The horse that lost 100 races, but won a family’s heart

By Maureen Callahan as published in the New York Post

Life Lessons from Racing’s Most Lovable Loser

He was descended from the greatest racehorses of all time, but he was not quite born to run.

Now-retired Zippy Chippy descended from champions -- but finished with a professional record of 0 for 100. Photo: Courtesy of Emily Schoeneman
Now-retired Zippy Chippy descended from champions — but finished with a professional record of 0 for 100. Photo: Courtesy of Emily Schoeneman

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.”

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.”…(CONTINUED)


  1. Zippy sure must be one of the very few “losers” to not be sent “down the road”! He’s a lucky horse. Apparently stayed sound even after all those races.


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