Whereas many racehorses are renowned for their incredible winning careers, there’s one racehorse who is known for just the opposite. Zippy Chippy, a 1991 Thoroughbred gelding, lost an incredible 100 races during his racing career, the 100^th race being at the Northampton Fair in Northampton, Massachusetts on September 10, 2004.

Zippy Chippy’s bloodlines are impressive. The New York-bred gelding’s pedigree can be traced back to famous racers including Buckpasser, Bold Ruler, Native Dancer, War Admiral, and even La Troienne. The gelding’s owner, Felix Monserrate, traded a 1988 Ford pickup in exchange for the horse.

And though Monserrate might have had dreams that the gelding could be a potential source of winnings, Zippy Chippy had other ideas. Zippy Chippy quickly developed an affinity for refusing to leave the starting gate, biting other horses during the race, and simply pulling himself up in the middle of the race. His losing streak began to build, and tracks started to ban him because of his behavior.

As Zippy Chippy’s losing streak grew, and the number of tracks that would allow him to enter dwindled, Monserrate turned to alternative types of races. Zippy Chippy challenged baseball players to 40-yard dashes, and in 2000, outfielder Jose Herrara won the race. Zippy Chippy just managed to win by a neck in a race against harness racer Paddy’s Laddy.

Following Zippy Chippy’s career became a source of entertainment for some racing enthusiasts. People Magazine noted Zippy Chippy as one of the most interesting p.... Monserrate treated the horse as a member of his family, and though Zippy Chippy might have stood a chance at winning a claiming race, Monserrate refused to enter him for fear that the gelding might be claimed and taken away.

On September 10, 2004, Zippy Chippy entered a race at the Northampton Fair, one of the last tracks that would allow him to enter. Though his odds prior to the race were 7-2, Zippy Chippy stayed true to his habits and finished last in the race. Zippy Chippy was then retired and served as an outrider pony at Finger Lakes in Farmington, New York. During his career, Zippy Chippy raced 100 times, coming in second eight times and third twelve times. He earned $30,834.

Despite his unimpressive earnings and unusual career, Zippy Chippy retired with some of the finest racehorses to ever race in America. The Old Friends Thoroughbred Retirement Farm in Kentucky provides retirement for famous Thoroughbred racehorses, allowing the public to continue to visit with these inspiring animals after their time in the press’ spotlight has faded. An auxiliary site, Old Friends at Cabin Creek, is located just outside of Saratoga, New York, a hub for horse racing. Zippy Chippy joined Cabin Creek on April 22, 2010, and it is there that he will likely spend the rest of his life.

To learn more about Old Friends at Cabin Creek, visit their website.

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Original Source: Thoroughbred Racehorse Zippy Chippy Loses His 100th Race on Septemb...