Legendary Canadian race horse Northern Dancer's grandson Zippy Chippy was famous for all the wrong reasons

The Legend of Zippy Chippy comes to life in a new book by Canadian author William Thomas (Courtesy: Penguin Random House)
The Legend of Zippy Chippy comes to life in a new book by Canadian author William Thomas (Courtesy: Penguin Random House)

Horse racing.

The sport of kings.

Well not exactly.

The late Felix Monserrate, a salt of the earth type and his horse Zippy Chippy would turn that term inside out and upside down.

Lurking amongst the names of legendary thoroughbreds owned by the well-heeled such as Affirmed, Secretariat and 2015 Triple Crown winner American Pharoah is Zippy, who rose to fame for all the wrong reasons.

Born in 1991 at Capritaur Farms in upstate New York, Zippy never won a race against a fellow thoroughbred in 100 attempts over the duration of his career which lasted from 1994-2004.

While his futility is shocking even when considering that other horses have fared slightly worse, Zippy’s story is compounded by the fact that his bloodlines can be traced back to iconic stock like War Admiral (Triple Crown winner 1937) and Native Dancer (who won 21-of-22 races including the Preakness and Belmont Stakes in 1953), just to name a few.

How could this cantankerous yet fun-loving prankster, whose grandfather was none other than the king of Canadian horse racing and prolific stud – Northern Dancer, be known more for hijinks like eating a pizza and the box it was delivered in, or being acquired by Monserrate for used Ford truck, as opposed to standing in the winner’s circle even just once?

As author William Thomas, a Canadian humorist, explains it with a healthy dose of sarcasm, “Horse breeding is not an exact science.”

That sums up the legend of an imperfect horse – perfectly.

Thomas recently sat down with Eh Game in Toronto to discuss his new book, “The Legend of Zippy Chippy, Life Lessons from Horse Racing’s Most Lovable Loser.”


Eh Game:  It seems that you and Zippy Chippy were destined to come together. You are from the Niagara region (in relative proxmity to where Zippy was born and bred), went to the track starting at an early age and are a humor writer.  Do you think you were destined to write this book?

William Thomas:  I have never been asked that question but yeah I guess those two paths were meant to meet at some point.  Yeah, I look for humor everywhere.

EG: Describe the initial a-ha moment when you knew this book need to be written?

WT: I’m a hiker.  When I finish a hike, I want a beer and I got into a bar down in Canandaigua, NY., and the track is right there so horses came up (in conversation with another patron).  I started talking about (1973 Triple Crown winner) Secretariat, I get chills up my spine thinking about  Secretariat.  I remember him saying we have the Secretariat slash opposite here.  I said, “What the hell is that?” and he said, “Have you ever heard of Zippy Chippy?” I said, “No.”, and he started telling me the stories.  I said, “That’s the kind of book I want to read, where can I buy the book?”  He said, “There is talk of a movie but I don’t think there is a book, phone (owner) Felix (Monserate).”

EG:  How long did it take you to write this book?

WT: The whole project took three years from 2013-15.  In 2014, I got on a plane, put all the stuff (related to writing the book) in a suitcase, rented a tiny little apartment in the south of Portugal -  31 days, it rained everyday – perfect, I couldn’t go out, so I came back with the first draft.  It was about another year here working with the editor. We revised this thing, some were light revisions but I re-wrote this eight or nine times.”

EG:  Zippy first began racing in 1994, how did you recreate all of his old races? You describe them as though you were there.

WT:  Two ways.  (Felix gave me) a bag with every program, every clipping, some videotape.  He gave me the whole thing, I was just flattered.  I said, “I’m so flattered that you trust me.”  He said, “I know where you live.”

Also, is wonderful.  If you go on Equibase and punch in a horses’ name, it will show you pretty much, not going back as far as Secretariat – not into the 1970’s but I’m thinking mid-eighties to now, it will show you every race the horse ran, every place he came, the money, the day, the track, the conditions and the comments from the official handicapper – died early, went wide etc.

So you start piecing this together with the (old newspaper) clippings and you pretty much got what’s going on.

EG:  Amongst the lovable losers mentioned in the book is Eddie “The Eagle” Edwards.  A movie just came out about him and it is (at time interview) running at roughly an $8 million loss.  Would it be only fitting if Zippy’s movie did the same?

WT:  Only if it lost $81 million. I knew immediately that this book needed big, big hunks of humor, that’s why those breakers are in there (short anecdotes about other laughable underdogs like Edwards), to break up Zippy's losing (streak).  I like some of these, they sort of fit in with Zippy and (are) full value entertainment for those that are not the best at their sport.

EG:  Are you in the process of selling the screen rights?  You mentioned some inquires.

WT:  Yeah, just two inquiries, I wrote movies for CBC, so I know how it works.  There is never going to be a movie, but there might be an option deal.  It’s so hard to make a movie these days.

EG:  Zippy won just over $30,000 in his career.  What do you estimate it cost Felix to maintain him?

WT:  It’s almost $500 a month to board a horse, the medical, the shoes, the feed.  10 years, $500 a month, you can do the math but I don’t think he earned his own keep.

EG:  So the original owner, Charles “Bill” Frysinger, probably made a smart decision in unloading him for a $6,500 hit after 18 straight losses?

WT:  He got sold, sold again and then the last guy said, “I can’t make any money,” so I think they handed him off to the groom.  The groom’s name was Louis, I know his last name but I’m not using it because he was going to have him put down which would be illegal.  When Felix heard this, he screamed “No way, Jose.”

EG: Which leads into my next question.  After 20, losses he becomes property of “a vagabond” groom named Louis who then trades Zippy to Felix for an ’88 Ford truck with 188,000 miles on it.  That had to be a sign of what was to come?

