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The Legend of Zippy Chippy: Life Lessons from Horse Racing's Most Lovable Loser
From acclaimed humorist William Thomas comes the funny yet poignant story of a thoroughbred racehorse that lost 100 races in a row -- but, in everyone's eyes, became the ultimate winner.On April 20, 1991, at Capritaur Farms in Upstate New York, Zippy Chippy strolled into the world. He was born from American horse racing royalty -- Compliance (his father was Kentucky Derby-winner Northern Dancer; his great-grandfather Native Dancer, the Preakness and Belmont Stakes winner) and Listen Lady (great-granddaughter of Native Dancer). Even before his birth, the hopes (not to mention the bill for his planned production) for Zippy Chippy were high. His pedigree was horse racing Northern Dancer, Man o' War, Count Fleet, Bold Ruler, War Admiral, and Buckpasser were all ancestors. His success and glory seemed inevitable. But moments after his birth, Zippy Chippy struggled to his feet, took two steps forward . . . and stopped dead in his tracks. He looked around, took in his surroundings, maybe indulged in a little daydream, then promptly lay down for a nap in the straw. And thus began Zippy Chippy's storied racing career. Vince Lombardi, one of the greatest NFL coaches of all time, famously said, "Winning isn't everything, it's the only thing." These words have become the battle cry of athletes, coaches, and teams everywhere, but over the years, sports have taken on a literal interpretation of Lombardi's mantra. Match-fixing, doping, sabotage, cocky and mean sportsmanship, all in the name of winning, have infiltrated and scandalized games, teams, reputations, and newspaper headlines. Yet, since his first moments in the world, Zippy Chippy ignored Lombardi and turned his nose at the concept of winning-at-all-costs. In fact, he decided to not win at all, losing, over the course of his career, 100 consecutive races, at some of the greatest tracks in the Belmont Park, Aqueduct, Finger Lakes, and Suffolk Downs among them. And he did so with his owner, Felix Monserrate, by his side -- a man who refused to sell Zippy, or even retire him, simply because he couldn't come in first. Soon, Zippy's cheering squad grew to include people who, enchanted by his story, would travel from all over North America to watch him lose but then happily gallop back to his stable. To them, Zippy Chippy was just like them; someone who wasn't an athlete with a million-dollar contract, or someone with movie star looks -- he was a creature who struggled, who lost, and who failed even the lowest of expectations. But, somehow, he found a way to enjoy himself and eagerly return for the next race. Told with laugh-out-loud wit and a lot of heart, The Legend of Zippy Chippy is the story of the losing-est racehorse in North American history -- a perpetual loser who would become the winning thoroughbred in professional horse racing to steal peoples' hearts.
- GenresAnimals
308 pages, Kindle Edition
Published April 5, 2016
5 people are currently reading
59 people want to read
About the author
William Thomas
124 books4 followersWilliam "Bill" Thomas works as a business intermediary and attorney in, both, New York and Florida. He specializes in selling businesses and commercial properties in South Florida. Being both an attorney and a broker gives Mr. Thomas a competitive edge that has proven to be of great benefit to his clients. He is highly respected and trusted within the South Florida business community.
Bill currently runs The Beech Group which is the M&A division of Florida Business Brokers, a highly successful business brokerage. He has 25 operating agents throughout Florida that have gone through his training program, and he is working on a book to help other business advisors train their agents to become successful business broker agents.
Bill's niche is upper main street and middle market business sales (with sales revenues over $1MM). He is able to accomplish a high percentage of deals due to his focus on organization and preparation. His sales model starts with doing the due diligence for his sellers prior to making a strategic decision to sell and prior to creating a pricing model for the merger. His preparedness allows him to maintain a closing ratio above 83% compared to the industry average of 22% for business brokers. Business owners looking to retire may feel free to call or email Bill Thomas for a free business sale consultation at (561) 914-1182, William@FloridaBizMLS.com.
Bill currently runs The Beech Group which is the M&A division of Florida Business Brokers, a highly successful business brokerage. He has 25 operating agents throughout Florida that have gone through his training program, and he is working on a book to help other business advisors train their agents to become successful business broker agents.
