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From Rescue Horse to USEF Horse of the Year: Chester Weber’s Beloved Jamaica Turns 25

He was the international rags to riches story that won the hearts of America and the world. A Dutch-bred gelding destined for slaughter who proved too high-spirited for a job pulling a city carriage, then plucked from obscurity by one of the greatest four-in-hand drivers in history. He became a champion whose steel shoes were gifted to Prince Phillip by President Obama, and who was commemorated as a Breyer® horse model. His athleticism and driving honors earned him the title of 2008 USEF Horse of the Year, and made him a 2013 inductee into the EQUUS Foundation Horse Hall of Fame.  

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Happy 25th Birthday to Chester Weber’s Jamaica (Photo courtesy of Warmbloods Today Magazine)

We know him as the horse called Jamaica, whose 25 extraordinary years so far on this planet were recently celebrated by his loving owner, Chester Weber, at Live Oak Stud farm in Ocala, Florida. Weber, a three-time World Equestrian Games Silver medalist and 12-time U.S. National Four-in-Hand champion, is proud to have had Jamaica as his partner and companion for many years.

Jamaica’s story began in 1991 in Holland, when the partbred bay Hackney gelding, sired by British stallion Cambridge Cole (Walton Searchlight x Cambridge Madge) out of a mare with the inviting name of Welkom, was destined for slaughter. Jamaica’s fate changed when he was found by Belgian driver and FEI official Mark Wenten, who brought the gelding into a service role as a tourist carriage horse in the city of Bruges, Belgium. Jamaica’s notorious impatience for standing still to allow visitors into a carriage proved precisely the kind of get-up-and-go attitude that Wenten knew his friend Weber was seeking in a new wheel horse. Weber purchased Jamaica from Wenten in 2001.

Jamaica demonstrated aptitude for going in the wheel for the opening phase for ‘Mr. Dressage’ (as Weber has been dubbed thanks to his extraordinary success in the dressage phase), and left lead for the marathons. This placement became integral to an award-winning Team Weber, whose victory laps included seven National titles, a Silver Medal at the 2008 World FEI Championships, and the USEF National Combined Driving Single Horse Championship perpetual trophy named in Jamaica’s honor. In 2008, Jamaica was recognized with the Farnam Platform Horse of the Year award from the United States Equestrian Federation (USEF), and received one ton of Platform feed. Jamaica and Weber in turn paid-it-forward by donating the feed to two different horse rescue organizations.

In his role as an ‘equine ambassador,’ Jamaica also participated in ‘Kiss the Horse’ literacy campaigns, was featured in three books (For The Love Of The Horse, Volume III; True Horse Stories; and Beloved Horses in Second Careers), and raised funds for ReRun Thoroughbreds by painting a “Moneigh” masterpiece with his muzzle. Furthermore, when President Obama was searching for the perfect gift for Prince Phillip, he requested Jamaica’s shoes from Weber, which now hang in the Royal Stables.

In 2011, amid fans, family, and friends at the Live Oak International CAI-B, Weber retired his four-legged teammate. Now age 25, Jamaica has been basking in golden retirement at Weber’s Live Oak Stud property.


Team up with Team Weber and the horses that continue the tradition of the great Jamaica as they seek to qualify for the 2016 World Four-in-Hand Championships in Breda this summer. Follow news, live posts, video and photo galleries, and preferred product reviews at www.chesterweber.com