Zippy Chippy – The Worst Racehorse of All Time (Aka. The Horse That Never Won a Race)

If a horse is to etch their name into racing folklore, they will almost always need to perform feats of equine excellence. Think Frankel and his destruction of all rivals across a perfect 14-race career, or, over jumps, Red Rum achieving the seemingly impossible by landing the Grand National not once, not twice, but three times. The Sir Henry Cecil and Ginger McCain icons earned their legendary status through a combination of talent and willingness to give their all at the track.

However, there is an alternative, probably far easier route to racing immortality, perhaps best illustrated by a lovable rogue going by the name of Zippy Chippy. Here we have a thoroughbred distinctly short in the essential areas of ability and effort, and yet one who achieved a cult-like following, inspired two books and a range of merchandise, and was met with an outpouring of tributes upon his death in 2022 at the grand old age of 31.

So, what did good old Zippy do to achieve such status? The answer to that question lies in the gelding’s consistency – namely, a consistent ability to lose. From stone-cold last to runner-up, Zippy Chippy filled all finishing positions over the course of his career – all bar that all-important first place. Despite an impeccable pedigree and seemingly easy opportunities in an endless stream of maiden contests, the bonkers bay could not be persuaded to put his head in front, retiring with an unblemished record of 100 defeats from 100 races.

It All Looked So Good on Paper

Quite why Zippy Chippy proved so incapable at the track remains a mystery to pedigree fans, with the colt’s breeding page featuring the likes of Triple Crown winners Count Fleet and War Admiral, US Racehorses of the Year Man o’ War and Tom Fool, and one of the most influential sires of all time, Northern Dancer. Anyone assessing the trends of the family may have expected Zippy Chippy to progress to be a Graded race contender. However, trends are there to be broken, and Zippy Chippy didn’t mess around on his spectacular descent to infamy.

Starting as he would mean to go on, Zippy Chippy contrived to lose his first 20 races, testing the patience of connections and calling his career as a racehorse into question. However, Felix Monserrate must have seen something he liked in our hapless hero, and in 1995, he persuaded the owners to take his White Ford Truck in exchange for the horse.

New Owner – Same Old Zippy

Not only owning the horse, Monserrate also took it upon himself to train Zippy Chippy. Perhaps a change of scenery would spark the reluctant racer into life? Not a bit of it. 20 losses became 30, 30 became 40, 40 became 50, and the legend began to grow. Seemingly enjoying a diet of Doritos, popcorn, and beer, Zippy Chippy at least had a lot in common with many amongst his increasing fanbase – although oats, water, and standard horse feed may have been more conducive to a higher standard of racecourse performance.

From his base at Capritaur Farm in New York, Zippy Chippy took his terrible tour to Aqueduct, Belmont Park, Finger Lakes, Northampton, Penn National, Suffolk Downs, and Thistledown – gracing each and every track with his impressive and varied ways of losing a horserace. Simply running much slower than everything else was his staple offering, but he did occasionally mix things up by refusing to leave the starting stalls at all or stopping midrace – possibly when catching the whiff of a potential victory.

Not Always a Loser

Whilst he never did manage to win an official race at the track, the horse at least finished second on eight occasions – coming closest to ruining his record when going down by just a head at Northampton on the 1st of September 2000.

Zippy Chippy Results and Winnings
Zippy Chippy Results and Winnings, via Equibase

With the standard route to a win conclusively proving to be a dead end, a little imagination would be required to get Zippy Chippy into the winner’s enclosure. But get there he did, beating two baseball players in a 40-yard dash in the early 2000s (although losing to the particularly speedy outfielder José Hererra in another horse vs human sprint), and, most impressively, giving a 20-length start and a beating to an actual horse – albeit one which was pulling a cart.

Declared on 100

Zippy Chippy’s final start came at Northampton on the 10th September 2004, with the fans flocking to the track to see if the apple of Felix Monserrate’s eye could make it to 100 defeats. Against all reason, Zippy Chippy was sent off as the 7/2 second favourite that day but rewarded his fans in style – finishing last of the 8 runners, beaten 11 lengths.

Having achieved the century, Zippy Chippy was promptly retired and enjoyed a short career ponying runners to the start at Finger Lakes, before heading off into the sunset to take up residence at the Old Friends Thoroughbred Retirement Farm near Saratoga Racecourse.

Having finally found the pace of life he had long been striving for, Zippy Chippy proved to be a natural at the retirement game. Befriending the relatively prolific Red Down South – who won twice during his long career – Zippy became something of a tourist attraction, showing no signs of his previous habits of biting anyone in the vicinity or lifting those who strayed too close by the collar. Embarking on a tour in 2012, Zippy raised a significant amount of money for retired racehorses before living out his final days in comfort with his new-found friend.

Not the Worst of All Time

Whenever Zippy is remembered in the news, he is regularly labelled as “the worst racehorse of all time”. That isn’t quite fair on our recently departed star. Bad he might have been, but not so bad as the following cast of racecourse flops: Quixall Crosset (zero wins from 103 starts), Haru Urara (0 from 113), Costano Mille (0 from 123), Ouroene (0 from 124) and Dona Chepa (0 from 135). Zippy did also amass $30,834 in prize money over the course of his career – which may at least have covered the cost of that Ford Truck which brought him to the Monseratte yard in the first place!

Remembered in Literature

The Legend of Zippy ChippyThe impressive feats of Zippy have proved sufficient to inspire the penning of two books, going by the titles of “The Legend of Zippy Chippy: Life Lessons from Horse Racing’s Most Lovable Loser”, and “The True Story of Zippy Chippy: The Little Horse That Couldn’t”. Accurate as those titles may be, this enigmatic equine – who made the People Magazine list of most interesting personalities in 2000 – is perhaps best remembered by the slogan emblazoned on the official Zippy Chippy mug, “Winners Don’t Always Finish First”.