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|Last updated on July 7, 2008|
Zippy Chippy's pedigree includes many famous horses, such as Ben Brush, Buckpasser, Busanda, Bold Ruler, Count Fleet, Man o' War, Nasrullah, Native Dancer, Northern Dancer, Round Table, Tom Fool, War Admiral and the greatest "blue hen" broodmare of the twentieth century, La Troienne.
Owned and trained by Felix Monserrate and bred by Capritaur Farm, Zippy Chippy is New York bred. Tom Gilcoyne, a retired historian for the National Museum of Racing and Hall of Fame in Saratoga Springs, New York, said that Zippy Chippy "...hasn't done anything to harm the sport. But it's a little bit like looking at the recorded performances of all horse races through the wrong end of the telescope."
Felix Monserrate, who had boarded Zippy Chippy, acquired the horse in 1995 in a trade for an '88 Ford truck. Eventually, Zippy Chippy was banned from competing at numerous tracks. The only track not to ban him was at the Northampton Fair.
In August 2001, he came home first against a minor league baseball player in a 120-foot (37 m) race. (Although there are sources that say he lost this 40-yard dash, it seems there may have been two races. On August 18, 2000, Rochester outfielder José Herrera outran Zippy Chippy in a 40-yard race.) Zippy also won against a harness racer called Paddy's Laddy. He squeaked past Paddy's Laddy and his rig to win by a neck in a publicity stunt in which he spotted the trotter a twenty-length lead.
After his win, Monserrate said, "It feels good to win but it doesn't count until we do it against thoroughbreds. Who knows? Maybe winning will give him a little heart." Monserrate refused to enter his horse in a claiming race just to get a win. "I don't want any crazy people claiming him. He's like a member of my family. He's mean, he kicks, he bites, but he has a home forever with me and my daughter."
Zippy Chippy's 100th loss occurred on September 10, 2004, in the Northampton Fair at the Three County Fairgrounds. He went off at odds of 7-2, making him the second betting choice. A host of fans were there that day to cheer him at the start and to take his picture. Said his jockey, "It would be nice if people took photos at the end of the race too." However, Zippy Chippy finished last.
In December 2004, he retired to become an outrider pony at his hometown track, Finger Lakes racetrack in Farmington, New York, where he'd also been banned from racing on September 8, 1998, after failing to leave the gate with the rest of the field for the third consecutive time. As an outrider pony, he escorted horses in the post parade and led them to the gate.
In 2000, People magazine included Zippy Chippy on its list of that year's most interesting personalities. An English ad campaign used his name and image to convince kids to stay in school.
"Say you have three children", Monserrate said, "One is a lawyer, doing well. The other a doctor, very, very successful. But the third one, not so smart, so he's working at McDonald's. What do you do? Ignore him? Course not. He's the one who needs your help. That's Zippy."
Zippy Chippy's lifetime record is: 100 starts = 0-8-12, with earnings of $30,834.
Michael Blowen, founder and president of the Old Friends Thoroughbred Retirement Farm in Kentucky, made an offer of $5,000 to Felix Monserrate for Zippy Chippy to live at Old Friends at Cabin Creek: The Bobby Frankel Division of Old Friends near Saratoga Race Course in New York. "This is the first time we've offered money for a horse", Blowen said. "Believe me, $5,000 is a lot of money to us, and we can use it many other ways if Mr. Monserrate decides to back out of the deal."
Zippy Chippy arrived at Old Friends at Cabin Creek on April 22, 2010. The 19-year-old gelding joined Cabin Creek's seven other retirees and is expected to live out his life there, where he will be permanently pensioned. Cabin Creek is the first Old Friends auxiliary farm and is located just outside Saratoga, New York, in Greenfield Center; it is owned and operated by Joann and Mark Pepper.
Zippy Chippy went on tour in Kentucky in the summer of 2012 to bring attention to the safe retirement of race horses.
Other horses with long losing streaks include Dona Chepa (0 wins out of 125 starts), Ouroene (0 for 124), Glorious Spring (0 for 106, Japan), Thrust (0 for 105, North America) and Quixall Crossett (0 for 103, Britain).
- The Legend of Zippy Chippy: Life Lessons from Horse Racing's Most Lovable Loser, an official biography written by William Thomas, was published by McCelland & Stewart.
- "Zippy Chippy Pedigree". Equineline. Retrieved May 29, 2015.
- Zippy Chippy: 100 and counting, Equidaily Racing Journal
- Despite Game Effort, Zippy Chippy Gets Zip, Boston Globe
- "Zippy May Go to Old Friends" at bloodhorse.com
- "Zippy Chippy Arrives at Cabin Creek" at bloodhorse.com
- Zippy Chippy: the losingest racehorse in thoroughbred racing history
- The horse that won by losing: Zippy Chippy, racing’s famous also-ran, celebrated by Canadian author