Farewell to racing’s loveable loser: remembering Zippy Chippy, the ‘world’s worst racehorse’

Old friends: Zippy Chippy (left) and his pal Red Down South at Cabin Creek by Connie Bush/Tiger Eye Photography/Old Friends

Zippy Chippy, the hugely popular gelding who earned national celebrity for his career record of zero wins in 100 starts, died on April 15. Steve Dennis pays tribute to an equine legend – of sorts

 

A wise man once said that it wasn’t about the winning, but the taking part. That was the mantra that Zippy Chippy lived by, that his life was reckoned by, and it made him famous, made him loved, made him the subject of obituaries like this one while far better horses ended up as footnotes in someone else’s story.

Zippy Chippy: the racehorse who turned losing into an art form. Photo: Connie Bush/Tiger Eye PhotographyZippy Chippy’s life, strewn with contradictions on a personal level and on a more general plane yet all of them contributing to his myth and legend, came to its close on April 15. He was 31.

Zippy Chippy ran 100 times and never won a race. That much is fact. Then the myths crowd cloudily in. Dubbed the ‘world’s worst racehorse’, he was renowned for compiling the longest losing streak in American racing history – except he didn’t.

A horse named Thrust lost all his 105 races during the less catalogued 1950s, his ‘feat’ unheralded in an age before the internet and social media made newsworthy every insignificant iota of life.

He was feted as racing’s ‘loveable loser’ – but Zippy Chippy was an irascible animal who frequently bit his trainer Felix Monserrate and was well known for being difficult to handle, until one day Monserrate’s seven-year-old daughter Marisa wandered into his stall and began petting the old recidivist, whereupon he instantly became ‘loveable’.

Moreover, horse racing is a results-based pursuit. It’s about winning, not losing. On a wider scale, the word ‘loser’ is pejorative. No-one wants to be a loser, and losers are shunned. Yet, somehow, not Zippy Chippy.

In a world predicated upon success, Zippy Chippy turned failure into an art form. He was so bad he was great. And greatness is a currency we all recognise.

Bred to be a champion

Zippy Chippy was bred to be a champion. He was sired by Compliance, a son of Northern Dancer and a half-brother to all-time great El Gran Senor and champion Try My Best. Compliance, in his turn, sired Irish 2,000 Guineas winner Fourstars Allstar and Saratoga superstar Fourstardave, so high hopes were no doubt entertained as the three-year-old Zippy Chippy walked into the gate for his debut at Belmont Park in September 1994.

He finished eighth, beginning a trend that would eventually bring him more attention, more column inches than most Grade 1 winners. The Equibase comment for the race spoke volumes in just two words: lacked rally. Zippy Chippy would make lacking rally the cornerstone of a life well lived.

By the time Zippy Chippy reached 0-for-20, in June 1995, he had been through two trainers and was acquired by a third to save him from the slaughterhouse; even the losers get lucky sometimes. Felix Monserrate swapped a white Ford pickup truck for him, and most people reckoned he’d got the worst of the deal. Yet this was integral to the making of Zippy Chippy, if not as a racehorse but as a character, a celebrity, a legend in his own lifetime.

A backstetch Yogi Berra

Monserrate, who died in June 2015, was a small-time trainer with a talent for soundbites, a backstretch Yogi Berra whose announcements helped grease the wheels of the Zippy Chippy bandwagon. When Zippy Chippy was runner-up in two consecutive races – he did occasionally flirt with victory but never got the gal – Monserrate told the press: “My horse, he’s been losing real close lately.

As Zippy Chippy moved inexorably, entertainingly through his unending barren spell, reporters went to Monserrate for a line and were rarely disappointed. He was good copy, and good copy makes headlines, and headlines made Zippy Chippy.

“I don’t care if he doesn’t win. It’s just a lot of fun,” Monserrate once said. “Say you have three children. 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? Kick him out of the house? He’s the one you got to help the most. That’s Zippy Chippy.”

A diet of Doritos, popcorn and beer

Fifty defeats, sixty. Seventy in a row. Eighty, ninety, his appearances becoming less frequent but more eagerly awaited. And along the way, the story of Zippy Chippy acquired the sort of detail that took him out of the racing column and on to the front page, above the fold.

In September 1998 he was banned from racing at Finger Lakes in upstate New York, where he had run 70 times, because he had developed a habit of lingering in the gate as his opponents sped away. The articles included the news that Zippy Chippy liked to eat Doritos and popcorn and drink beer, making him a kindred spirit for most of those up in the grandstands cheering him to defeat after defeat.

To be fair, not every race Zippy Chippy ran ended in defeat. He had a two-for-three record against humans – including a 40-yard dash against a minor-league baseball player – and once beat a harness-racer giving him a 20-length start, all stunts designed to raise his progressively sky-high profile as that 100-race milestone drew closer.

When asked how he would feel if Zippy Chippy did one day keep his head in front, Monserrate spoke from the heart. “I would be the happiest man in the world,” he said. “You know, maybe I love him too much. I love him more because everyone puts him down.”

Old fella at Old Friends: Zippy Chippy, who lived out his days at the equine retirement facility at Cabin Creek, near Saratoga Springs. Photo: Connie Bush/Tiger Eye PhotographyBy the end, it seemed rather that everyone loved him. On September 10, 2004, the 13-year-old Zippy Chippy went to the gate for the 100th time, for a maiden race at tiny Northampton in Massachusetts.

He was 7-2 second-favourite to do something he’d never done before, bettors by now buying a ticket simply to have a souvenir of the occasion, as they had once done with Secretariat, whose record was slightly better.

Old showman didn't let us down

It would have been a disaster had he won, to come so close to sporting immortality only to give it up at the last gasp, but Zippy Chippy, who had spent his racing life letting people down, didn’t let us down. He finished last, like the old showman he had become, following the script to the end. That was it; three months later he slipped easily into retirement, possibly marking the occasion with a big bag of Doritos and a six-pack of Budweiser.

He lived through the sunset of his days at Old Friends Retirement Farm in Cabin Creek, near Saratoga, an offshoot of the well-known Thoroughbred retirement facility in Georgetown, Kentucky.

For a short period in 2012, Zippy Chippy was involved in a temporary exchange that took him to Old Friends in Kentucky while Grade 1 winner Commentator went the other way to Cabin Creek. "This must be the worst trade since the Red Sox sent Babe Ruth to the Yankees,” joked Old Friends founder Michael Blowen.

Happy New Year: Zippy Chippy and Red Down South with the team at Cabin Creek at the start of January 2022. Photo: Old Friends at Cabin Creek

Back at Cabin Creek, Zippy Chippy was the farm’s most popular visitor attraction, sharing his paddock with his pal Red Down South, winner of two more races than Zippy Chippy but not in the same league when it came to bragging rights.

“Zippy was our main character here,” said JoAnn Pepper, owner/manager at Cabin Creek. “He was so content, and wouldn’t do anything he wasn’t in the mood for. He taught me so much about life, and I’ll miss him forever.”

Weights and measures. 100 races, eight second-places, 12 times third. Prize-money of $30,834 spread across 11 campaigns. Two books written about him, innumerable articles.

Perhaps the finest recognition of his ‘talent’ came in 2000, when he made People magazine’s list of the year’s most intriguing personalities. If ever a horse could be said to have an intriguing personality, Zippy Chippy was the one.

He even had his own range of merchandise, the most popular item being a coffee mug bearing the motto ‘Winners Don’t Always Finish First’. Zippy Chippy never finished first. He was a loser a hundred times over. He lacked rally. But somehow, in defiance of all usual parameters, he made a success of life.

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