He was descended from the greatest racehorses of all time, but he was not quite born to run.
Zippy Chippy was born on April 20, 1991, in upstate New York. He was the great-great-grandson of Bold Ruler, who fathered Secretariat, and his family tree included Triple Crown Winner War Admiral, Man o’ War, Northern Dancer and Native Dancer, who alone sired 295 winning horses with a combined generated income of $183 million.
Zippy would go on to set his own records in his own way — by losing. His idiosyncratic story is told in William Thomas’ new biography “The Legend of Zippy Chippy” (McClelland & Stewart).
“Not everybody can be a winner,” Zippy’s trainer would say. “He wanna run. He’s always ready to go. But he don’t always go too good.”
From his earliest days, Zippy was his own horse. He never really took to harnesses or saddles. Told to run in one direction, Zippy went the other. He stuck his tongue out at strangers and loped while other horses galloped. He terrorized trainers yet charmed children.
Zippy’s first race, on Sept. 13, 1994, at Belmont Park on Long Island, set the tone. He was 3 years old, running at 15-1 odds against nine horses. He came in eighth.
“None of the horses that finished ahead of him had Zippy’s precious pedigree,” Thomas writes. “Disheartening was the fact that he got beat by D’Moment, a loser by 47 lengths in his first four races. Retired after only six races, D’Moment won just one race in his career — this one.”
After three more losses at Belmont, Zippy was moved to the Aqueduct Racetrack in Queens. He ran and lost four races, and in January of 1995 was demoted to the minor leagues and driven back upstate to Farmington.
There, Zippy was passed among owners and wound up in the hands of Felix Monserrate, a 52-year-old trainer who traded his 1988 Ford truck for the horse. Felix knew Zippy was a nonstarter — at 0-for-20, his losses were unprecedented for a thoroughbred. But Monserrate didn’t like the way Zippy’s previous owner treated him.
“That guy,” Felix said, “he push him around and say bad things about him. So, yeah. He got the truck and I got a friend.”
Felix, who moved to the United States from Puerto Rico at 20 to pursue his career, was unusual among trainers. “Better not to love a horse” is the motto of those who sell, trade, euthanize. Felix, like Zippy, was different: He loved.
“After waving goodbye to his groom and his van, Felix went into the barn as the new and proud owner of Zippy Chippy, a horse that had nowhere to go but up,” Thomas writes. “By way of offering his opinion of the trade, the horse immediately bit him. Just like that.”
‘Not everybody can be a winner. He wanna run. He’s always ready to go. But he don’t always go too good.’
- Felix Monserrate, trainer
Felix thought that Zippy’s performance and behavior were the result of poor training, but he underestimated the horse, who by turns was stubborn, playful and lazy.
If he didn’t feel like training, which was often, Zippy would just ignore the trainer. He’d trash his stall for fun and snatch anything a trainer or handler was holding, chew it up, then give it back. He had the most unusual diet of cupcakes, ice cream, popcorn and pizza, but his favorite snack combo was Doritos and beer, a treat he’d often share with Felix.
All the while, Felix kept entering Zippy in races, and a few second-place showings kept Felix’s hopes alive: a horse with this pedigree was bound for greatness. He just needed someone like Felix to unlock it.
“My horse, he comes second twice in a row!” Felix said.
But Zippy had a complicated relationship with racing and training, and the happier Felix got, the more Zippy loved to terrorize him.
Felix already had a scar on his back from Zippy’s inaugural bite. A few months later, Felix and Zippy were standing in front of the horse’s stall, and when Felix turned around, Zippy grabbed his shirt by the mouth and dangled the trainer in midair. As Felix flailed and yelled, his fellow track workers laughed and laughed.
Finally, Zippy put Felix down. “He’s a strong horse,” Felix said. “He can hold you for a long time.”
Other incidents weren’t as funny. There was the day Zippy cornered Felix in his stall for an hour. He held a Monserrate relative hostage for nearly four hours. Felix’s partner, Emily, called Zippy “a miserable thing who wants everything done for him when he wants it, makes faces, bites, kicks, and is not very intelligent.”
Zippy came to hate training so much that he trashed the exercise barn, kicking out part of the track’s fence and smashing the electric box. If handlers found themselves late with Zippy’s food, they’d skip delivery rather than risk his wrath. Some would only feed him with a rake.
So on the rainy November morning that Felix’s 8-year-old daughter, Marisa, went missing, his heart was in his throat. She had grown up with horses all her life, and was oddly enamored of Zippy Chippy. Felix ran to the stall.
It was deathly quiet. Felix’s view was blocked by Zippy’s rump. Below, he could only see Marisa’s little feet. No one was moving. Felix was terrified; if he spooked the horse, he could easily kill Marisa with a kick or a thrash.