WT:  Not a great omen, that’s for sure but they fell in together.  They were very much alike this horse and the trainer, hard headed, determined, never quit and always had hope.  He said to everyone that would listen, even to his wife that did not like the horse, “One day he’s going to be a winner.” Toward the end of his life he sure was.

EG:  I imagine the truck is not around anymore but Zippy still is.

WT:  Zippy is now the oldest horse at Old Friends Farm (a thoroughbred retirement centre in Cabin Creek, NY). 

EG:  He came close to winning against thoroughbreds a couple of times, the race against Black Rifle was contested by Zippy’s jockey, but Felix counter protested.  You gotta’ think that Felix kind of wanted the losing streak to continue, why would he support an outcome that went against his own jockey and horse?

WT:   Black Rifle (under the command of his garrulous jockey Frank Amonte, Sr., bumped Zippy several times over the course of the race) before leaning in and beating him by a nose.  Zippy’s jockey Juan Rohena immediately started screaming “Foul!” at the stewards, “I want an inquiry!”  Felix comes running out on the track and is grabbing him and says “I don’t want him to win this way on a technicality.”

I think at some point you’re right.  People Magazine in 2004 named Zippy as one of the 50 most intriguing personalities in all of America.  Now Felix is being asked for autographs, now he’s being asked to sign clippings and now treats are coming to the backside (stables).  I think that’s at the point where Felix said, “I’m not sure what’s going on here but I’m on to something. I’m going to keep running him.”

I don’t think they ever went out and slowed things down to make sure they lost.  I do think Felix, when he ran out on that track did not want Zippy to win on a technicality, with an asterisk beside his name.

They were honest, but got caught up a bit in the fame game.

EG:  Most casual fans know about the Triple Crown.  This book highlights lesser known tracks and local fairgrounds.  Is that non-commercial part of horse racing equivalent to the affinity people have for minor league baseball parks?

WT:  It is, it’s a lot like that and the whole thing is dying, I’d be surprised if Finger Lakes (Racetrack) is here a year from now.  You cannot convince people today, especially young people that five hours on a beautiful sunny afternoon at the track playing the ponies is a great experience.

EG:  What do you see in helping revitalize horse racing at that level?

WT: I don’t see it happening.  I see the bigger races getting bigger.  There will be less breeding of horses.  The big races are being seen because of California Chrome and American Pharoah.  This attracts the people that are not interested in horse racing (run on a lower scale).

EG:  Is there another Zippy Chippy in the making?  A horse out there that has lost anywhere close to something that can compare?

WT: I don’t think it will ever happen again.  The average horse only runs about six races.  Half the horses ever foaled for racing never get to race for one reason or another – they never make it to the track.

EG:  Should anyone be surprised that the term “sport of kings” was not used in this book?

WT: (Laughs) No, but in a related story I did say that with Zippy Chippy’s bloodline, it was like breeding King Juan Carlos of Spain with Princess Grace of Monaco and coming up with Prince Harry. It’s not an exact science.

EG:  Break down the following race involving Zippy and the following horses who lost over 100 races - Haru Urara, Thrust, Quixall Crossett, and Dona Chepa.

WT: My God, can you imagine that?  That would be a car wreck. I can only say that it might be the only horse race in history where (all) the horses tie for first.  I don’t see anybody winning that thing.

EG:  How long would it take?

WT: (Laughs) As one smartass at the track said, “Zippy’s biggest problem was not finishing in front of other horses, Zippy’s biggest problem was finishing before dark.”

EG:  It should be noted that Zippy won a few races.  He beat two non-thoroughbreds and he also is 2-1 against humans.  He lost to a human, how in the hell does that happen?

WT: That was my question to the jockey.  (In 2000) at 90 losses, Felix Monserrate says, “That’s it! We need a win some way, somehow.”

Dan Mason, the manager of the Rochester Red Wings “Triple A” baseball team, comes up with man against beast.  They set it up over 40 yards in the outfield (at Frontier Field).  Zippy Chippy against the fastest base stealer on the Rochester Red Wings – Jose Herrera.

Zippy had fans, 10,000 show up and the place is rocking.  Dan’s got the flag and the crowd starts chanting, “10-9-8…” (Jockey) Pedro Castillo is up on Zippy and when they get to about 3, Zippy started to eat grass.  When Mason yelled “Go!”  Zippy took that as a sign to eat faster and the player takes off.  Castillo hits him in the ass with the whip and the whole thing is over in 5 seconds.

EG:  This is the Eh Game so we need to talk about Zippy’s Canadian grandfather – Northern Dancer, safe to say the apple fell really far from the tree?

WT:  I think Zippy stepped on the apple and crushed it when it came down.

EG:  What would he think of his grandson?

WT:  He’d probably try and have the (lineage) charts burned.  Northern Dancer, the greatest stud ever and it just never worked with Zippy.

Just about every foal of Northern Dancer became a champion.  He just produced winners, except for one.

He would have come down and slapped Zippy around or tried to straighten him out somehow.

Northern Dancer would not be pleased.

EG:  Should Canadians appreciate Northern Dancer more than we do?

WT: I think so, he was the Wayne Gretzky of horse racing.  I think in the last Kentucky Derby something like 17 of 18 horses all had Northern Dancer’s DNA.  This is now, this is today, the horse stopped breeding in the 1960’s.

EG:  Anything else you want to add?

WT:  After Zippy came second twice in a row, Felix was so proud, he said, “My horse, he’s been losing real close lately.”  The first time I heard that I laughed and then I thought, life is so tough, none of us are American Pharoah.  We lose more battles than we win.  If you keep your nose clean, you keep your head down and try as hard as you can and leave it all out on the field, I think losing real close some days is plenty close enough.

Follow Neil Acharya on Twitter: @Neil_Acharya