‘Loveable loser’ Zippy Chippy dies at 31

Saturday, April 16th, 2022

Zippy Chippys (left) and his buddy Red Down South at Old Friends at Cabin Creek. Connie Bush/Tiger Eye Photography.

Zippy Chippy, arguably one of racing’s most recognizable names during his career for his penchant for doing nothing but lose, died Saturday morning at Old Friends at Cabin Creek in Greenfield Center.

Zippy Chippy, a gelding by Compliance who made 100 losing starts in his career, lived at the satellite of Kentucky’s Old Friends Thoroughbred Retirement since April 2010. Under the guidance of Cabin Creek owner and manager JoAnn Pepper, Zippy Chippy settled into retirement and a peaceful retirement with a paddock mate, fellow New York-bred gelding Red Down South. In recent years, they 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.”

Campaigned by owner-trainer Felix Montserrate – who acquired the horse in 1995 by trading a Ford Truck – Zippy Chippy started his career on the NYRA circuit. He lost his first seven starts at Belmont Park and Aqueduct before running primarily at Finger Lakes from late 1994 to September 1998. He earned plenty of fame along the way, for his cantankerous nature and for putting on carnival exhibitions where he once raced against a baseball player.

In 2000 People Magazine even voted Zippy Chippy one of the year’s “Most Intriguing Characters.”

Banned from numerous track due to such antics as refusing to break from the gate, Zippy Chippy made 11 of his final 14 starts at Northampton in Massachusetts. He officially retired racing in 2004 and had a brief second career as an outrider’s pony at his home track, Finger Lakes. Bred by Capritaur Farm and out of the Buckfinder mare Listen Lady, Zippy Chippy finished second eight times and third 12 times, earning $30,834 over 11 seasons.

“Zippy found his greatest success as a retiree,” said Old Friends founder and President Michael 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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