Zippy Chippy

The nine-year-old brown gelding owns a remarkable losing streak.

“Zippy's been bad. He's in the barn,” says Carrie, 12-year-old niece of Felix Monserrate, owner and trainer of Zippy Chippy, one of the losingest thoroughbreds in U.S. history. The nine-year-old brown gelding with an attitude has a remarkable track record, having run 88 races without a single victory. The issue isn't necessarily Zippy's speed; he was parented by Compliance and Listen Lady (and is a blood relative of Northern Dancer, who won the 1964 Kentucky Derby). Rather, Zippy's problem is mostly between the ears.

Over his 88 starts Zippy has had seven second-place finishes and 12 third-place efforts. Much to the chagrin of handicappers, trouble seems to follow Zippy around the track. He has been known to break at the start, pull up mid-race, and has even tried to bite other horses at the finish line. His propensity for flat-out refusing to leave the gate has led to him being banned from running at Finger Lakes—his hometown track in Farmington, New York—and just about everywhere else. “Every time I ask him, 'What is your problem?’, he never tells me,” chuckles Monserrate. 

On September 1, Zippy had a near-brush with victory, finishing second, by a neck, to Black Rifle in a five-furlong race at the Three-County Fair in Northampton, Massachusetts. While the competition wasn't the strongest (none of the other entrants had ever won a race either), Zippy started fast and led most of the way. But down the stretch, Black Rifle began bumping with the Zipster; Monserrate is convinced the contact kept Zippy out of the winners circle. Z.C.'s jockey Juan Rohena filed a protest with race officials, but it was quickly denied. 

On September 16, Zippy raced again at Northampton, this time as the favorite at 2-1 odds. The result was much the same; he led at the outset and was neck-and-neck with second-place finisher Miner’s Claim for most of the race. In the home stretch, however, he was overtaken by the eventual winner, Sadler’s Claim, leaving Zippy in the money, but out of the limelight once again.

The 57-year-old Monserrate knew exactly what he was in for when he acquired Zippy five years ago in a trade for an ’88 Ford truck. The temperamental beast was already a resident of Monserrate's stable before the transaction was finalized, so he was aware of Zippy's propensity towards nasty confrontations. “He bit me a couple times,” says Felix matter of factly, although more recently they have reached an uneasy peace. Asked how you control such an animal, Felix shrugs and says, “He's not an easy horse to deal with. My wife and daughter discipline him with a carrot.” 

With few places to race, it's unlikely Zippy will have a chance to threaten the record of Quixall Crossett, the English horse that has lost 98 consecutive starts. While a one-on-one showdown seems like a made-for-TV event, Monserrate believes the chances of that happening are slim to none. Regardless, Zippy always has a place with the Monserrates, who remain unflinchingly optimistic that Zippy will one day strut in triumph. “Even if he doesn't win, he can still live here with us,” says Felix. “He doesn't have to worry about going to the meat market.”

The Legend of Zippy Chippy