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Old Friends at Cabin Creek’s Zippy Chippy Is Winning at Losing

The beloved racehorse who lost all 100 of his races celebrates the big 3-0.

Zippy once lost a 40-yard race to a minor league baseball player. (Connie Bush)

Anyone who grew up playing a sport he or she wasn’t particularly good at has heard the mantra “winning isn’t everything.” But for Zippy Chippy, a retired Thoroughbred who now resides at Greenfield Center’s Old Friends at Cabin Creek, not winning was everything.

Zippy, who was first acquired by owner and trainer Felix Monserrate in a trade for a Ford truck, is notable in the world of horse racing not for his winning career but for his impressively losing one: The dark brown gelding failed to win a single race out of the 100 he ran between 1994 and 2004. While he did scrape together a few second- and third-place finishes, Zippy was, maybe, best known for stopping in the middle of races, biting (both people and other horses) and being banned for life from Finger Lakes Gaming & Racetrack after failing to leave the starting gate three times in a row. A perennial long shot, Zippy gained quite a following: In 2000, he was named one of People’s most interesting personalities, and the same year, participated in a 40-yard race against minor league baseball player José Herrera. He lost.

These days, Zippy has become a sort of spokeshorse for Thoroughbred aftercare. In 2012, he traveled with his paddock-mate and best friend, Red Down South, to Old Friends’ Kentucky location for a fundraiser that featured Zippy-inspired merchandise (think shirts, hats and mugs) sporting the motto “Winners Don’t Always Finish First.” He also has his own children’s book, The True Story of Zippy Chippy: The Little Horse That Couldn’t and was the star of his own calendar. Additionally, he’ll be the subject of an upcoming billboard advertising campaign, per his marketing director and sponsor, Rosanne Frieri, and will be celebrating his 30th birthday, COVID willing, at Old Friends at Cabin Creek from noon-3pm on April 17. “He was the worst but never gave up,” says Frieri, a horseracing lover and aftercare proponent who refers to her monthly sponsorship of the horse as her “child support.” “I think that’s such a strong lesson,” she says. “There are a lot of people that can relate to that scenario.”

Natalie Moore

Natalie Moore is the director of content at Saratoga Living and Capital Region Living.

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