The Legend of Zippy Chippy

Life Lessons from Horse Racing’s Most Lovable Loser, William Thomas, McClelland & Stewart.

The Legend Of Zippy Chippy Book

“Zippy Chippy was bred to be a champion. He was procreatively designed not just to keep pace with other racehorses but to verily blow them all away coming down the homestretch.” So writes William Thomas at the beginning of “The Legend of Zippy Chippy,” which chronicles the life story of one of racing’s losingest—yet most lovable—thoroughbreds. Born April 20, 1991, at Capritaur Farm in upstate New York, Zippy Chippy is a descendant of some of the most accomplished and celebrated horses in history, including Triple Crown winners War Admiral and Native Dancer, not to mention Bold Ruler, sire of Triple Crown winner, Secretariat. Yet his pedigree never translated into results on the track. He finished his ten-year career winless in one-hundred starts, with earnings of just $30,834, a mere $308 per outing.

As Thomas notes in the book, Zippy Chippy’s adventures began at New York’s Belmont Park, site of the third leg of the Triple Crown, the Belmont Stakes. In his first race Zippy went off at 15-1 odds and finished eighth, earning zero, zilch, nada. He followed that up with third- and fourth-place finishes, and then in his fourth outing, he was ridden by jockey Jose Santos (who would one day win the Kentucky Derby aboard Funny Cide), and finished an encouraging third.

“Zippy was knocking on the door of success but not showing any real desire to come in and join the party,” quips Thomas about Zippy Chippy’s early near-successes. But things went downhill from there. In his fifth outing Zippy finished twenty-eight lengths behind the winner, and then, in a fateful race at Aqueduct on November 16, 1994, he crossed the finish line an astonishing fifty-four lengths back, a performance which, for all intents and purposes, put an end to his opportunities to run for five-figure purses.

“Zippy wasn’t much of a racetrack social climber,” offers Thomas. “He mostly followed his heart—and, okay, all of the other horses in most races—but … preferred his own individuality to trying to keep up with the Smarty Joneses,” a clever reference to Smarty Jones, who won the Kentucky Derby and Preakness Stakes in 2004.

Finger Lakes Racetrack, Home of Zippy Chippy
Those familiar with Zippy Chippy’s exploits will recall that the Zipster spent much of the remainder of his racing career at Finger Lakes Racetrack in Farmington, New York, home base of trainer Felix Monserrate, who acquired Zippy in a trade for a 1988 Ford truck with 188,000 miles on it. By the time the fifty-something Monserrate traded for Zippy, the horse had been through two owners, three trainers, and eleven jockeys on the way to twenty losses. 

Zippy didn’t appreciate Monserrate, at least not at first. “By way of offering his opinion of the trade, [Zippy] immediately bit him,” reports Thomas, a bite that left a permanent scar on the trainer’s back.

Though it was perhaps a case of unrequited love, Monserrate adored Zippy, and left no stone unturned trying to get ZC a win. “Felix tried different jockeys, shorter races, longer workouts, more days off. When that didn’t work, exercise riders were switched, saddles were changed, and routines were altered,” Thomas reveals. Nothing worked and Zippy would pile up fifty more losses before a few near-wins provided Monserrate with a glimmer of hope that his increasingly infamous horse would one day reach the winner’s circle.

Other Lovable Losers
Zippy’s tale provides the author with the opportunity to interject the stories of other “lovable losers,” like major league baseball’s Chicago Cubs (who haven’t won a World Series since 1908), as well as other racehorses with remarkably long winless streaks. Consider English horse Quixall Crossett (103 losses), Puerto Rico’s Dona Chepa (135 losses), and the USA’s Thrust (also 135 losses). Of particular note is Haru-urara, a Japanese horse that the author describes as Zippy’s doppelganger. Haru-urara went winless in over a hundred starts, which Thomas cheekily attributes to “that relentless Japanese work ethic.”

