Five Of The Worst Thoroughbreds in Horse Racing History

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A racehorse trailing far behind the pack in a race.
BetMGM @BETMGM Sep 09, 2022, 1:32 PM

An old saying in horse racing betting goes, “There’s a race for every horse.” That’s true for the majority of thoroughbreds, but not all. Some racehorses become legends because of their incredible prowess. These are the all-time champions such as Secretariat, American Pharaoh and Man O’ War. Others enter the Hall of Fame through the back door. These are the thoroughbreds that are so good at losing, so to speak, that their names have become legendary too. Online sports betting favorites they are not, but they’re part of horse racing history nonetheless. We take a look at five thoroughbreds that made the horse racing news for all the wrong reasons.

The most loveable loser in US horse racing

Zippy Chippy died in April 2022 at the age of 31. Sired by Compliance, a son of Northern Dancer and half-brother to the great El Gran Senor, he should have been a champion. Instead, Zippy Chippy became known as the worst US thoroughbred of all time. With around 100 winless starts, the bay gelding was a maiden all his life (a maiden is any thoroughbred, male or female, that’s never won a race.) His worst loss was in 2000 when he lost a 40-yard dash against an unknown horse for no reason that made sense.

Zippy Chippy’s career wasn’t completely hopeless, though. He finished second eight times and placed third 12 times, which made him $30,834 in total career earnings. Zippy Chippy wasn’t famous only for losing, though. His cantankerous personality and antics, such as stopping mid-race and digging his heels in at the gate, won him many fans. His owner-trainer, Felix Montserrate, even put him on display in carnivals. People Magazine voted Zippy Chippy one of the ‘Most Intriguing Characters’ of the year in 2000.

At the end of his career in 2004, Zippy Chippy retired to Old Friends at Cabin Creek in Greenfield Center, New York, a satellite of Kentucky’s Old Friends Thoroughbred Retirement Farm. Old Friends founder and president Michael Blowen said, “Zippy found his greatest success as a retiree. All of the volunteers at Cabin Creek adored him, and he attracted hundreds of fans to the farm each year. He was finally a star.”

The world’s most expensive loser

Back in 2006, the Green Monkey featured prominently in the horse racing news when the Coolmore stud purchased him for $16 million. That catapulted the two-year-old colt to the top of the list of the most expensive thoroughbreds of all time. Expectations were high when the Green Monkey made his debut. After all, he was a descendant of both Secretariat and Northern Dancer. But the Green Monkey didn’t rank among the top horse racing picks for long. The 2-6 betting favorite at his racing debut at Belmont Park, the Green Monkey finished third behind Roi Maudit and Sixthirteen. His standing in the NYRA bets rankings plummeted further in his second race, when he finished fourth to Giant Deputy at Belmont Park. His third and final race was a turf maiden at Hollywood Park, in which he finished fourth. Having failed to break his maiden, the Green Monkey retired on February 12, 2008, with career earnings of $10,440.

The biggest winning loser

Sometimes, an outsider defies all the odds of horse racing betting and comes out of nowhere to snatch the championship and shatter the favorite’s dreams. These are the unforgettable moments that make online sports betting so satisfying. One such stunning moment occurred at the Wolverhampton Racecourse, Midlands, UK, in February 2004. After 17 winless starts and a handicap of 16, nobody who can read horse racing odds would have put money on Quakeress. Yet she powered her way to the front of the field, gaining victory at odds of 25/1 in one of the closest finishes of all time. Quakeress went on to win one more race, then faded away after her historic victory.

Breaking the biggest losing streak

The record for the worst racehorse in Irish and British horse-racing history is currently held by seven-year-old mare Celerity. The name means ‘speed,’ but with no wins in 105 starts, Celerity seemed to be one of nature’s biggest losers instead. She had a few good moments in the past, placing second seven times, but nobody thought she would ever win a race. At the Chester racetrack in July 2021, Celerity’s live horse racing odds were as long as 200-1. Her performance seemed to bear them out, too, as she finished seventh in a field of eight. Horse racing betting can be deceiving, though. Just as a thoroughbred’s past performance is no guarantee of future success, it’s no guarantee of failure either. Celerity was only beaten by two lengths on that occasion. Not exactly one of the closest horse racing finishes of all time, but better than it seemed. Just two weeks later, on August 6, 2021, Celerity pulled off a stunning upset when Erika Parkinson rode her to victory, defeating Dandy’s Gold to snatch the $2,989 Racingtv.Com Fillies’ Handicap at Haydock. She’s still racing, with total career earnings of $25,913.57 to date.

The worst thoroughbred of all time

She was descended from giants. Dona Chepa’s sire was Stag Dinner, the foal of 1972 Kentucky Derby and Belmont Stakes Champion Riva Ridge and The Bride, full sister to Secretariat. But sometimes apples do fall far from the tree. The Puerto Rican mare got off to a bad start, finishing last in her first four races, and she showed every sign of continuing that way. Ultimately, she ran 128 races without a win, placing stone last 49 times. She placed second once in her entire career. In 2007, when Dona Chepa placed last in a six-horse field to lose her 125th race and break the previous world record, the owners of the Camarero Racetrack presented trainer Efrain Nieves with a special plaque. When Dona Chepa retired that same year, her lifetime earnings were $13,225, which works out at $103.32 per race.

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Our BetMGM editors and authors are sports experts with a wealth of knowledge of the sports industry at all levels. Their coverage includes sports news, previews and predictions, fun facts, and betting.

Our BetMGM editors and authors are sports experts with a wealth of knowledge of the sports industry at all levels. Their coverage includes sports news, previews and predictions, fun facts, and betting.