As It Happens

Zippy Chippy: the losingest racehorse in thoroughbred racing history

Hey buddy, why the long face? Zippy Chippy is a race horse who broke record after record — for being the losingest thoroughbred in North American history. We speak with the author of a new book about the horse that was more chippy than zippy.
Zippy Chippy with his owner, Felix Monserrate. (AP)

Some race horses aspire to wear a wreath of flowers. Other race horses stop to smell the flowers.

Zippy Chippy will go down in history as one of the most famous thoroughbreds in horse racing history — for never having won a single race. One hundred races without breasting the tape. Neigh, not one. Zero. Zip.

It was like Secretariat, except he was the opposite.- William Thomas

William Thomas is the author of a new book, The Legend of Zippy Chippy: Life Lessons from Horse Racing's Most Lovable Loser. He recently sat down with As it Happens host Carol Off to discuss Zippy's story.

"He should have been better than he was," explains Thomas, adding that Zippy's lineage includes famous racehorses Northern Dancer, Native Dancer and War Admiral.

As it Happens first told the story of Zippy Chippy in 1998, when he lost his 85th race. This tied him for the record for losingest horse in thoroughbred racing history.

"Losing never bothered him. He slept soundly every night. He really thought he went out there and did his best and earned a good meal," says Thomas.

"Zippy was proud every time he went to the track. His tail was up, the head was up, everything. He didn't know he was a loser. [His owner Felix] didn't know he was a loser. So they sort of stumbled along like that."

Zippy Chippy in retirement at Old Friends at Cabin Creek. (Old Friends at Cabin Creek)

Over time, the more Zippy lost, the more famous he became. He had a cult following among racing fans, who continued to bet on Zippy, still holding out hope that he might eventually win.

"The thing was, Zippy was Felix's pet, which broke every rule of horse racing. But their lives were intertwined forever and Zippy became the highlight of Felix's life," says Thomas. "It was a wonderful sort of relationship about a man and a horse, neither of which was very good a what they did, but it didn't stop them from trying."

The Legend of Zippy Chippy: Life Lessons from Horse Racing's Most Lovable Loser, is published by McCelland & Stewart.