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Several billboards around Pittsfield salute Zippy Chippy, the thoroughbred gelding who rose to fame in the 1990s for racking up an impressive 100 losses. Richmond resident Roseanne Frieri is raising funds for the nonprofit farm where he retired.
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Children at Richmond Consolidated School are among the hundreds who sent Zippy birthday cards.

'Lovable Loser' Zippy Chippy Turns 30

By Brittany PolitoiBerkshires Staff
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Zippy enjoys carrot cake at his birthday party on April 17.

PITTSFIELD, Mass. — One of sports most celebrated losers turned 30 this month.

Zippy Chippy, the retired racehorse known for being winless in 100 races, observed this milestone birthday in style with a party and more than 200 cards from fans.

"He's in pretty good shape," said JoAnn Pepper, owner of Old Friends of Cabin Creek Farm in New York where the "lovable loser" has resided for about 10 years.  

"He's doing really well for 30 years old and he's quite famous, people come from all over to see him. He must have gotten over 200 birthday cards in the mail from Facebook and Twitter and all of that."

Richmond resident and sponsor of Zippy Chippy, Rosanne Frieri, facilitated (with Mary's Carrot Cake)  some billboards in Pittsfield to wish him a happy birthday and is hosting a 147th Derby Party on Saturday, May 1, to benefit Old Friends farm, located not far from Saratoga.

Born on April 20, 1991, the bay thoroughbred was later owned and trained by Felix Monserrate at Capritaur Farm in New York after Monserrate traded a 1988 Ford truck for him.

Zippy boasts the blood of champions in his veins — Man o' War, War Admiral, Native Dancer — but didn't inherit their need for speed.

His 100th loss occurred in 2004 at the Northampton Fair at the Three County Fairgrounds and, the same year, he retired from racing to become an outrider pony escorting more ambitious racers to the gate at his hometown Finger Lakes racetrack in Farmington, N.Y.
In 1998, he was banned from racing on this same track after failing to leave the gate with the rest of the field for a third consecutive time. This was not the only time Zippy Chippy had found trouble, as he was banned from numerous race tracks with the Northampton Fair — where his 100th loss occurred — as an exception.  

Despite his losses, the ironically named Zippy had an interesting career. In 2001, he broke his losing streak by beating a minor league baseball player in a 40-yard dash and, in 2000, was featured in People Magazine's list of the year's most interesting personalities.

Zippy is spending his retirement at the Greenfield Center farm, with owners JoAnn and Mark Pepper and his bonded companion, Red South Down.

His birthday party at the farm earlier this month had a wealth of attendees. It also included a horse-friendly cake and an appearance by Artie Bennett, author of "The True Story of Zippy Chippy, The Little Horse That Couldn't," who signed books at the event.

Frieri is hosting her 3rd annual Kentucky Derby Day event that will include a cocktail hour, program and race, a dinner buffet catered by KJ Nosh, and a silent auction. Tickets are $147 per person and derby attire — hats for ladies, ties for men — is encouraged.

"What's interesting about my party is when you approach the property there's going to be a 7-by-5 mural of the entrance to Churchill Downs and all the ladies and gents will be dressed up just like we're going to track," she said. "And I have a photographer coming in, he'll be taking their pictures and everybody will receive a picture upon leaving."

Frieri first became a supporter of the farm through founder Michael Blowen, who started the original location in Kentucky to care for retired race horses after learning how Derby winner Ferdinand had been slaughtered in Japan. One of Ferdinand's sons would spend his last years there. The Peppers' farm affiliated with Old Friends Equine in 2009.

"It was 2018 I decided to have a derby fundraiser at my house and I would match whatever money I made for the fundraiser, so I raised about $1,000 and then what happened was I matched the $1,000 and I flew down to Kentucky, and I met with the owner Michael Blowen, and Michael and I became instant friends," Frieri said.

"He has probably about 230 horses on the property there, and Michael's claim to fame is in 2003 he was the movie critic for the Boston Globe and decided he liked, this is how he explains it so I'm quoting him, he likes 'gambling, horses, and beer' so he decided to move his bride and himself to Nicholasville, Ky., and he opened the very first Old Friends retirement horse thoroughbred place.

"So with that being said, I did look into Friends at Cabin Creek, and I fell in love with Zippy Chippy, I mean, how can you not fall in love with a horse that had 100 races and lost every single one of them?"

She said the New York location of Old Friends, as well as the original, are "labors of love."

Frieri donated Zippy's children's book to the kids at Richmond Consolidated School, who then wrote him birthday cards for his special day. She said the book has a message that can resonate with anyone, which is to be persistent and keep your spirits up no matter whether you win or lose.

"I'm very interested in racehorses, and the fact that they need to live their life out in dignity after they've finished their racing career," Frieri added.

Zippy is so famous, she said, that fans recognized his name on her custom-printed Zippy Chippy hat in Baltimore and started chanting his name.

"We do call him the 'lovable loser,'" Pepper said. "And one of the mottos is that winners don't always finish first."

Tags: horse racing,   horses,   

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Pontoosuc Lake Being Searched for Missing New York Man

Staff Reports

The search began on Tuesday.
PITTSFIELD, Mass. — The Pittsfield Police Department is coordinating a search operation for a missing New York man on and around the southern portion of Pontoosuc Lake.
The man's identity and where in New York he was from has not been released.
A State Police truck and boat trailer was parked at the boat ramp. Several officers were in a yellow boat with equipment slowly moving through the south part of the lake on Wednesday. Several other boats were also being used.
The search commenced Tuesday morning with assistance from the Berkshire County Sheriff's Office, Environmental Police, and State Police. After searching the water for seven hours, it was determined that additional resources and equipment would be required to continue. The search resumed on Wednesday.
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