Bill's niche is upper main street and middle market business sales (with sales revenues over $1MM). He is able to accomplish a high percentage of deals due to his focus on organization and preparation. His sales model starts with doing the due diligence for his sellers prior to making a strategic decision to sell and prior to creating a pricing model for the merger. His preparedness allows him to maintain a closing ratio above 83% compared to the industry average of 22% for business brokers. Business owners looking to retire may feel free to call or email Bill Thomas for a free business sale consultation at (561) 914-1182, William@FloridaBizMLS.com.
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Displaying 1 - 11 of 11 reviews
July 27, 2025
This is one of those books I bought ... long before I discovered the Internet Archive. I definitely wished I read this there instead of buying a used copy on eBay.
After the copyright page and rather dubious dedication, there's Zippy Chippy's pedigree page. And on that page was a special note -- that Native Dancer was the 1953 Triple Crown winner.
Oh fucking no.
Perhaps on some other alternate universe Native Dancer overcame his bad luck to become the 1953 Triple Crown winner. He certainly deserved to be. He would wind up having the most impact on the Thoroughbred since the Darley Arabian (who probably wasn't an Arabian.) Depending what source you read, almost all Thoroughbreds alive today trace their ancestry back to Native Dancer through his sons Raise a Native and Northern Dancer. Zippy Chippy traces to Native Dancer through his sire and dam.
There's a lot of puns, obvious jokes you can see coming a mile away, and other literary shenanigans for the first 35 pages.
And then it all comes to a screeching halt on page 36, when it's revealed that one of Zippy Chippy's owners purposefully bought him to slaughter him.
It's very rare that in books about horse racing does the truth about what happens to slow horses is printed. Even stakes winners -- even Kentucky Derby winners -- get sold for slaughter when their owners can't get any more money out of them.
The book doesn't really get going until about page 60. That carries on for a read that was much faster than Zippy himself until it's time for Zippy to retire. Then, it's about 50 pages too long as Thomas just can't seem to let a subject go.
Granted, Thomas is a humor writer, a sometime sports writer, and not a horse race historian. But still, the book could've been so much better. There could've been more focus on horse racing and horses rather than comparing just about everything in sports and Thomas' past life to Zippy Chippy. Thomas reveals the biggest problems in horse racing, like officials who clearly are on the take as well as killing horses for profit, and yet goes no further to investigate these things. He even says that you should take the family for a fun day at the races, to fuel an industry that deserves to vanish.
It winds up being a very unfunny book.
Zippy Chippy was in his 20s when this book was published. He'd live to be 30.
After the copyright page and rather dubious dedication, there's Zippy Chippy's pedigree page. And on that page was a special note -- that Native Dancer was the 1953 Triple Crown winner.
Oh fucking no.
Perhaps on some other alternate universe Native Dancer overcame his bad luck to become the 1953 Triple Crown winner. He certainly deserved to be. He would wind up having the most impact on the Thoroughbred since the Darley Arabian (who probably wasn't an Arabian.) Depending what source you read, almost all Thoroughbreds alive today trace their ancestry back to Native Dancer through his sons Raise a Native and Northern Dancer. Zippy Chippy traces to Native Dancer through his sire and dam.
There's a lot of puns, obvious jokes you can see coming a mile away, and other literary shenanigans for the first 35 pages.
And then it all comes to a screeching halt on page 36, when it's revealed that one of Zippy Chippy's owners purposefully bought him to slaughter him.
It's very rare that in books about horse racing does the truth about what happens to slow horses is printed. Even stakes winners -- even Kentucky Derby winners -- get sold for slaughter when their owners can't get any more money out of them.
The book doesn't really get going until about page 60. That carries on for a read that was much faster than Zippy himself until it's time for Zippy to retire. Then, it's about 50 pages too long as Thomas just can't seem to let a subject go.
Granted, Thomas is a humor writer, a sometime sports writer, and not a horse race historian. But still, the book could've been so much better. There could've been more focus on horse racing and horses rather than comparing just about everything in sports and Thomas' past life to Zippy Chippy. Thomas reveals the biggest problems in horse racing, like officials who clearly are on the take as well as killing horses for profit, and yet goes no further to investigate these things. He even says that you should take the family for a fun day at the races, to fuel an industry that deserves to vanish.
