This is the first in a series profiling books about horse racing. The Legend of Zippy Chippy: Life Lessons from Horse Racing's Most Lovable Loser by William Thomas explores the amazing story of Zippy Chippy who lost a record 100 consecutive races. Signed copies are available for $30 at www.williamthomas.ca.
Zippy Chippy may have been the greatest loser of all time but his story is an absolute winner.
Over the course of a 10-year racing career from 1994-2004, Zippy Chippy etched his name in history by losing a record 100 consecutive races. Zippy’s failures became famous as he captured the curiosity and the hearts of a nation with crowds of fans hoping to catch a glimpse of America’s biggest loser.
The tale of the cantankerous horse with a taste for beer and the confidence of a Kentucky Derby winner is the subject of Canadian author William Thomas’ The Legend of Zippy Chippy: Life Lessons from Horse Racing’s Most Lovable Loser.
The story of Zippy Chippy starts with Robert and Denise Kinney, a New York couple with deep pockets after finding success in New York real estate. The couple saw an ad in the Wall Street Journal for a horse farm for sale in Lynchburg, Virginia, so they bought it without much knowledge of the horse industry. After toying with the idea of converting the property into a bed and breakfast, they were talked into continuing to operate the property as a horse farm. The Kinneys even turned a nice profit on one of the first horses they bred at the farm when it sold for $50,000.
Unfortunately, the good times didn’t last long on the Virginia farm and the bills began to pile up.
“It went south in a hurry,” Thomas told Bourbon and Barns in a recent interview.
The Kinneys sold the farm in Virginia and moved to a farm in Connecticut, keeping a single mare named Listen Lady. Born in 1982, Listen Lady never won a race in four starts but she had shown some promise as a broodmare. Her first foal, a bay colt named Rambo Robert, would go on to win 22 of 93 starts and earn more than $99,000.
In 1990, the Kinneys bred Listen Lady to Compliance, an accomplished New York sire who fathered future millionaires Fourstars Allstar (winner of G1 Irish Two Thousand Guineas and more than $1.5 million) and Fourstardave (winner of 16 stakes races and more than $1.6 million).
In 1991, Listen Lady foaled a newborn colt who would be named Zippy Chippy. The lives of the Kinneys and many others would never be the same.
“Zippy was a shit- stirrer,” Thomas said. “As soon as he could run, he’d bolt by (Denise) at 100 miles per hour. He’d go to the duck pen and bang the latch with the ducks flying all over. . . He enjoyed the noise. He’d grab the bale of hay out from under the cat. And on and on and on. He just wanted to have fun.”
After three years of troublemaking on the farm, it was time for Zippy Chippy to step onto the track. With Compliance’s success at stud and Zippy’s brother Rambo Robert’s success on the track, the Kinneys had high hopes for the cantankerous colt.
“His breeding was stellar,” Thomas said. “It was royalty. . . Man o’War, Native Dancer, Northern Dancer, Bold Ruler. Almost everybody on Zippy’s chart is in the Hall of Fame. They fully expected he’d be a stakes racer.”
Then reality hit. Zippy’s racing career started on September 13, 1994 at world-famous Belmont Park on New York’s Long Island. Zippy Chippy entered the starting gates in a maiden special weight race (against other horses who had never won) and finished eighth out of nine horses. To make matters worse, Zippy was never closer than seventh and the horse who won (D’Moment) would never win again.
This started a long descent in which Zippy would lose five more races at Belmont, a few more in New York City at Aqueduct, two more in upstate New York at Finger Lakes then two more at Aqueduct. When he finished 10th of 11 horses at Aqueduct on January 8, 1995, he would be relegated to the minor leagues of horse racing for good.
While at Finger Lakes, Zippy was acquired by a groom named Louis who worked for a trainer named Felix Montserrate. Before ever having the chance to race Zippy, Louis needed to move to Florida, so he offered to sell Zippy to Montserrate for $5,000. Montserrate declined the offer but, instead, counteroffered with a 1988 Ford truck with 188,000 miles on it in exchange for Zippy Chippy. Louis accepted the offer.
Originally from Puerto Rico, Montserrate was a horse trainer with moderate success. With a stable of about 20 horses, he had a few winners but he was never close to the bigtime.
