Sports fans love a winner. The great teams of the past are remembered forever and the athletes who won the games have their numbers retired and are immortalized in their sport’s hall of fame.
Fans also have a soft spot for the lovable loser, the underdogs who try their best but often come up short.
Upstate New York has such an athlete, a horse named Zippy Chippy, who compiled a 0-100 career record and was banned from many Upstate race tracks.
Despite this, he was named one of “People” magazines most interesting personalities in 2000.
His trainer, Felix Monserrate, summed up Zippy Chippy’s career: “Not everybody can be a winner. He wanna run. He’s always ready to go. But he don’t always go too good.”
He was born on April 20, 1991, in Upstate New York. He was a descendant of the some of the greatest names in horse racing.
He was the great-great-grandson of Bold Ruler, who had fathered Secretariat, and his family tree included such greats as War Admiral, Man O’War and Northern Dancer.
Zippy Chippy, though, did not get any of his predecessor’s greatness.
“From his earliest days, Zippy was his own horse. He never really took to harnesses or saddles. Told to run in one direction, Zippy went the other. He stuck his tongue out at strangers and loped while other horses galloped,” a 2016 New York Post profile said.
At his first race, on Sept. 13, 1994, at Belmont Park on Long Island, he finished eighth out of 10. None of the other horses had the pedigree he had and the winner, D’Moment, who had lost by 47 lengths in his first four races, retired after six races, winning only this one race.
Zippy lost three more times at Belmont before being bounced to the minor leagues of New York horse racing.
At a track in Farmington, he would get a friend.
Trainer Felix Monserrate, from Puerto Rico, traded his 1988 Ford truck for the horse.
He knew Zippy was a “nonstarter,” now 0-20 in his career, but he did not like the way Zippy’s former owner treated him.
“That guy,” Monserrate said, “he push him around and say only bad things about him. So yeah. He got the truck and I got a friend.”
A friend who bit him during their first meeting.
Any of Monserrate’s thoughts that Zippy Chippy’s past performances were due to poor training were quickly forgotten, the horse was “stubborn, playful and lazy.”
“If he didn’t feel like training, which was often, Zippy would ignore the trainer. He’d trash his stall for fun and snatch anything a trainer or handler was holding, chew it up, then give it back,” the New York Post wrote.
His diet consisted largely of cupcakes, popcorn, pizza and ice cream. Doritos with beer was his favorite snack, which he often shared with his trainer.
Occasionally, he would finish in second place, giving his trainer hope that the horse’s pedigree would come through. It never did.
On June 23, 1998, with his imperfect record of 0-85 intact, Zippy Chippy outdid himself at Finger Lakes Race Track in Canandaigua.
In a race with six other horses, Zippy refused to break with the others at the bell.
Monserrate, always his biggest defender, said, “He don’t break so good. That’s all.”
Two weeks later, Zippy did it again, and this time received a 60-day ban at the Finger Lakes track.
When he returned to the track on Sept. 8, the stands were packed despite chilly weather. He again did not charge out of the gate and ran the race in a “laid-back stroll,” finishing last by more than 100 yards.
He was given a lifetime ban at the track.
The story of his suspension and his losing streak ran as a cover story in the USA Today. The horse appeared on Comedy Central and Jay Leno and was becoming something of a cult hero around race tracks. (One bettor placed a $20,000 bet on him.)
Some thought that Zippy was being exploited and took his not running hard as a sign that he did not want to be a racehorse anymore.
Some bettors thought he was “taking up space” and should not be run anymore.
“I love him more because everybody puts him down,” Monserrate said, adding that he thought Zippy “loves to run” and was “real, real happy.”
And he was a still a draw wherever he could appear.
“His determination in the face of overwhelming odds is a story the common man can embrace,” the Syracuse Post-Standard’s Donna Ditota wrote in 2003.
In May 2000, the Rochester Red Wings attracted 2,000 more fans than usual to see Zippy Chippy run a 40-yard dash against one of its players, Jose Herrera. The race was played on ESPN and CNN. (Zippy lost, Herrera crossing the finishing line before Zippy figured out he was supposed to be running.)
In July 2002, Batavia Downs had double the attendance when Zippy appeared.
“People are crazy about him,” track publicity director John Clifford said. “Everybody knows him. Everybody around here knows the name. You ask, “Who won the Kentucky Derby?’ and they’ll hem and haw. But mention the name Zippy Chippy and they say, “That’s the horse that never wins!”‘
He never would. He retired in 2004 with zero wins in 100 races. (He did beat two minor league baseball players, Darnell McDonald in 2001 and Larry Bigbee in 2002.) His career earnings were just over $30,000.
He toured Kentucky to bring attention to safe retirements for racehorses.
His longtime trainer, Felix Monserrate, died in June 2015 of pneumonia and heart issues at the age of 72. He believed that a Zippy Chippy movie should be made.
At last report, Zippy Chippy is on the “board of directors” at the Old Friends at Cabin Creek, a retirement center for racehorses in Greenfield, N.Y.
Send your ideas and curiosities to Johnathan Croyle: Email | 315-427-3958