The horse that won by losing all the time
Zippy Chippy blew every race, but he never quit
Emily Schoeneman could see what her husband couldn’t. What she saw in Zippy Chippy, an ornery racehorse with donkey-like ears, a taste for Coors Light, pizza and Doritos, and with zero wins in 20 career races, was a colossal error in male judgment.
Felix Monserrate, Schoeneman’s spouse, saw otherwise. He was a Puerto Rican immigrant, an incurable dreamer and a horse trainer who typically lost more than he won at the Finger Lakes Racetrack in upstate New York. But his affections for Zippy Chippy were partly justifiable.
The serial loser appeared fast on paper. He had been bred for greatness, and counted Northern Dancer, Man o’ War, War Admiral and other legendary champions among his forebears.
After beginning his career amid high hopes at Belmont Park, N.Y. — home to the Belmont Stakes of Triple Crown fame — Zippy Chippy tumbled from lesser track to lesser track, until bottoming out in the horse-racing boondocks, where his owner planned to sell him to a slaughterhouse before Monserrate intervened in 1995.
He traded a beat-up white Ford pickup for the horse. For all that he lost, Zippy Chippy tried, and tried again, at least that is how Monserrate saw things. “Felix always believed he could turn Zippy Chippy into a star,” Schoeneman said recently.
And he did become a star, only not in the way Monserrate might have envisioned when he acquired him. The horse that couldn’t win, never did win a horse race, although he did beat a minor-league baseball player in the 50-yard dash.
By losing 100 times in 100 career starts, Zippy Chippy cemented his legend as a lovable loser, a rogue whose face adorns coffee mugs captioned with “Winners Don’t Always Finish First.”
People magazine listed him among its most interesting personalities in 2000. He has an entry in the Encyclopedia of New York and now he has his own book — The Legend of Zippy Chippy — written by his official biographer, Canadian humorist William Thomas.
“Felix saw a lot of Zippy in himself,” Thomas said this week in Toronto. “They were both stubborn. They both never quit, and yet Felix was proud to be a trainer and Zippy was proud to be a racehorse, he just wasn’t very good at it.”
Thomas is an avid hiker. He was tramping through the Finger Lakes region a few years back when he stopped into a bar near Zippy’s home track. The conversation turned to Secretariat, the greatest of the greats. Then, the bartender mentioned Zippy Chippy, the anti-Secretariat.
“I asked where I could find a book on Zippy Chippy” Thomas says. “But there wasn’t one.”
Now there is. It is a sports story, to be sure. But in Zippy’s life story is a deeper commentary on our win-atall-costs culture, where the temptation to cheat (see: Ben Johnson, Lance Armstrong, Maria Sharapova, Russian track and field athletes, football players, baseball players, hockey players, badminton players, etc., etc.) has hijacked the purity of competition. The 2016 Summer Olympics are coming soon. Great feats will be accomplished. But will you believe in them? Will you? What racing fans around the Finger Lakes region believed in was a horse with a big personality, who lost races in an abundance of ways, but who never quit — and didn’t cheat. In fact, on occasion, Zippy would stay in the starting gate while the other horses dashed off, ceding an insurmountable lead.
Monserrate described this tactic as Zippy wanting “to see the other horses out in front of him before he ran.”
And he always did run, eventually, prancing back to the stables afterward, head and tail held high, unbowed in defeat. As the losses multiplied from 20 to 40 to 60 to 80, the crowds at the track grew. Sportswriters appeared. Fans began asking Monserrate to sign their race programs.
“Say you have three children,” the trainer would say, explaining his loyalty to his horse. “One is a lawyer, doing well, and the other a doctor, very, very successful. But the third one is not so smart, so he’s working at McDonald’s.
“What do you do? Ignore him? He is the one you got to help the most. That’s Zippy Chippy.”
Zippy was eventually demoted from Finger Lakes to a fairground in Massachusetts. His final loss came in 2004. He broke from the starting gate, pivoted toward the grandstand and bowed to his fans, like Roy Rogers’ horse, Trigger. After stretching his winless streak (against horses) to 0-100, Zippy retired to his stall for a nap.
Now 25, he lives at a retirement farm for thoroughbreds in Greenfield Center, N.Y. During the warmer months, several hundred people a week stop by his corral to take pictures. The horses in the neighbouring paddocks were all champions.
But it is Zippy Chippy the tourists pay to see.
FELIX SAW A LOT OF ZIPPY IN HIMSELF. THEY WERE BOTH STUBBORN. THEY BOTH NEVER QUIT, AND YET FELIX WAS PROUD TO BE A TRAINER AND ZIPPY WAS PROUD TO BE A RACEHORSE, HE JUST WASN’T VERY GOOD AT IT.
— WILLIAM THOMAS, HUMORIST AND AUTHOR