Zippy Chippy, horse racing's lovable loser, dies at 31

Updated Apr. 16, 2022 4:26 p.m. ET

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Zippy Chippy, horse racing's lovable loser for never winning in 100 races, has died at the age of 31.

The bay gelding was living at the Bobby Frankel Division of Old Friends Thoroughbred Farm at Cabin Creek near Saratoga Race Course in upstate New York since 2010. The farm said he died Friday night. A veterinarian had yet to determine the cause, according to the farm's Cynthia Grisolia.

Owner-trainer Felix Montserrate acquired Zippy Chippy in 1995 by trading a 1988 Ford truck for him.

The gelding's pedigree suggested he had potential to achieve success on the track, coming from a line that included such famed horses as Buckpasser, Bold Ruler, 1943 Triple Crown winner Count Fleet, Man o' War, Native Dancer, and La Troienne, one of the most influential broodmares of the 20th century.

Alas, it was not to be.

Zippy Chippy never won, but he came close. He finished second eight times and was third 12 times, with career earnings of $30,834. He competed several times at Belmont Park and Aqueduct, but mostly ran at smaller tracks. Eventually, he was banned from competing at several tracks for such antics as refusing to break from the starting gate.

He later gained greater fame for participating in stunts.

In August 2001, Zippy Chippy defeated a minor-league baseball player in a 40-yard dash. He also won against a harness horse in which he spotted the trotter a 20-length lead.

In 2000, he made People magazine's list of the year's most intriguing personalities.

Zippy Chippy’s 100th and final defeat came on Sept. 10, 2004, at Northampton Fair in Massachusetts, one of the few tracks that hadn't banned him. Sent off as the second choice in the wagering at 7-2 odds, Zippy Chippy finished last.

He retired three months later and had a brief second career as an outrider's pony guiding horses to the starting gate at Finger Lakes, his hometown track in Farmington, New York.

At Cabin Creek, Zippy Chippy shared a paddock with his pal, Red Down South, a chestnut gelding.

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

Zippy Chippy found his greatest success as a retiree, attracting hundreds of fans to the farm each year.

“He was finally a star,” said Michael Blowen, Old Friends founder and president.

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