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On Sports

The legendary life of racing's lovable loser Zippy Chippy

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On Sports
Rochester Business Journal
August 26, 2016

Felix Monserrate couldn’t curb his enthusiasm after trading his rattletrap Ford van for the thoroughbred racehorse with the royal pedigree. Yes, it was disconcerting that Zippy Chippy hadn’t won any of his first 20 starts. But Monserrate chalked that up to poor training. He figured a horse whose family tree included Man o’ War, Native Dancer and the father of the greatest thoroughbred of them all—Secretariat—was destined to become as well known, perhaps even better known, than his famous ancestors. If ever there was a horse born to run, it was Zippy.

“After waving goodbye to his van, Felix went into the barn as the new and proud owner of Zippy Chippy, a horse that had nowhere to go but up,” humorist William Thomas writes in “The Legend of Zippy Chippy: Life Lessons from Horse Racing’s Most Lovable Loser,” his entertaining new book. “By way of offering his opinion of the trade, the horse immediately bit him.”

Monserrate would bear the scars from that chomping on his back for the rest of his life. (In his never-ending quest to be a contrarian, Zippy bit the back rather than the hand that fed him.) Those teeth marks would serve as reminders of the thoroughbred’s legendary stubbornness, a trait that would exasperate his trainer time and time again. But Zippy’s desire to stop and smell the roses (occasionally during races) rather than run for the roses also would endear him to Monserrate and the horse’s legion of fans. The more Zippy lost, the more people loved him. He clearly didn’t subscribe to Hall of Fame football coach Vince Lombardi’s mantra that “winning isn’t everything; it’s the only thing.” In Zippy’s case, winning was a never thing. And he was quite content with that.

In 100 races against thoroughbreds—including 70 at Finger Lakes Racetrack, 20 miles southeast of Rochester—Zippy never crossed the finish line first. He came close on several occasions with eight second-place finishes and a dozen thirds. Toward the end of his racing career, it got so bad that tracks banished him because he refused to leave the starting gate.

To say the Zipster never won isn’t totally accurate. He did experience the thrill of victory in a 2001 exhibition against a harness race- horse named Paddy’s Lady. Zippy spotted the trotter a 20-length lead and nipped him and his rig by a neck. He also notched wins at Frontier Field in 2001 and 2002 when he defeated Rochester Red Wings outfielders Darnell McDonald and Larry Bigbee, respectively, in 50-yard, “man-vs.-beast” sprints across the outfield grass. Those victories were preceded by a loss to outfielder Jose Herrera in the first “Red Wing Derby” on Aug. 17, 2000, in a 40-yard dash. “If Herrera had to carry a jockey,’’ grumbled Finger Lakes handicapper Dave Mattice, “it would be more fair.” Monserrate insisted that his gracious horse had allowed his two-legged opponent to win.

The races against the ballplayers added to Zippy’s burgeoning popularity by attracting national media attention. People magazine named him one of the world’s most interesting personalities in 2000, and Baseball America called the race against Herrera the year’s top promotion in minor-league baseball. ESPN, “The Today Show” and “Good Morning America” showed race highlights.

Thomas’ humorous and at timespoignant book ultimately is a love story between a man and his horse. Monserrate had moved to the United States from Puerto Rico at age 20 to pursue his career in racing. Many trainers live by the motto that it is better not to fall in love with a horse because you eventually may have to sell, trade or euthanize it. But Monserrate was not like other trainers. He loved Zippy like a member of the family, even though the horse occasionally tortured him.

There’s a story about how Zippy refused to practice one day, holding his trainer captive in the barn for several hours. On another occasion, the horse grabbed a mouthful of Monserrate’s shirt and playfully dangled the trainer in midair, prompting his fellow track workers to laugh lustily. After a few minutes, Zippy let him down. Monserrate brushed off the incident, saying, “He’s a strong horse. He can hold you for a long time.”

Monserrate was always able to look beyond Zippy’s recalcitrance and shortcomings. “Say you have three children,” he explained. “One is a lawyer, doing well. The other, a doctor, very, very successful. But the third one, not so smart, so he’s working at McDonald’s. What do you do? Ignore him? Course not. He’s the one who needs your help. That’s Zippy.”

Over time, the thoroughbred became a cult figure. And an inspiration. One day Monserrate received a humungous Hallmark card from a group of fans in New Jersey. One of the inscriptions read: “The key to a true winner is that you keep on trying.” Another wrote: “God knows there are millions of us who can relate to your struggles.”

Sadly, Monserrate didn’t get a chance to read Thomas’ finished manuscript. The trainer died last year from heart problems and pneumonia at age 72. Zippy, meanwhile, is 25 and living the good life at Old Friends at Cabin Creek, a farm for retired thoroughbreds, 15 miles east of the famed Saratoga Race Track, where the prestigious Travers Stakes will run tomorrow.

“We have horses here that won huge races in their careers, but Zippy’s celebrity trumps them all,” says farm owner JoAnn Pepper. “I think the fact he never won but never stopped battling appeals to people. We all can identify with him.”

When Monserrate traded his jalopy for Zippy in 1995, he believed he had acquired a horse on the fast track to greatness. It didn’t work out exactly how he envisioned, but Zippy is now immortalized in a book and one day may be portrayed in a movie. Monserrate told Thomas that he had collaborated with a screenwriter from Los Angeles several years ago. “He’s the neighbor of the guy who made the movie about the other horse,” he told Thomas. That “other horse” was Seabiscuit, an undersized, overachieving thoroughbred who was America’s darling during the Great Depression and whose story became a box-office smash that was nominated for seven Academy Awards. “He thinks my horse is a better story,” Monserrate said.

He just might be right.

Best-selling author Scott Pitoniak is the Rochester Business Journal sports columnist.

8/25/2016 (c) 2016 Rochester Business Journal. To obtain permission to reprint this article, call 585-546-8303 or email

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