Unfortunately, the 9-year-old gelding doesn't want to run very hard, and the closest he'll get to May 6's Derby will be if someone installs a TV in his barn. In 86 starts, Zippy Chippy has never won—a Thoroughbred racing record for four-legged futility. "Sometimes he got off to a slow start," says Monserrate, 57. "Sometimes he got tired. One time he went after another horse." That's another problem: Zippy is meaner than an outhouse rat. "He'll bite, he'll kick, he'll chase you out of the stable," says Monserrate, who acquired Zippy in 1995—in a trade for his 1986 Ford van with 80,000 miles on it.
But as Zippy's losing streak has inched up, he has developed a following. "People started to pay attention," says Monserrate, who trains 27 other horses. "They'd say, 'How's Zippy? When is Zippy going to run?' " So many fans were throwing money away that Finger Lakes racetrack banned Zippy "for the protection of the betting public," says track spokesman Rick Coyne. Undeterred, Monserrate raced him in Northampton, Mass., last Sept. 6. The result: Loss No. 86. Still, Monserrate lives in hope. "I still like the way he races," he says. "I still think he can win." Just don't bet on it.
Far from the sound of the starting bugle, Zippy Chippy lives quietly on Felix Monserrate's Upstate New York farm. His grandsire Northern Dancer won the Kentucky Derby and the Preakness in 1964, so Zippy should be a bluegrass blue blood. "He wants to run," says Monserrate, his owner and trainer.