Once upon a time, there was a horse named Zippy Chippy. But only once.

If you look at his record, zero wins in 100 races, you might think he just lived to lose. Rather, this racehorse loved to be himself more than anything else and that desire to do things his way always made him a beloved figure on the track and off.

Our first instinct whenever considering a racehorse of note is to look at the pedigree. Of course, Zippy Chippy had no shortage of that. His sire, Compliance, was one of 16 foals produced the mare Sex Appeal, who also is the dam (mother) of El Gran Senor, the 1984 Two Thousand Guineas and Irish Derby winner; and Try My Best, a champion miler in Ireland. By Northern Dancer, Compliance was stakes-placed in Ireland and then stood at stud in New York, where he also sired Fourstardave and Fourstars Allstar. Zippy Chippy’s dam, Listen Lady, was a granddaughter of Hall of Famer Buckpasser, giving the New York-bred a foundation that promised something special.

Zippy Chippy at Finger Lakes in 1998 (BloodHorse Library)

He was born on April 20, 1991, at Capritaur Farm in upstate New York, arriving all brown except for a white diamond on his forehead. As author William Thomas described his arrival in his book on the horse, he “struggled to his feet, took two steps, and stopped,” standing as if he were taking in his surroundings for a few minutes and then laid down for a nap. As he grew, Zippy Chippy went through the usual racehorse education, learning how to wear a saddle and bridle, work with a rider, and gallop around the racetrack. Even as a young horse, though, he was not shy about sharing his personality, sticking out his tongue, smiling when he saw a camera, and running in the opposite direction when out in the field with his fellow trainees.

Nevertheless, Zippy Chippy became a racehorse in the colors of Charles Frysinger, a businessman from Ohio who bought the gelded son of Compliance from a New York man who created Thoroughbred investment packages for those looking to break into ownership. Unraced at age 2, he made his debut on Sept. 13, 1994, going 6 ½ furlongs on the Belmont Park main track for trainer Carl Domino, and finished eighth. He tried again 10 days later in a seven-furlong maiden race and improved to third. By the end of his first season of racing, Zippy Chippy had started 11 times and finished third three times, earning $9,813 in the process.

After 18 starts with zero wins, Frysinger gave up on Zippy Chippy. After racing at Belmont Park and Aqueduct, the gelding had tried his luck at Finger Lakes before dropping to the claiming ranks at Suffolk Downs, and the owner, who had never even met the horse or seen him race, sold Zippy Chippy to Michael Barbarita, who supposedly owned him for three starts. However, the person who truly had the gelding in his possession was a groom named Louis. But keeping a horse was expensive, and Louis was about to move from upstate New York to Florida. He could not take Zippy Chippy with him and was considering disposing of the horse. When trainer Felix Monserrate heard about Louis’s plan, he was dismayed. Despite being 0 for 21, Zippy Chippy still loved his job. He did not seem discouraged by losing. Monserrate saw himself in the horse and could not stand the idea of Louis sending the gelding to slaughter. So, he traded the relocating groom his truck for the horse, and the trainer and his family, including partner Emily Schoeneman and their kids Marisa and Jared, brought home a racehorse unlike any other.

What did Zippy Chippy do to thank his new owner for believing in him enough to barter for him? He bit him. It was indicative of what the gelding had become: a scamp. He liked to steal things out of the hands of or off the heads of passersby. He liked to kick his water bucket around like a soccer ball. He also proved to be a snacker, eating everything from donuts to Doritos. Besides the snacks, the only person he seemed to like was Marisa; Zippy Chippy even grabbed Monserrate by the shirt and lifted him off the ground. He also trapped the trainer in his stall for an hour, with the erstwhile conditioner only escaping because a groom was able to distract the horse with some alfalfa so Monserrate could escape. 

Zippy Chippy enjoying a snack at Old Friends (Old Friends photo)

Throughout all of the shenanigans, Zippy Chippy kept racing and, well, losing. No matter what his owner-trainer tried, the gelding’s win count stayed at zero, and in the process, he gained a following. That translated to people showing up at the racetrack, which led to attention from the media, but not always the most flattering kind.

Monserrate tried giving the gelding some time off to see if that would help him find his form, but all Zippy Chippy did was sulk. It was clear that the horse loved the track, the racing, and even, begrudgingly, his human family, but still he did not find the winner’s circle. That led to an appearance in a 2000 issue of People magazine’s list of most interesting personalities and stunts like racing a minor league baseball player for 40 yards (he lost) and then against a trotter, which he won even while spotting him 20 lengths. He also beat another minor league player in a second match race, this one at 50 yards.

By 2004, when he was 13 years old, Zippy Chippy had been racing for 11 seasons. He logged his 100^th start on Sept. 10, finishing last in an eight-horse field at the Northampton Fair in Massachusetts. He went on to become a stable pony and a pet for Marisa and her family. Long term, Monserrate was going to keep him; never would Zippy Chippy meet an unfortunate fate. But then Michael Blowen of Old Friends came along and made him an offer he could not refuse: Zippy Chippy would be the centerpiece of Old Friends’ new sanctuary at Cabin Creek near Saratoga Springs, N.Y. There, Zippy Chippy was the star attraction for 12 years. He even inspired a book by Thomas as well as a children’s book by Artie Bennett.

On April 15, 2022, Zippy Chippy breathed his last, but while he left this world winless, he really showed everyone that he was the biggest winner of them all. Beloved, he attracted thousands of fans to Old Friends at Cabin Creek and helped other horses find a soft landing in their paddocks. As Frank Sinatra once sang, he did it his way, turning the life of a racehorse on its head and showing us all that the best part of life is more than winning: it’s living your days on your terms.