It winds up being a very unfunny book.
Zippy Chippy was in his 20s when this book was published. He'd live to be 30.
February 13, 2018
Born under most auspicious circumstances (descended from War Admiral, Native Dancer, Man ‘O War, to name a few luminaries) Zippy Chippy never quite panned out...In fact, he never won. Zippy Chippy lost 100 races, with only a few second and third place finishes in a career spanning over 11 years.
But to thousands of fans, it didn’t matter. Zippy Chippy was a champion.
The Legend of Zippy Chippy traces that horse and his people, notably his trainer, Felix, who loved him like a son. And the author finds that there is much to be learned from someone like Zippy, who people could relate to, because of the way he handled constant defeat.
Zippy Chippy was a cranky horse, likely to bite the people he loved and steal the hats of anyone else. But he was special because he was like the rest of us, who also can be cranky and maybe steal a hat once in a while and (let’s face it) are more familiar with defeat than victory. He had all the desire in the world, but he just found so many ways to lose.
But throughout it all, he kept his head up and won the hearts of fans, who often bet on him even though they knew it was no more than a symbolic bet for the underdog (albeit, a poorly priced one—if he ever had come in he would have likely only paid a few dollars since the odds on him were inflated and had little to do with his actual ability to win).
This is a fun book that explores a mildly dark side of horseracing. It is similar to another book I liked about horseracing: Elizabeth Mitchell’s Three Strides Before the Wire, about the great and tragic champion, Charismatic…only this is the exact opposite, in that the hero is a loser. A record setting, wonderful loser.
Really good, easy to read, told with humor, this is a book I will happily return to my friend who loaned it to me. It’s only been a year…
But to thousands of fans, it didn’t matter. Zippy Chippy was a champion.
The Legend of Zippy Chippy traces that horse and his people, notably his trainer, Felix, who loved him like a son. And the author finds that there is much to be learned from someone like Zippy, who people could relate to, because of the way he handled constant defeat.
Zippy Chippy was a cranky horse, likely to bite the people he loved and steal the hats of anyone else. But he was special because he was like the rest of us, who also can be cranky and maybe steal a hat once in a while and (let’s face it) are more familiar with defeat than victory. He had all the desire in the world, but he just found so many ways to lose.
But throughout it all, he kept his head up and won the hearts of fans, who often bet on him even though they knew it was no more than a symbolic bet for the underdog (albeit, a poorly priced one—if he ever had come in he would have likely only paid a few dollars since the odds on him were inflated and had little to do with his actual ability to win).
This is a fun book that explores a mildly dark side of horseracing. It is similar to another book I liked about horseracing: Elizabeth Mitchell’s Three Strides Before the Wire, about the great and tragic champion, Charismatic…only this is the exact opposite, in that the hero is a loser. A record setting, wonderful loser.
Really good, easy to read, told with humor, this is a book I will happily return to my friend who loaned it to me. It’s only been a year…
December 29, 2021
This book details the life of a race horse, Zippy Chippy, who ended up in the Guinness Book of World Records. Given he had a stellar ancestry, including Northern Dancer, Man o’ War, Count Fleet, Bold Ruler, Native Dancer, and War Admiral, you might be thinking that he won a record number of races, but you would be wrong; he lost a record number of races—100, to be exact. As his trainer said once, “My horse, he come second twice in a row!” And that was high praise for Zippy Chippy! He even had 2 races against athletes and lost one of them! Despite his losses, or perhaps because of them, he developed a real following. One funny thing about this is that because so many people bet on him the odds kept changing so that he was not considered a “long-shot”, even though he never won. Very strange system, I think.
Zippy was temperamental, and handlers would only feed him with food at the end of a rake. And he would kick and bite regularly. So when the owner’s daughter, Marisa, 7-years-old, was found in the stall with the horse Dad was very, very, worried. He was quite surprised to see the horse playing cheerfully with the little girl – I guess he could sense a “foal” ☺ It was a fun read – it was amazing that a whole book could be written about a horse that lost so many times.
When the author went into a McDonalds to meet the owner and the owner didn’t show up on time he asked to use a phone. The kid at the counter handed over a phone and said “Don’t call Canada.” “How’d you know I was Canadian?” “You’ve thanked me three times already, and you haven’t even ordered anything.” The author found a way of making everything in the story very amusing – a nice light read.
