsman and a talented competitor at the top of his sport, Chester continues to be an avid promoter of Combined Driving. Despite a rigorous training schedule and a steady competitive schedule, Chester is a tireless showman and participates in driving exhibitions across the nation to promote Combined Driving, a sport he calls his “true passion.” Chester also willingly offers free clinics and carriage rides to countless charities for fundraising purposes, always stepping up to offer his services to support worthy causes.


A Driving Force in Horse Sport- Chester is not only committed to promoting Combined Driving, but is an avid supporter of all equestrian sports and he serves on the United States Equestrian Team Foundation (USET) Board of Trustees. Chester also serves on the United States Equestrian Federation (USEF) High Performance Driving Committee, the National Driving Committee, the Safety Committee, the Hearing Committee, the Licensed Officials Committee and the Driving Technical Committee. Chester is also the chairman of the Active Athlete’s Committee and served on the Dressage Search Committee. In addition, Chester serves on the advisory board of the prestigious Equestrian Quarterly magazine.


Inspiring a Nation- Chester has twice been named as a USEF Equestrian of Honor, but he always shares the limelight with his horses, most famously his horse, Jamaica, who was named the 2008 USEF Horse of the Year and in 2013 was inducted into the EQUUS Foundation Hall of Fame. Jamaica’s fame from slaughterhouse horse to Silver Medalist caught the attention on the nation’s equestrian community.  A Breyer horse was created in his likeness and was debuted at the 2010 World Equestrian Games and Jamaica’s shoes, a presidential gift from president Obama hang in the Royal Stables in England.


Athlete Bio

Hometown: Ocala, Florida

Number of years riding: Driving Horses for 27 years

Career accomplishments to date:

  • Individual Silver Medal FEI World Driving Championships 2008 and 2012
  • Team Silver Medal USA at WEG 2002, 2011
  • Team Bronze medal 2012 World Championships
  • 9 time USEF National four in Hand Champion
  • 2 time USEF National pair champion

How you got started in your event: Too big to be a jockey at just under 200 lbs and 6 foot 2 inches

Length of time you’ve been sponsored by Ariat:  Since 2010

Favorite Ariat product (by name):  Navy down filled vest

Proudest career moment: Winning my 1st individual medal at the FEI World Championships in 2008

Tell us about your first horse: Crumpy, was a pony that I began riding with my sisters and brothers, he was one of the best teachers to date

You ride because:  it is my passion

If you weren’t a professional rider, you would be a: Chef

Favorite mentor or idol growing up: In the driving sport? Michael Freund

Favorite place to travel: Maldives, I have only been there once but I don’t sit still well and there I could be calm in my body and mind

Name one fun fact that people don’t know about you: I worked in 1996 for a restaurant company as a line cook

Favorite way to unwind outside of the barn: Cooking, Tennis, Snow or water skiing

Good luck charm: Changes all the time, I am not really supersticious