It seemed like a good deal at the time – a rattletrap Ford van with more than 100,000 miles on the odometer in exchange for a promising thoroughbred whose family tree included Man o’ War, Native Dancer and the father of the greatest racehorse of them all – Secretariat.

Felix Monserrate, the Finger Lakes Racetrack trainer who swapped his jalopy for Zippy Chippy in 1995, wasn’t concerned that the thoroughbred had dropped his first 20 races. He chalked up the losing streak to poor training and truly believed he’d bring out the best in Zippy. He felt the racehorse was destined to become well-known, like his iconic ancestors. If ever there was a horse born to run, it was Zippy.

Sadly, Zippy, who died last week at age 31, never did live up to his bloodlines, but he became famous in a way all his own. While Man o’ War, Native Dancer and Secretariat thrilled the masses with dominating victories, Zippy won people over by losing.

He would go zero-for-100 in his thoroughbred career, coming tantalizingly close on rare occasions, with eight second-place finishes and a dozen thirds. Toward the end of Zippy’s career, most tracks banished him because of his penchant for refusing to leave the starting gate once the race commenced. There were other instances of the gelding bolting out of the gate but stopping mid-race. While other horses dreamed of running for the roses, Zippy seemed content to stop and smell and eat the roses.

To say he never won is not accurate, because he did experience the thrill of victory three times. The first occurred during a 2001 exhibition in Freehold, N.J., against a harness racehorse named Paddy’s Lady. Zippy spotted the trotter a 20-length lead and nipped him and his rig by a neck. The other two victories came at Frontier Field in 2001 and 2002 when he defeated Rochester Red Wing outfielders Darnell McDonald and Larry Bigbee, respectively, in 50-yard “man-vs.-beast” sprints across the outfield grass. Those wins 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 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. “The Today Show,” “Good Morning America” and ESPN’s SportsCenter were among the network programs showing highlights.

Zippy wound up losing 70 races at Finger Lakes. The 100th and final defeat of his career occurred on Sept. 10, 2004, at Northampton Fair in Massachusetts – which at the time was one of the few tracks in North America that hadn’t banned him. Fittingly, he finished last.

By that time, he had become a cult figure and an inspiration, with millions of fans following his exploits. Near the end of Zippy’s run, 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 admirer wrote: “God knows there are millions of us who can relate to your struggles.”

No one loved Zippy more than Monserrate, who died seven years ago. He always was able to look beyond his best friend’s recalcitrance and shortcomings. Zippy tested him from the start.

“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 wrote in “The Legend of Zippy Chippy: Life Lessons from Horse Racing’s Most Lovable Loser,” a highly entertaining book published in 2016. “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 the rest of his life. Those teeth marks would serve as a reminder of Zippy’s legendary stubbornness and the bond the two shared.

Zippy retired three months after his final race and had a brief second career as an outrider’s pony guiding horses to the starting gate at Finger Lakes. In order to ensure Zippy would be taken care of for the rest of his days, Monserrate arranged for him to live at Old Friends Thoroughbred Farm at Cabin Creek, near Saratoga Racecourse. While there, Zippy became good friends and paddock mates with Red Down South, a chestnut gelding. He also would continue being a star, attracting hundreds of visitors each year.

“We have horses here that won huge races in their careers, but Zippy’s celebrity trumps them all,’’ Cabin Creek co-owner JoAnn Pepper told me a few years ago. “I think the fact he never won but never stopped battling appeals to people. We all can identify with him.”

That we could. He was a loser who won our hearts.

Best-selling author and nationally honored journalist Scott Pitoniak is the Rochester Business Journal sports columnist.

Great article Scott, never knew about Zippy – I enjoyed leaning about our local celebrity and you told the story in a wonderful way, as always!

Thanks. Much appreciated. Zippy will always be one of my all-time favorite sports personalities.

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