April 5, 2016 
Grantland Rice, the great early-20th Century American sportswriter once wrote, “For when the One Great Scorer comes, To write against your name, He marks—not that you won or lost—But how you played the Game.”
Rice passed away in 1954, nearly four decades before Zippy Chippy was foaled at Capritaur Farms in Upstate New York. But this legendary racehorse has, in many ways, become Rice’s famous quote personified. His idiosyncratic story is told in William Thomas’ new biography The Legend of Zippy Chippy, due out April 5, 2016.
Born from impeccable breeding—his sire, Compliance, is a son of Northern Dancer, winner of the Kentucky Derby and the Preakness Stakes in 1964. His dam, Listen Lady, was a daughter of the stakes-winning Buckfinder, sired by 1966 Horse of the Year Buckpasser. Zippy seemed destined for greatness. Indeed, his entire pedigree is horse racing gold: Man o’ War, Count Fleet, Bold Ruler, and War Admiral were all ancestors.
But just a few steps into his young life, Zippy promptly lay down for a nap in the straw. And the rest is history.
In 100 starts, Zippy won zero. He famously refused to leave the starting gate on occasion and even lost a 40-yard sprint to a minor-league baseball player. Jose Herrera, 27, a base-stealing center fielder for the Rochester Red Wings, won the race by at least three horse lengths.
But Zippy’s tale is anything but a loser’s story. Rather early in his life, he had the good fortune of finding himself owned by Felix Monserrate, a 52-year-old trainer who traded his 1988 Ford truck for Zippy. Though the racing veteran knew better, he fell in love with Zippy, especially after the notoriously cantankerous horse proved quite willing to take orders from Monserrate’s eight-year-old daughter.
Together, Monserrate and Zippy found a way to make losing fun—and famously so. Watching Zippy rack up losses became such a popular pastime that stories about him on the Blood-Horse website got more views than stories about Kentucky Derby winners. In 2000, People Magazine voted Zippy Chippy one of the year’s “Most Intriguing Characters.”
This month, Zippy turns 25, and although his friend and trainer Monserrate passed away last year, Zippy continues to receive the care of a champion in retirement at Old Friends Thoroughbred Retirement Farm. Not at all a bad result for a world famous loser!
Catch his entire life story in The Legend of Zippy Chippy, by William Thomas, due out April 5, 2016. Hear more from the author here:
About the Author
Marjorie Wilkinson is the co-founder and co-editor of Counter-Canter Culture—a revolutionary online publication intended to unite the equestrians and equestrian-enthusiasts who aren’t afraid to kick up the dust that has settled on the conventional equine lifestyle. She is also a real-life Hollywood music supervisor and the official curator of Counter-Canter Culture’s musical column, 100% Sound.