And then . . . he heard laughter. Marisa was standing in front of Zippy Chippy, wagging her finger and telling him he’d been “a very bad boy,” over and over.
The horse loved it. He nuzzled her face and started gently walking around her. “And that — that was it,” Felix said. “I never seen that horse the same anymore.”
It’s not like Zippy’s demeanor changed — he could still be cranky and mean, and his job performance wasn’t getting better. But for Felix and his family, the horse was a keeper.
“He wasn’t going anywhere,” Marisa said. “My daddy would never get rid of that horse.”
Loss after loss, Felix would defend Zippy Chippy. “Say you have three children,” he’d tell local sportswriters. “One is a lawyer, doing well. The other a doctor, very, very successful. But the third one, not so smart, so he’s working at McDonald’s. What do you do, ignore him?” No, Felix would say. “That’s the one you gotta help. That’s Zippy Chippy!”
Over three years, Zippy ran 70 races at Finger Lakes, and the more he lost, the higher his star rose. But it was the race at Finger Lakes on June 23, 1998, where Zippy really set himself apart: of the six other horses bolting out of the starting gate, Zippy was not among them. The bell went off, but Zippy chose not to hear it.
This wasn’t even dwelling — the term for a horse who commits the serious infraction of breaking out of the gate slowly. This was just not running at all, leaving a very flummoxed jockey atop of a one-ton, immovable force.
As usual, Felix defended his favorite horse. “He don’t break so good,” he said. “That’s all.”
Zippy was within reach of setting his own record: just two races away from notching the most losses by an American thoroughbred.
Two weeks later, at another race at Finger Lakes, Zippy dwelt again. “Disbelievable,” Felix said. The jockey, Benny Afanador, was less diplomatic. “This horse is making me look bad,” he said. “I will never ride him again.”
Zippy was now also known as “Cellar Dweller.” He got a 60-day suspension, setting off protests in the sports pages and among fans. He was their underdog.
Felix was heartened, and offered yet another explanation for Zippy’s late starts: “He just want to see the other horses out in front of him before he run,” he said.
He spent those two months training Zippy to bolt out of he gate; one more suspension — three was the limit — and Zippy’s career would be over. It went better than Felix could have hoped: every single time, Zippy would break clear.
Zippy’s next race was Sept. 8, 1998. It was a chilly day, and the stands were packed — this race would determine Zippy’s fate. He was placed in No. 2 position, and among bettors that day, he was a favorite.
The bell went off. Zippy did not.
Eventually, his jockey got Zippy going, but it was more of a laid-back stroll.
“He had enough time to rub his itchy nose on the near pole, stop to catch his breath at the half-pole, and take a leak on the quarter pole before entering the stretch,” Thomas writes. “With number one on his silks and at number one in the program, Zippy Chippy, number one in the hearts of the faithful at trackside, had come in a disappointing last by four yards more than a football field.”
Zippy was banned from Finger Lakes for life. It won him a cover story in USA Today: “Way Out of the Running!” read the headline. Stewards who voted for the ban were publicly cutting. Bettors “were throwing their money away,” one said. “I’d look up at the board and there’d be a $20,000 bet on the horse. He was a cult figure, alright.”
“That horse is just taking up space,” another said. “You put a horse in the starting gate and he just stands there, and someone in the stands is betting the rent, well, that’s not too funny. A horse just can’t waste the public’s money like that.”
Felix was heartbroken. “I love him more because everybody puts him down,” he said.
Zippy may have been forced out of professional racing, but his fans loved him all the more for it. A New Jersey contingent presented Zippy with an enormous Hallmark card.
“The key to a true winner is that you keep on trying,” wrote one fan.
Another: “Keep trying. God knows there are millions of us who relate to your struggles.” Zippy’s professional record: 0-100.
In May 2000, People magazine named Zippy among their most interesting personalities, and when Zippy ran his next race — against a minor league baseball player named José Herrera — the national news media was there. Zippy did not disappoint, losing a 40-yard dash to the 27-year-old center fielder for the Rochester Red Wings in less than five seconds.
“I try hard, like a warrior,” Herrera said after the win. He thought it was hilarious. “I’m unbelievably fast,” he said, laughing.
Felix, typically, would not concede athletic superiority. Zippy, he said, “let José win to make him feel good.”
Today, Zippy Chippy is 25 years old and living on a retirement farm in Greenfield, NY.
Last June, Felix Monserrate died from heart problems and pneumonia. He was 72. One of his greatest wishes was to see Zippy’s life, like other legends of the track, memorialized in the movies.
Before his death, Felix told Thomas that years ago, he’d been collaborating with a screenwriter from LA. “He’s the neighbor of the guy who made the movie about the other horse,” Felix said. He meant “Seabiscuit.” “He thinks my horse is a better story.”