He was descended from the greatest RACEHORSES of all time, but he set the record for losing.

Zippy Chippy 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. But Zippy’s racing record was 0–100.

From his earliest days, Zippy was his own horse. 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 would go on to set his own records in his own way—by always losing.

His idiosyncratic story, told in William Thomas’ new biography The Legend of Zippy Chippy (McClelland & Stewart) is excerpted here.

At the end of Zippy Chippy’s unproductive stint at Boston’s Suffolk Downs, Charles “Bill” Frysinger unloaded his horse after eighteen winless starts, never having met him or even seen him race. By selling his once-prized possession for $2,500, he took a loss of $6,500.

Any hopes the new owner, Michael Barbarita, and his trainer, Ralph D’Alessandro, had of turning Zippy into a winner were dashed by two subpar fourth-place finishes at Finger Lakes, so they too disowned the enigmatic gelding. Zippy was being passed around like a bottle of malt liquor on skid row because his bottom line was shrinking, even if his self-esteem was not.

While his owners were feeling the pinch of expenses not covered by earnings, Zippy Chippy was not feeling their love. “I once had the misfortune of owning that dog” is how Frysinger looked back on those days. Stats men all of them, they were not a bit impressed by Zippy’s endearing personality or his comical behavior of eating the hats of passersby, or goosing backside workers from behind. Zippy once ate a pizza while it was still in the box.

By the time this New York–bred four-year-old racked up twenty losses, he had gone through two owners, three trainers, and eleven jockeys. Generally speaking, a used car will go through fewer owners and mechanics over that period of time. Many racehorses break down and are summarily retired after such an unpromising start, but Zippy seemed to take losing in stride. Indeed, he loved racing almost as much as he loved his postgame shower and meal. Even in those very early years, Zippy Chippy seemed to assume the Iron Man role. While half of the 37,000 Thoroughbreds foaled each year in North America never even get to race once, Zippy had already answered the call to post twenty times and was chomping at the bit for more.

At this point a groom and vagabond named Louis somehow acquired Zippy Chippy. It’s likely Louis bought the horse using Michael Barbarita’s name and license to do the deal or else accepted the horse on a hand-off, in which case no money was involved. The immediate savings in stabling, food, and vet bills are substantial whenever an owner rids himself of a horse not consistently finishing in the money.

Louis’ boss at Finger Lakes Racetrack was a horseman named Felix Monserrate, a fifty-two-year-old trainer with a stable of five Thoroughbreds, a few of which he owned himself. A compact, round-faced, bronze-skinned man, he had come to America from Puerto Rico as a twenty-year-old exercise boy, first galloping Thoroughbreds in South Florida, and later at Belmont Park. He was no stranger to losing; neither Felix nor Finger Lakes was considered the best in the field of racing horses. In Zippy, Felix saw a lot of himself—not too big, not running in rich circles, but a hard worker and one that didn’t quit. Zippy liked to fool around a lot; Felix liked to tour the backside with a beer. Zippy was not shaken by losing. Felix just loved the life of a horseman.

But even Felix had never before come face-to-face with a zero-for-twenty starter. It stands to reason that if you’re a Thoroughbred that runs often enough, you will eventually find yourself in a race in which the other horses are stressed, stiff, sore, in a bad mood, worried about the implications of starting a union, or pissed off about the food being served in the backside buckets. And on that day, odds are you will win. Zippy Chippy was unique in that he was destined to defy those odds. Unique? When you look up the word unique in Horse Racing for Dummies, you’ll see just an empty picture frame where Zippy failed to show up for his photo session that day.

Shortly after he took possession of Zippy Chippy and without ever having raced him, Louis decided to relocate from the snow-belt of the Finger Lakes to Florida, where the tracks have palm trees and hand-squeezed juice bars. But before he headed south, Louis had to dispose of his horse. Sadly, a horse who can’t earn enough to pay for his food is dead meat in the racing business. And there’s no such thing as a pet at a racing stable; even the dog in the barn is there to calm the horses, and the cat earns his keep by catching the mice.

When he heard his groom’s plan, the trainer went berserk. “Kill the Zippy horse!” screamed Felix. “No way, José!” This was both magnanimous of the man as well as an obvious mistake, since, as I mentioned, the groom’s name was Louis.

Louis needed $5,000 to purchase a vehicle for the trip. Felix didn’t have $5,000, but he did have an old truck. Thus, the kind of barter deal that usually involves a recently paroled brother-in-law was struck. When it comes to the term horse trading, this swap, a 1988 Ford truck for a horse who avoided the finish line like it was an electric fence, both defines the phrase and serves as its best example. The dirty white truck, which had been used to cart horses all over the country, had 188,000 miles on it. Zippy, as Felix would find out much later, ran like he had more. “That guy,” recalled Felix, “he push him around and say bad things about him, so yeah, he got the truck and I got a friend.”

