Tag Archives: Zippy Chippy

Zippy Chippy, Racing’s Loveable Loser, Dead at 31

Zippy Chippy, left, and Red Down South at Cabin Creek by Connie Bush/Tiger Eye Photography.

GREENFIELD CENTER, NY – APRIL 16, 2022 – Zippy Chippy, horse racing’s most loveable loser, has died.

A retiree at Old Friends at Cabin Creek in Greenfield Center, NY, a satellite of Kentucky’s Old Friends Thoroughbred Retirement, the son of Compliance was 31.

Campaigned by owner-trainer Felix Montserrate — who acquired the horse in 1995 by trading a truck — Zippy is known more for losing races than winning them. In 100 starts, he never crossed the finish line first. But he earned fame in other ways — for being cantankerous 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 tracks due to such antics as refusing to break from the gate, Zippy finally retired from racing in 2004 and had a brief second career as an outrider’s pony at his home track, Finger Lakes in New York.

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 finally found solace with a paddock mate, Red Down South, a chestnut New York-bred gelding.

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.”

“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,” Blowen continued. “I know he will be deeply missed by all.”

For more information, please call (502) 863-1775 or visit www.oldfriendsequine.org.

Zippy Chippy Comes to Old Friends Georgetown

GEORGETOWN, KY — JULY 17, 2012 – Zippy Chippy is in the house!

Zippy Chippy, racing’s biggest loser, will be spending the summer at Old Friends, the Thoroughbred retirement center in Georgetown, KY. He is on loan from the organization’s satellite facility in Greenfield Center, N.Y.: Old Friends at Cabin Creek: The Bobby Frankel Division.

Zippy arrived in Georgetown (along with his best buddy, Red Down South) courtesy of Salle Vans on Friday July 13 and will be staying through August.  The now 21-year-old gelding is best known for losing 100 consecutive races.

The horses are part of an Old Friends exchange that sent two-time Whitney Handicap winner Commentator to New York and brought Zippy to Kentucky.

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