“Felix saw a lot of Zippy in himself,” Thomas said. “He was always looking for the big win. It was pretty elusive.”
Under Felix’s leadership, Zippy continued to lose. And lose. And lose. Zippy was even banned from competing at many tracks due to his failure to win a race or, sometimes, even leave the starting gate.
“Zippy liked to stop and smell the roses,” Thomas said.
As the losses mounted, Felix and Zippy developed a bond uncommon among trainers and horses.
“Felix broke the rule,” Thomas said. “Wise horsemen will tell you to never love a horse. You will have to sell them or kill them. Zippy became Felix’s pet. They loved traveling together on the road… They just loved each other in this quirky little love affair.”
Losing never bothered Zippy. In fact, Zippy never thought he lost a race.
“Zippy thought he won every race he ran,” Thomas said. “He came back with his tail high and talking to the other horses to let them know he believed he won.”
After many losing races, Felix would relax and share a beer with his buddy Zippy Chippy.
“Nutrition may have been a problem,” Thomas said.
After 87 losses, Zippy entered the Guiness Book of World Records and the famous losing horse was a part of history. USA Today featured Zippy Chippy twice and reporter Charles Karalt profile Zippy on CBS Sunday Morning. People Magazine even included Zippy in its list of the Most Intriguing Characters of the year. While wins may have eluded Zippy, fame had not.
After Zippy accumulated about 90 losses, Montserrate decided the horse (and his team) needed a win. That’s when the story of Zippy Chippy took a turn from losing horse to circus sideshow. Montserrate arranged for Zippy Chippy to race a minor league baseball player for the Rochester Red Wings. Ten thousand fans packed the stadium to watch the race in the outfield and the fans chanted down the start. 10. 9. 8. But when they got to 4, Zippy started eating the grass. Then he saw a vendor selling pretzels. When it was time to run, Zippy was so unfocused and slow to start that he gave himself no chance. He lost by three lengths. Three horse lengths, that is.
The fame didn’t change Zippy who continued to be the same old cantankerous horse as he had been back on the farm in Virginia. Chris Rancon, the ferrier at Finger Lakes, can attest to the difficulty of working with Zippy. Rancon begged Montserrate to sedate Zippy so it would be easier to work on his shoes, but Montserrate would not agree. Instead, it took four handlers to keep a hold on Zippy while Rancon worked away on Zippy’s shoes.
One day, Rancon drove up to the barn at Finger Lakes in a brand new truck. Zippy Chippy promptly walked right up to the truck and kicked it with all the might his hind legs could muster. He put dents in the shiny new truck’s front door and in the back.
“The truck was less than three hours old,” Thomas said.
Zippy continued to race and lose at Finger Lakes and a few other tracks as he approached 100 losses. Montserrate even tried to retire him a few times, but Zippy didn’t like that at all.
“He could hear the sounds of the track and he wanted to run,” Thomas said.
After Zippy’s 100th loss, he had a brief career as an exercise pony at Finger Lakes. Of course, that didn’t go well, since exercise ponies are meant to be a calming and mature force on the track next to the racehorses. Zippy’s personality was not suited for such a career and he lasted only one day.
“Zippy kept bumping the horses and bit them, because he wanted to race,” Thomas said.
Zippy was then retired to Old Friends Farm in Saratoga, NY, where he and other retired racehorses live out their lives together in peace.
“The bueaty of this story is people come to that farm to see Zippy Chippy,” Thomas said. “They have (Kentucky Derby winner) Funny Cide and ($4.5 million winner) Behrens (until he passed away in 2014). But ‘Where is the Zipster?’ They all want to see the horse that lost 100 races.”
Zippy, the loser of 100 races, has even helped the farm sell some merchandise with his image.
“He is now earning enough money to keep 22 other horses on the farm who did win races,” Thomas said.
So what is it about horse racing’s biggest loser that captures the hearts of the public?
“They see a lot of themselves in that,” Thomas said. “You and I - we’re not George Clooney. There are way, way more losers in this world than winners. The whole point of the book is we aren’t losers - we’re triers. I just love being a writer and I can’t wait to get to my desk in the morning. I don’t need an Oscar to tell me I’ve had a great career. I’m like Zippy. I try and try and never give up. I celebrate small victories.”