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Read Zippy's poem by Bill Littlefield, host of NPR's "It's Only a Game" here: ZIPPY CHIPPY

Born April 20, 1991 by Compliance out of Listen Lady by Buckfinder
Zippy Chippy is a wonderful NY bred gelding. Zippy’s greatest accomplishments in racing are perhaps not accomplishments at all. But what made him stand out among the numerous other losers in the industry was the fact that he lost 100 times, making him one of the most losing horses in the history of horse racing. His losing streak made him famous; so famous that he had a following: people who would go to all his races, some hoping for the streak to end, and others just looking to see how long he would go on losing. For the optimists who hoped for a winning race, that dream never came true. Of all 100 races, Zippy didn’t win one. The reason this happened was because his owner/trainer, Felix Monserrate, had an emotional attachment to the losing horse, which he had traded an old pick-up truck for. In order to keep Zippy, Felix raced him in races that were too hard for him to win, and didn’t race him in claiming races so that he wouldn’t get claimed. Zippy could be quite a troublemaker at the track though. He was known to sometimes stop in the middle of races, not leave the gate, bite, etc. This caused him to be banned from every track in America, besides the Northhampton Fair in Massachusetts. After his retirement, Felix kept him for a few years until he decided Old Friends was the perfect place for a horse like Zippy. Zippy did make money at the track. In total, Zippy’s record was (0-8-12) from 100 starts and earnings of $30,834. He now lives happily with his best friend, Red Down South. Zippy was bred by Caprituar Farm, and owned/trained by Felix Monserrate.

It was a sad, beautiful day, celebrating the life and times of Zippy Chippy. As we stood around sharing stories… he became bigger than life, he made us laugh and cry, just like he did when he was here. So thankful for all the crazy memories and all the friends made. I think even Steve Hartman (On the Road with) was amazed at what a horse could mean to so many people. The Zipster has passed but his legacy will live forever as he continues to fulfill his mission as an ambassador for aftercare.
Cheers Zippy… Thanks for everything ❤️

Zippy Chippy's Racing Record:

  • Earnings: $30,834

  • Starts: 100

  • Firsts: 0

  • Seconds: 8

  • Thirds: 12

Photos of Zippy Chippy