From this moment on, Zippy Chippy, possibly the most stubborn and cantankerous horse ever to enter a starting gate, would be forever entwined with Felix Monserrate, the most stubborn, patient, and optimistic trainer ever to clean his boots off with a stick. With Zippy Chippy, Felix was accepting the challenge of his life, a baffling but battling no-win wonder. With Felix Monserrate, Zippy was moving from an owner to a family of horse lovers, which included the trainer’s partner, Emily Schoeneman, and their kids, Marisa and Jared. All would go on to spend the rest of their lives on horse farms and the backsides of the racetracks. It’s all they know; it’s all they love.

The most successful horsemen approach Thoroughbred racing as a business, a tough trade of buying and selling, racing the best and unloading the worst. Remaining emotionally detached from the animals is a given. By contrast, the Monserrates did not deal in racehorses; they doted on them. They cared deeply for their pure-bred racetrack brood, waiting on them hand and hoof.

“Better not love a horse” was the mantra of trainers and owners who had seen their horses sold, traded, injured, shipped off to stud farms, and euthanized on the track.

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. By way of offering his opinion of the trade, the horse immediately bit him. Just like that. Not exactly the “Felix, I think this is the beginning of a beautiful friendship” kind of moment you see in movies. But it was memorable; Felix still has the scar on his back today.

Felix figured Zippy Chippy’s problem resulted from a personality clash between the horse and his previous trainers. Zippy didn’t much care for the training sessions, which were hard and frequent. Consequently, when he got mad, which for this horse was his normal temperament, he would simply ignore the trainer.

During his perfect stretch of no wins in twenty outings, Zippy had earned the reputation of a badass racehorse, difficult to handle and impossible to motivate. Yet with those doe-like eyes and a penchant for finding trouble in the unlikeliest places, to those who knew him and worked with him, Zippy Chippy had become a lovable scamp.

Just for kicks, when he had nothing better to do, Zippy would beat the hell out of his stall and boot his water bucket around like it was a soccer ball. 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. Even the backsiders who kept a healthy distance from him admired this character of comedy begrudgingly. Although they remained alert while working with him, they had not a clue as to what he might do next. As Thoroughbreds go, Zippy had become a scoundrel of professional proportions. A life-of-the-party kind of horse, he would have looked good running a race with a lampshade on his head. In the serious business of racing horses, Zippy Chippy seemed to be honing his skills and relishing his role as the track clown.

Felix was certain he could change all that. Emily wasn’t so sure. “I mean, just look at him,” she said. “He’s a miserable, ugly-looking horse, and he’s poopy brown in color.” In fairness, the horse is quite unremarkable to look at, blotchy brown from stockings to mane, with a tail to match. Only a white marking on his forehead the size of a silver dollar gives any relief to his dark dullness.“He looks like a donkey with those big ears. He’s got a big butt and a little neck. He’s just homely.” Okay, okay, okay, Emily—so he looks more like Had the Biscuit than Seabiscuit—we get the picture. (Note: One thing you will not see at the end of this book is a footnote revealing that Emily Schoeneman eventually left the horse racing business and went into public relations.)

Emily still shakes her head at the thought that Felix would take on the role of owner and trainer of a horse that was frustrating and failing race fans everywhere, a horse that was dropping from A-list tracks to second-rate ovals faster than…well, faster than just about every horse he ever raced against. But Felix had earned the reputation of a Father Flanagan figure around Finger Lakes: a soft-hearted, humane man, a loyal friend, an absolute believer in a sport full of skeptics. “Felix always believed he could turn Zippy Chippy into a star someday,” Emily said with great wonder.

Felix, like the other owners before him, had obviously been dazzled by Zippy’s aristocratic roots. Blinded by the possibility of success this horse had inherited and oddly enamored by their new and awkward relationship, Felix was unaware that he was crossing a line trainers clearly drew in the dirt of racetracks everywhere. They bred, trained, and raced horses for money and, just maybe, fame. Period. This unwritten law was so clearly embraced by trainers it hardly needed posting. NO PETS ALLOWED!

Emily, of course, would come to love Zippy Chippy as much as Felix­—that is, as much as Felix loved the horse, and, as a matter of fact, still does. They both do. It’s complicated. But nobody loved that horse more than little Marisa, their daughter with the big eyes and a heart devoted to abandoned animals. While most little girls were getting sticky with Betty Crocker’s Easy-Bake Oven, Marisa was taking care of horses 16 hands high and 20 times her weight. “Zippy was really my horse,” she said. “They just didn’t know that yet.”

And although it would take a few more bite marks, a couple of bruises shaped like a horse hoof, and a career record full of zeros, one day Zippy Chippy would be a star. It’s hard to understand what the man saw in the horse, especially when the man was always running around the barn two strides ahead of the horse, which was quite often trying to kill him. The fact that Felix Monserrate was still alive at the end of Zippy Chippy’s career is a major victory in and of itself. But what a ride it was between the horse trade and the transformation of Zippy Chippy to a high-stakes winner in the end.

The Legend of Zippy Chippy
by William Thomas
Published 2016 by McClelland & Stewart

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