The Legend of Zippy Chippy

Life Lessons from Horse Racing's Most Lovable Loser

From acclaimed humorist William Thomas comes the funny yet poignant story of a thoroughbred racehorse that lost 100 races in a row -- but, in everyone's eyes, became the ultimate winner.

On April 20, 1991, at Capritaur Farms in Upstate New York, Zippy Chippy strolled into the world. He was born from American horse racing royalty -- Compliance (his father was Kentucky Derby-winner Northern Dancer; his great-grandfather Native Dancer, the Preakness and Belmont Stakes winner) and Listen Lady (great-granddaughter of Native Dancer). Even before his birth, the hopes (not to mention the bill for his planned production) for Zippy Chippy were high. His pedigree was horse racing gold: Northern Dancer, Man o' War, Count Fleet, Bold Ruler, War Admiral, and Buckpasser were all ancestors. His success and glory seemed inevitable.
But moments after his birth, Zippy Chippy struggled to his feet, took two steps forward . . . and stopped dead in his tracks. He looked around, took in his surroundings, maybe indulged in a little daydream, then promptly lay down for a nap in the straw. And thus began Zippy Chippy's storied racing career.
Vince Lombardi, one of the greatest NFL coaches of all time, famously said, "Winning isn't everything, it's the only thing." These words have become the battle cry of athletes, coaches, and teams everywhere, but over the years, sports have taken on a literal interpretation of Lombardi's mantra. Match-fixing, doping, sabotage, cocky and mean sportsmanship, all in the name of winning, have infiltrated and scandalized games, teams, reputations, and newspaper headlines. Yet, since his first moments in the world, Zippy Chippy ignored Lombardi and turned his nose at the concept of winning-at-all-costs. In fact, he decided to not win at all, losing, over the course of his career, 100 consecutive races, at some of the greatest tracks in the country: Belmont Park, Aqueduct, Finger Lakes, and Suffolk Downs among them. And he did so with his owner, Felix Monserrate, by his side -- a man who refused to sell Zippy, or even retire him, simply because he couldn't come in first. Soon, Zippy's cheering squad grew to include people who, enchanted by his story, would travel from all over North America to watch him lose but then happily gallop back to his stable. To them, Zippy Chippy was just like them; someone who wasn't an athlete with a million-dollar contract, or someone with movie star looks -- he was a creature who struggled, who lost, and who failed even the lowest of expectations. But, somehow, he found a way to enjoy himself and eagerly return for the next race.
Told with laugh-out-loud wit and a lot of heart, The Legend of Zippy Chippy is the story of the losing-est racehorse in North American history -- a perpetual loser who would become the winning thoroughbred in professional horse racing to steal peoples' hearts.