Zippy was temperamental, and handlers would only feed him with food at the end of a rake. And he would kick and bite regularly. So when the owner’s daughter, Marisa, 7-years-old, was found in the stall with the horse Dad was very, very, worried. He was quite surprised to see the horse playing cheerfully with the little girl – I guess he could sense a “foal” ☺ It was a fun read – it was amazing that a whole book could be written about a horse that lost so many times.
When the author went into a McDonalds to meet the owner and the owner didn’t show up on time he asked to use a phone. The kid at the counter handed over a phone and said “Don’t call Canada.” “How’d you know I was Canadian?” “You’ve thanked me three times already, and you haven’t even ordered anything.” The author found a way of making everything in the story very amusing – a nice light read.
May 18, 2021
The horse that tried and tried, a great story and ending
January 3, 2023
Somewhat repetetive but a great read! Good for a giggle!!!!!!!!
January 31, 2017
The second author at the January Grimsby Author Series event was William Thomas. He wrote Zippy Chippy: Life Lessons from Horse RAcing’s Most Lovable Loser. I have to be honest, that I was struggling with the book. I enjoyed the underlying story but was bogged down with the details about his lineage, other horses and racing in general. Whatever I may have thought prior to the talk, I was refreshed to hear William Thomas speak – he was funny, engaging and so enthusiastic about his book and this horse that I went home to finish the book with a fresh perspective.
Thomas had been in a bar when he first heard the story of Zippy Chippy. As he listened, he asked where he could find the book. There wasn’t one so he began his research and wrote the story. The day the book launched, it sold out on amazon!
The story of Zippy Chippy is unique. He had a strong genetic history of winners. As an individual who had not thought of horse racing since voraciously reading the Black Stallion series (or anything about horses) as a teen, I did recognize the names of Northern Dancer and Man O’War in his family tree. The owner had been hopeful that his DNA would lead to first place finishes but, unfortunately for his original owners, Zippy loved to race but could not finish first. After 6 losses, he was traded to Felix Monserrate – for an old truck!
Felix was an ambitious horse trainer and came to love the horse who definitely had a mind of his own. He would pin people in his stall, bite them, steal hats and steal donuts (if people walked to close to his stall) yet had a special relationship with Felix’s young daughter. He ran to his own standards, slowing to bite an opponent or taking the wide side of the track to avoid bumping into others. He loved to race and even after disappointing finishes was proud of his accomplishments. In the world of racing, most owners would have sold him (sadly he might have ended auctioned off to a glue factory) but Felix had a special place in his heart and continued to race this beast for 100 races! He never won one against another horse. He did, however, succeed in beating a baseball player in an exhibition race.
He may not have come first, but he did win the hearts of fans. They would bet on Zippy when odds were strongly against him. He had a fan club. T-shirts and mugs were sold. Fans came to watch him race and rooted for the underdog! He still has his followers now that he has retired to Old Friends at Cabin Creek where he has inseparable from his pal, Red Down South. He makes more money in retirement than he ever did in racing making “enough money to support 22 other horses who were winners” at the retirement farm!
William Thomas clearly loves horse racing. He spent hours “playing the ponies” in Fort Erie when he was a student and shared that racing is a dying sport (Zippy will likely outlive the Finger Lakes track which banned him). He had a great sense of humour and had the audience laughing about the creative names of race horses such as 50 Shades of Hay or Another Horse. He said that he would never have called this horse Zippy Chippy but would have named him Crazy Ass!
Thomas had to audience considering the societal pressures to win at all costs. Zippy provided a lesson about perseverance and never giving up. He feels that the real message should be that “failure is not losing, failure is how we learn to win” and that we need to teach our kids to “fail better”. He pointed out that “life is not about the trophy but about the trying” and that we all need to “bounce back” from failure. Great messages for kids! The author’s new motto came from Felix: “losing real close is plenty close enough”!
If you get a chance to listen to William Thomas, he is a great speaker and with a comedic sense of humour. He had high praise for the Grimsby Author Series and had hosted a similar series in Port Colborne. If you are interested in more details about Zippy Chippy, watch for a stage play and movie which are to be made about him.
