Zippy Chippy, 'losingest' horse, wins friends in retirement

Michael Blowen, founder and president of Old Friends in Scott County, feeds carrots to Zippy Chippy on Wednesday, July 18, 2012. The horse is on loan to the Scott County center through the month of August. Photo by Greg Kocher | Staff
Michael Blowen, founder and president of Old Friends in Scott County, feeds carrots to Zippy Chippy on Wednesday, July 18, 2012. The horse is on loan to the Scott County center through the month of August. Photo by Greg Kocher | Staff Lexington Herald-Leader

GEORGETOWN — For all of you who were the last to be picked for a team, or who were always the bridesmaid but never the bride, take heart. Your champion has arrived in Central Kentucky.

He won't feel your pain, but he will eagerly take your carrots.

Zippy Chippy, 21, the hapless horse who lost 100 consecutive races, has taken temporary residence at Old Friends, the Scott County farm for retired thoroughbreds.

So how big a loser was the horse whose bridle nameplate reads "Racing's Biggest Loser"?

Well, in 2000, he lost a 40-yard sprint to a minor-league baseball player. Jose Herrera, 27, a base-stealing center fielder for the Rochester Red Wings, won the race by at least three horse lengths.

(The loss was almost biblical in proportions. Jeremiah 12:5 reads: "If you have raced with men on foot and they have worn you out, how can you compete with horses?")

But Zippy lore doesn't end there.

Officials at Finger Lakes Race Track in Farmington, N.Y., banned Zippy on Sept. 8, 1998, after he failed to leave the gate with the rest of the field — for the third straight time.

In 2001, Zippy was last in a seven-horse field in which all the other competitors had never won, either.

On April 10, 2004, Zippy made his 100th start at the Three County Fair in Northampton, Mass. He finished dead last and was retired in 2010 to Cabin Creek in Greenfield Center, N.Y., a satellite of the Old Friends organization. Zippy finished second eight times and third 12 times, earning $30,572.

Old Friends founder and president Michael Blowen saw Zippy almost win a race in the late 1990s.

"It was at Great Barrington, Mass., and Zippy's running, and he finishes second," Blowen said. "But there's an inquiry into the horse that won."

Felix Monserrate, Zippy's owner and trainer, "starts climbing the steward's stand. 'No! No! He can't win like this!' It's the only time in the history of racing where a trainer was screaming, 'Don't put my horse up!' And he still finished second."

The Zipster did win an exhibition race against a standardbred horse named Paddy's Lady on March 17, 2001, in Freehold, N.J. The standardbred had a 20-length head start, and Zippy won by a neck. But because the race was an exhibition, he maintained his losing streak.

And Zippy is often called the "losingest horse in history," but he can't take the futility record title. Thatt belongs to Thrust, who had 105 losing starts in the 1950s.

All of this belies Zippy Chippy's pedigree. His sire, Compliance, is a son of Northern Dancer, who won the Kentucky Derby and the Preakness Stakes in 1964. His dam, Listen Lady, was a daughter of the stakes-winning Buckfinder, who was sired by Buckpasser, the 1966 horse of the year.

Monserrate acquired Zippy in a 1995 trade with his breeder for an old horse van.

In his 87th race, he came heartbreakingly close to the winner's circle: He led all the way before being edged by a nose.

In 2000, the same year he lost to the minor league player, People magazine named Zippy Chippy to its list of the year's most fascinating personalities. To his credit, the next year, Zippy did beat another minor-league player, Darnell McDonald (a former Boston Red Sox outfielder who is now an outfielder with the New York Yankees).

Monserrate sold the rights to Zippy's story to be made into a movie, but the project, like the horse, didn't come through. Blowen, a retired movie critic for The Boston Globe, said it could still "be a great movie."

Despite all this, Zippy often went off as the favorite in the pre-race odds, Blowen said.

"If you were betting the other horses, he was a dream come true because all the pools were totally skewed because everybody wanted souvenir tickets of the Zipster," Blowen said. "If he won, those $2 tickets would be valuable because that would have been his only victory."

So, in a way, it was fortuitous that Zippy never won, Blowen said.

"Then he'd be just another horse," he said. "He'd be just another bad racehorse. But he's not. Now he's something special.

"People identify with him. If there are 20 horses in a race, only one of them wins. There are 19 losers. And he just happened to do that over and over again. And most of us can identify more with losers than winners, because there are only a few of those."

Since arriving in Scott County on Friday, Zippy has not lived up to his reputation as a biting, ill-mannered cuss. He and his paddock mate, Red Down South, stick close to each other. Never one to do anything first, Zippy watched as Red took the initiative to roll in the dust.

And Zippy showed some spirit as he and Red galloped together down a hill to the paddock's edge.

"He likes running as long as it's not in a race," Blowen said.

Old Friends hopes to put together a fund-raiser using Zippy's name. There's a plan to challenge volunteers to raise pledges and then have those volunteers ride a zip line at the Mega Cavern in Louisville, a former limestone mine with 17 miles of underground passageways. The event might be called "Zip for Zippy" or some such thing.

Blowen, 65, said he doesn't plan to take to the zip line. "I'm too old and too chicken. I'm with Zippy. I'm going to let everybody else go."

In the meantime, the public can come see Zippy through August at Old Friends, where there are tours at 10 a.m. and at 1 and 3 p.m. each day.

"He's figured out what he can do really well. Nothing," Blowen said. "He looks at life and says, 'Look, that's the way it goes. It wasn't meant to be. Those guys are faster than me. They were certainly more interested in their jobs. I really didn't care about that job. I like my job now.'"