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'He was our main character' - US racing's most popular loser dies at 31

Zippy Chippy (left) and his companion Red Down South at Old Friends Cabin Creek
Zippy Chippy (left) and his companion Red Down South at Old Friends Cabin CreekCredit: Connie Bush/Tiger Eye Photography/Old Friends

Zippy Chippy, US horseracing's most loveable loser, has died at the age of 31.

His record of exactly 100 races with no wins brings to mind British racing's hapless but popular duo Celerity, who snapped a 105-race losing streak last August, and Quixall Crossett, who failed to win in 103 starts.

The unwanted world record is held by Dona Chepa, a mare from Puerto Rico who was beaten 135 times in a row.

The son of Compliance was a retiree at Old Friends at Cabin Creek in Greenfield Center, New York, a satellite of Kentucky's Old Friends Thoroughbred Retirement Farm.

Campaigned by owner-trainer Felix Montserrate — who acquired the horse in 1995 by trading a Ford Truck — bay gelding Zippy Chippy earned fame in other ways and not just for his 100 loses, for being cantankerous and for putting on carnival exhibitions, including once racing against a baseball player.

In 2000, People Magazine voted Zippy Chippy one of the year's "Most Intriguing Characters".

Due to antics such as refusing to break from the gate and stopping mid-race, Zippy Chippy was banned from racing at some tracks, though not Northampton Fair in Massachusetts.

The gelding was finally retired from racing in 2004 and had a brief second career as an outrider's pony at Finger Lakes in New York. Although winless in his 100 starts, he did finish second eight times and third 12 times, compiling $30,834 in earnings.

Zippy Chippy, out of the Buckfinder mare Listen Lady, was bred in New York by Capritaur Farm. He sold for $2,500 at the 1995 Fasig-Tipton New York May Horses of Racing Age Sale to Michael Barbarita from the Carl Domino consignment.

In April 2010, the aging campaigner found a home at Old Friends at Cabin Creek. Under the guidance of Cabin Creek owner and manager JoAnn Pepper, Zippy Chippy finally found solace with a paddock mate, Red Down South, a chestnut New York-bred gelding.

For a period in 2012 Zippy Chippy was sent to Old Friends in Georgetown, Kentucky, in an exchange that sent Grade 1 winner Commentator to Old Friends at Cabin Creek.

"This must be the worst trade since the Red Sox sent Babe Ruth to the Yankees," Old Friends founder and president Michael Blowen quipped at the time, before noting the fan base Zippy Chippy had in Kentucky.

In recent years Zippy Chippy and Red Down South were the stars of Cabin Creek.

"Zippy was our main character here, and he lived his life his way," said Cabin Creek's Pepper. "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 found his greatest success as a retiree," added Blowen. "JoAnn and 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.

"Our thanks to JoAnn and Mark Pepper and everyone at Cabin Creek for the wonderful care they gave Zippy. I know he will be deeply missed by all."


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Published on 17 April 2022inInternational

Last updated 13:20, 17 April 2022

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