Thomas had been in a bar when he first heard the story of Zippy Chippy. As he listened, he asked where he could find the book. There wasn’t one so he began his research and wrote the story. The day the book launched, it sold out on amazon!
The story of Zippy Chippy is unique. He had a strong genetic history of winners. As an individual who had not thought of horse racing since voraciously reading the Black Stallion series (or anything about horses) as a teen, I did recognize the names of Northern Dancer and Man O’War in his family tree. The owner had been hopeful that his DNA would lead to first place finishes but, unfortunately for his original owners, Zippy loved to race but could not finish first. After 6 losses, he was traded to Felix Monserrate – for an old truck!
Felix was an ambitious horse trainer and came to love the horse who definitely had a mind of his own. He would pin people in his stall, bite them, steal hats and steal donuts (if people walked to close to his stall) yet had a special relationship with Felix’s young daughter. He ran to his own standards, slowing to bite an opponent or taking the wide side of the track to avoid bumping into others. He loved to race and even after disappointing finishes was proud of his accomplishments. In the world of racing, most owners would have sold him (sadly he might have ended auctioned off to a glue factory) but Felix had a special place in his heart and continued to race this beast for 100 races! He never won one against another horse. He did, however, succeed in beating a baseball player in an exhibition race.
He may not have come first, but he did win the hearts of fans. They would bet on Zippy when odds were strongly against him. He had a fan club. T-shirts and mugs were sold. Fans came to watch him race and rooted for the underdog! He still has his followers now that he has retired to Old Friends at Cabin Creek where he has inseparable from his pal, Red Down South. He makes more money in retirement than he ever did in racing making “enough money to support 22 other horses who were winners” at the retirement farm!
William Thomas clearly loves horse racing. He spent hours “playing the ponies” in Fort Erie when he was a student and shared that racing is a dying sport (Zippy will likely outlive the Finger Lakes track which banned him). He had a great sense of humour and had the audience laughing about the creative names of race horses such as 50 Shades of Hay or Another Horse. He said that he would never have called this horse Zippy Chippy but would have named him Crazy Ass!
Thomas had to audience considering the societal pressures to win at all costs. Zippy provided a lesson about perseverance and never giving up. He feels that the real message should be that “failure is not losing, failure is how we learn to win” and that we need to teach our kids to “fail better”. He pointed out that “life is not about the trophy but about the trying” and that we all need to “bounce back” from failure. Great messages for kids! The author’s new motto came from Felix: “losing real close is plenty close enough”!
If you get a chance to listen to William Thomas, he is a great speaker and with a comedic sense of humour. He had high praise for the Grimsby Author Series and had hosted a similar series in Port Colborne. If you are interested in more details about Zippy Chippy, watch for a stage play and movie which are to be made about him.
May 16, 2016
Story of thoroughbred race horse, Zippy Chippy, with a great pedigree but didn't exactly live up to it on the race track. He races 100 times, never coming up with a win! This book is his story and the story of his owner/trainer Felix Monserrate and family who love this rascal with all their hearts. You will love this story written so humorously by William Thomas. Even people who don't like horse racing will get a kick out of this story.
October 16, 2016
This was one of the best feel good stories I've read in a long time. It's uplifting for the human spirit and wonderfully funny. The author uses analogies to sports stories to help readers understand how and why this horse does not give up. It is well written, an easy read and a book that you don't want to put down. You will not be disappointed if you buy this book and share it with your family.
I can hardly wait to read another one of William Thomas's books.
I can hardly wait to read another one of William Thomas's books.
December 31, 2016
Love love love this book! The author writes with much humor and this a wonderful book about a very special horse. If you love an underdog,you will love this book!!
September 9, 2024
A easy does it book about a horse trainer/and horse.
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April 14, 2017An interesting read for several reasons (including the upcoming visit at the library from the author): there are many local connections here, and I remember sports radio show host Bob Mathews talking about this horse in the 90s; the horse is a character...as is his owner; there are life lessons related to the story; and there are funny sports-related themes throughout. Definitely a niche book that should have some following in western New York.
Displaying 1 - 11 of 11 reviews