It’s probably safe to say, though, that none of the above-named horses had Zippy’s outsized personality. It’s clear from the book that ZC loved at least two things: Sweet foods (especially donuts and brown sugar & cinnamon Pop-Tarts®), and a good prank. “His favorite trick was to snatch anything from the hands and heads of handlers walking by his stall and then to return them partly chewed,” reports Thomas.

It’s also clear from reading “The Legend of Zippy Chippy” that ZC has—or at least in his younger days, had—a vicious mean streak. One longtime observer describes him as “a miserable thing who is crabby all the time, wants everything done for him when he wants it, makes faces, bites, kicks, and … is not very intelligent.” As for his meanness, Thomas relates a story in which Zippy went out of his way to kick—with both rear hooves—a brand-new Chevy truck owned by the farrier who was responsible for shoeing him, a violent “backward buck” that left two deep dents on the driver’s side of the vehicle.

Of course, racing fans rarely saw this side of Zippy and came out in droves to watch him run, however slowly. This explains why the racing stewards at Finger Lakes—who might have otherwise more readily banned Zippy, thanks to his penchant for dwelling at the starting gate—grudgingly allowed him to continue to race. “It’s not that he refuse to go,” explained Monserrate. “He just wants the other horses to go first, and he follow later,” a quote which makes Zippy sound almost polite.

Eventually Zippy did get banned at Finger Lakes, further limiting his opportunities to race to a trio of tracks that included Three County Fair in Northampton, Massachusetts. It was around this time that Failure first became aware of ZC, and in an interview for a September 2000 article titled Zippy Chippy: A Horse With No Shame, we asked Felix to explain Zippy’s lack of success. “Every time I ask him, ‘What is your problem?’, he never tells me,” said Monserrate with a laugh.

Zippy would go on to race a dozen more times after appearing in Failure, but he never tasted victory. Track officials at Northampton were sad to see him go and encouraged Monserrate to race the Zipster as long as possible. But by the fall of 2004, his trainer had the sense that it was time for ZC to retire. “We had bad luck the last couple races. Zippy, he’s tired,” explained Monserrate.

Zippy Chippy Retires to Old Friends Farm
Today, Zippy is spending his days at Old Friends Farm at Cabin Creek, “a living museum of horse racing”/home for retired thoroughbreds in Greenfield Center, New York. At Old Friends Farm he is the star attraction—an equine ambassador for promoting the humane treatment of old racehorses (who, it should be noted, are often euthanized, abandoned or slaughtered)—and generates the revenue that pays for his living expenses, as well as those of fellow residents like Driven By Success.

“A thousand people a week, and sometimes three hundred a day, come to pet him, feed him, buy his monogrammed merchandise, and pose for pictures. Zippy has earned more, much more, in retirement than he ever did racing,” notes Thomas, proving that winning isn’t the only way to finish first.

Life Lessons from Zippy Chippy
Aside from the fact that Zippy Chippy didn’t find his true calling until retirement, there are a few things that we can learn from ZC’s story—in particular, the power of persistence. “Defeat was not the outcome this horse sought, but neither was it his life’s undoing. Not to have tried time after time, that would have been his downfall,” offers Thomas, recognizing that Zippy would never have become as famous or popular as he is today had he quit racing after, say, just fifteen or twenty or seventy starts.

“Failure is not getting up to fight, again and again, in the end knowing you’ve done your absolute best, leaving the rest to fate. For that alone he can never be forgotten, and long after the remarkable races of other, more successful horses fade, Zippy Chippy will be remembered.”

Most of the other “life lessons” that are imparted in the book—covering five pages in the final chapter—are delivered with a dash of humor, in keeping with the tone of the rest of “The Legend of Zippy Chippy.”

“Never bite the hand that feeds you. Bite him in the back. That way he can still fix your supper,” is a representative example. As is, “Be the first to congratulate a rival for winning. Zippy would have done that, if he wasn’t so damn far back all the time.”

In short, “You could do a lot worse than patterning your life after the fun-loving and tenacious Zippy Chippy,” concludes Thomas. “But if you notice a guy following you around with a shovel, you’ve gone too far.”