Catching Up With A Lovable Loser: Zippy Chippy

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Zippy Chippy in 2013. (Bill Littlefield/Only A Game)
Zippy Chippy in 2013. (Bill Littlefield/Only A Game)

This story was re-broadcast on September 19, 2020 as part of The Best Of Only A Game. 

Over the past 20 years, Only A Game has given many race horses their day in the sun. Bill Littlefield has waxed poetic about Cigar, sang the praises of Secretariat, remembered the actions of Affirmed, and even looked into the paranormal potential of Lisa's Booby Trap. But, one horse got more attention than he deserved…or at least more attention than he earned.

“There’s just something about that name, Zippy Chippy,” said Bill Flynn, then a reporter for OAG affiliate WXXI in Rochester, N.Y., who was on the scene in 1999 for Zippy Chippy's record setting 86th consecutive race without a win.

“Well, he jumped right out amongst the contenders and for most of the race he was there,” Flynn said. “He fell from the leaders in the last quarter-mile of the race and finished about 13 ¼ lengths back.”

That same week, Only A Game sent a reporter out to meet Zippy, which wasn't an easy feat. Once the reluctant racehorse started running, it was actually difficult to get him to stop.

As long as he wanna keep running, I’m gonna run him – even if he run slow.

Felix Monserrate, trainer

“As long as he wanna keep running, I’m gonna run him – even if he run slow,” said Zippy’s trainer Felix Monserrate. “I think he feels sad when he’s not doing something. That's why I keep training him.”

A year later, Zippy was still running. And he was still slow.

“Time now for our weekly Zippy Chippy update,” Bill Littlefield told Only A Game analyst Charlie Pierce in 2000. “Last week the little gelding, who couldn't, and never has, and no doubt never will, ran his record losing streak to 87 when he finished second at a county fair right here in Massachusetts.”

Charlie Pierce is not known for going easy on athletes, and Zippy was no exception.

“I think the phrase 'never has and likely never will' is sort of implied in the word gelding, isn't it?” Pierce said.

On the occasion of Only A Game's 20th anniversary, Bill Littlefield went in search of Zippy Chippy, to offer our apologies … and maybe a carrot.

Bill's Reunion With Zippy Chippy

Zippy Chippy runs no more. Unless he wants to – say when he's at the far end of the corral and somebody shows up at the gate with something good to eat.

That somebody is likely to be JoAnn Pepper, Zippy Chippy's landlord and his most enthusiastic fan.

“He is quite famous. He has quite a lot of fans, and actually every day he's getting new fans when they hear his story. People just think he's adorable,” Pepper said with a laugh.

Zippy Chippy's story is, of course, that he ran in 100 races without winning one. Well, actually, according to JoAnn Pepper, he ran in 97, tops.

Felix thought Zippy enjoyed losing, so he kept letting him lose.

JoAnn Pepper, Old Friends at Cabin Creek co-owner

“He stopped leaving the starting gate when it opened at Finger Lakes, three times in a row, and then you get kicked off the grounds,” Pepper explained.

“So he was kind of the Ferdinand the Bull of thoroughbred horse racing,” I offered. “He'd rather smell the flowers than participate in the competition.”

“I think so, yes,” Pepper said. “Or he just enjoyed being gracious and letting everybody else go ahead.”

Zippy Chippy did manage to finish second eight times. He got a few thirds. His career winnings totaled $30,000. It's a record that makes one wonder why his owner kept bringing Zippy Chippy to the track. JoAnn Pepper thinks part of the reason was that Zippy came cheap.

“He was owned primarily by Felix Monserrate, who got Zippy in a trade for a pick-up truck, and raced him throughout his entire career,” Pepper said.

“And how many times did he find himself thinking, ‘I should have held on to the pick-up truck?’” I asked.

“Oh, I don't know. A hundred, maybe,” she said. “I think most trainers would think, ‘I don't think this horse really wants to race,’ and Felix thought Zippy enjoyed losing, so he kept letting him lose.”

Zippy Chippy's current home is at a farm called Old Friends at Cabin Creek, established 10 years ago in Greenfield, N.Y., a quick run from the track in Saratoga Springs. Well, quick for any horse but Zippy. Anyway, Old Friends, which is supported by donations, a few grants, and fundraisers, some featuring Zippy, is home to 14 retired race horses, though capacity is supposed to be 12. According to JoAnn Pepper, Zippy Chippy is among those OK with sharing space with a pal.

“His name is Red Down South, and he's 12, and the minute they got together, they became best friends, and they have not been separated since,” Pepper said. “So he's lucky. It's really the truest horse relationship that I've ever seen. Zippy loves Red and respects him, and Red looks out for Zippy. It's beautiful.”

It was raining on the August day when I visited Old Friends at Cabin Creek. The farm was beautiful anyway. It was chilly, too, but the horses didn't seem to mind. I found myself wondering out loud in the presence of Pepper whether Zippy Chippy, reluctant race horse, laughing stock, butt of the jokes of a thousand railbirds, had at last found the perfect home.

“He has,” she said. “I think Zippy is as happy as he can be. He looks great. He's 22 years old. He's healthy. And he gets lots of carrots, so, he's well fed, and I think he's happy.”

You can visit Zippy Chippy and his more accomplished neighbors at Old Friends at Cabin Creek in Greenfield Center, NY.

This segment aired on August 24, 2013.

Headshot of Bill Littlefield

Bill Littlefield Host, Only A Game
Bill Littlefield was the host of Only A Game from 1993 until 2018.



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