The Maiden race is for horses that have never tasted victory. It's where they begin their journey, akin to a girl stuck in her maidenhood. Winning this race propels a horse into higher echelons of competition, gradually elevating its status. Yet, for those who repeatedly falter in the Maiden, owners often resign themselves to fate, withdrawing them from competition and redirecting their paths to other endeavours.
Yet, there are always outliers, those who defy fate's decree, blazing new trails against the current. In the annals of racing, there are a few revered as Maiden champions—horses who persist despite repeated setbacks. They embody not just sporting resilience but also the unwavering dedication of their trainers and the patience of their owners. These horses capture public sympathy, becoming symbols of perseverance. While they're often underdogs, their admirers still root for them fervently, even if victory seems elusive. It's a paradoxical admiration.
Enter Zippy Chippy, a bay stallion born into equine aristocracy on April 20, 1991. His lineage boasted icons like Northern Dancer and Buckpasser, tracing back to the illustrious broodmare La Troienne. Great things were anticipated from this scion of a prestigious line, yet somehow, success eluded him. Primitive energy coursed through him; some labelled him malevolent, others whimsical. Yet, Zippy Chippy remained resolutely himself, defiantly refusing to conform. He'd balk at the starting gate, lash out at handlers, or simply saunter off track. Eventually, many venues barred him from competition. He changed hands multiple times until his last owner, disheartened by his winless streak, contemplated the slaughterhouse.
Then came Felix Montserrat, who saw something special in the horse. In 1995, he traded his aging truck for this enigmatic creature. Zippy Chippy, in a rare display of affection, left a scar on Felix's back, a testament to their bond.
Felix deserves mention too. Arriving in the United States from Puerto Rico at 20, he harboured dreams of equestrian success. By 52, he owned five thoroughbreds, with Zippy Chippy holding a special place in his heart. He likened his attachment to familial loyalty, like parents aiding their underdog son over more successful siblings. So, he persisted, hoping against hope for a miraculous turnaround.
Zippy Chippy would gallantly approach the starting gate, only to balk and watch the race unfold, or engage in a tussle with his jockey. Yet, his demeanour always mirrored that of a champion, his spirit unyielding. Off the track, he'd playfully frolic with Felix's daughter, indulging in donuts, pizza, and beer.
For 100 races, Zippy Chippy trod a path devoid of victory—a narrative that, ironically, garners its own peculiar allure. Yet, in the spirit of fairness, it's worth noting that out of those 100 races, he clinched second place in 8 and third in 12, accumulating total earnings of $30,834 over the years. As Tom Gilcoyne, historian at the Saratoga National Museum of Racing, aptly observed, Zippy Chippy "didn't do anything to hurt the sport." It's as if his races were viewed through the lens of a telescope, distanced yet still significant.
The resilience displayed by the duo of Felix and Zippy Chippy didn't escape public notice. In 2000, People magazine featured the horse among the year's most intriguing personalities, while an entry chronicling this unconventional equine made its way into the New York Encyclopaedia.
The climax of Zippy Chippy's career arrived with his 100th and final race at the Northampton Fair in September 2004. True to form, he finished eighth out of eight participants, yet stole the thunder with a resounding ovation from the crowd, who had gathered specifically to cheer on the endearing underdog at his milestone race.
Retiring in 2010, Zippy Chippy found solace at Bobby Frankel's Thoroughbred Retirement Farm near Saratoga. Here, he found a new purpose as merchandise bearing his name—belts, hats, and T-shirts—flew off shelves, alongside mugs emblazoned with the slogan "Winners Don't Always Finish First."
Canadian humourist William Thomas took on the mantle of Zippy Chippy's official biographer, crafting "The Legend of Zippy Chippy," a book that hit shelves in 2016, chronicling the horse's quirky journey. Meanwhile, children's author Artie Bennett added a whimsical touch to the tale with his 2020 release, "The True Story of Zippy Chippy - the Little Horse Who Couldn't," catering to younger audiences with humour and charm.
Zippy Chippy's life stretched to the age of 31, and in April 2022, he bid farewell to earthly pastures, outlasting his owner Felix by seven years. Reflecting on his legacy, his biographer mused, "Zippy was proud to be a racehorse, he just wasn’t very good at it."
Yet, perhaps Zippy Chippy employed his natural talents in an unconventional manner because of his deep-seated love for his craft, unwilling to reach the finish line too soon, even if it meant taking a circuitous route.