Behind the Book: Talking With Bill Doolittle About His Latest Project

Pop Culture

Photo by Eclipse Sportswire

Bill Doolittle is the author of the 1998 best-selling The Kentucky Derby, and The How to Be a Better Bettor Book. He has covered the Kentucky Derby for decades for publications like LEO Weekly and Lousiville Magazine. In addition to once being the on-track handicapper at Churchill Downs, Doolittle has also worked with the racetrack to chronicle their history as the writer/historian for the exhibit design team that created the Kentucky Derby Museum. He is the author and "project manager" for the recently published book The Kentucky Derby, a much more ambitious reboot of his 1998 coffee-table book. He spoke with David Hill about the book and his process.

Read part two of Doolittle’s interview tomorrow.

I'm really interested in racing history, and this book's got a lot of it. So, I was wondering if you could talk to me a little bit about your process in coming up with some of the stories and some of the history for the book. It seems like it's a combination of history that maybe we've read before, and there's some folklore in there too, and some stories that haven't been printed before, even.

Well I'm like you, I love all the historical stuff. Fortunately, what's great is that the Derby history - history is just a part of what makes the Derby what it is. Because it happens every year, and has for - you know, this'll be the 142nd running, and each one encompasses all that has come before, in addition to the lore and excitement of having one winner each year. You could say, "Well, I was born in 1980, and that was the year that Genuine Risk was the second filly to win it, and I was there ..." You have this feeling, all the time of honoring these old traditions, I like all that. 

When I was thinking about this book, I didn't want to make a chronological history. But I did want to find out what it was about the Kentucky Derby, how it got started and what made it stick as an institution. So those old stories are important to me, and a lot of them have been told and told, in books or different places. In time I think I kind of got it, got a grip on what it really was. And so, I think Churchill Downs wanted a really authoritative look at their beginnings. And I was happy to do that. As you can see in the book the pages have all those full color photos and stuff, but they also have full color stories. It doesn't matter if they happened this year or last year or a hundred years ago, they're just Kentucky Derby stories.

You said that you think you have a good handle on why the Derby stuck. What was it?

Well from the beginning, Meriwether Lewis Clark, he was called upon to do something to call attention to the Kentucky horse industry, like a sales promotion. And he dreamed up this idea of having the biggest horse race that (had) ever been. And it, well, it wasn't quite the biggest. There've been some attended more than this one - but it was huge. It was big and people loved it, and ordinary citizens loved it. So from the very beginning the Kentucky Derby was planned to be a great event, and they planned to do it every year in the springtime, which is our best time of the year. You know in Kentucky it's just perfect. The weather's perfect, the redbuds and the dogwoods and the grass is green, and all that.

And then a quarter century later, a fellow named Col. Matt Winn kind of found the Derby on the declining edge. And he took over the track and its Kentucky Derby and it just, you know, became a one-man movement. He just promoted the Derby constantly, day and night, all the time with all the big writers. He kept an apartment in New York City so he could visit with the writers on Broadway, Damon Runyon and all those guys. They would go to the big restaurants and Delmonico's - you know, that kind of thing. He was a promoter. But he also had to make the track profitable, and he is the person who first really utilized the parimutuel betting system. And it's an interesting story how that all happened. It was because gambling by bookmakers had been outlawed by law at Churchill Downs in Kentucky, and in a lot of places around the country. And Col. Winn just saw this new system of parimutuel betting. He saw it could make a profit for the track plus build a purse for the horsemen and most important, it would be fair for the bettors. He lowered the minimum bet from five dollars to two dollars. And that became the standard everywhere. So all these pioneering things happened. I wanted to document all that. 


I think the question persists in American sports about the Kentucky Derby. People all over the world are sort of baffled about how the Derby remains this massive spectacle and event even in a sport where other big races throughout the year don't get nearly as much attention. Yet here's this one race that get almost as many viewers as the Super Bowl. Where all of America stops for two minutes to watch it.  And I think it's a question that just perplexes everybody, about how the Kentucky Derby has thrived no matter what.  And just gets bigger and bigger.

You know it got big in the 1920s and ‘30s and early ‘40s with the Triple Crown winners and with the attention of writers. In the 1930s, the Associated Press covered the Derby and they used to use runners to go downtown and file the stories. Then they put a wire into the press box at Churchill Downs, and every year - the race was run at 4:30 in the afternoon then - and every year at 4:30 they would clear their A-wire. They had two worldwide wires, and the A-wire was the "breaking news," and they cleared it all the way around the world to flash the result of the Kentucky Derby. So that meant no matter where you were in any part of the world, you could hear what happened in the Kentucky Derby. Horses are long gone, nobody owns a horse anymore, but the people love horses, you know? What's more anachronistic than a horse race?

That's true. It's true, although it's only anachronistic now. Racing, as a sport, used to be more widely appreciated and was more a part of people's regional lives. And today, while a lot of that has diminished, the Derby has not diminished--in fact, it might be bigger now than ever while the rest of the sport has sort of vanished

I think you've got a very good handle on that, the idea that in the 19th century the horse did everything, racing was just a small part of it. Pull the ice wagon, took the country doctor around, and all those kinds of things. People rode them out west and herded cattle ... The horse was really something. And now, like we say, who's got one now?

I read the section about Kentucky, and horse farms, and how these people were breeding horses and selling them for use all over the country right up until the Civil War, and that racing was a small part of their business as breeders until some time much later when racing.

It's kind of like car racing. Racing is a small part of GM and Ford's business, but they go at it like crazy in the Daytona 500 or the Indianapolis 500. Racing is a glamour thing for a lot of them.

You also wrote a story in here about Sheikh Mohammed bin Rashid Al Maktoum coming to Keeneland and buying all the yearlings with a suitcase full of cash.

You think it's true?


I don't know, but it's a good example of what I was referring to before, about how this book has some great, not just history, but also folklore that I think is a part of horse racing in a way that it maybe isn't a part of any other sport. So much of this sport's history is kind of colorful folklore and stories that get passed around, and legends, maybe, for lack of a better word, and I appreciate it that this book has stories like that.

I wish it had more.

Can you tell me about how you collected those over the years, and your process as a historian?

Who wouldn't want to collect them? And then, of course, you get to be a storyteller, and it comes up Derby time, and you're at the bar, and the talk turns to Derby and you get to spin out another yarn. And as far as characters go, and scandal, things that would be a scandal in other lines of work are kind of grinned at, you know, around horse racing. As long as it doesn't get to be too far, a certain amount of chicanery is always ... You know, you’re kind of buyer beware when you go to the racetrack.

I imagine, in terms of being a historian of the sport, being in Kentucky probably helps a lot. You probably run across a lot of those kinds of stories just from being around the state and talking to folks who kind of lived through all of it, sort of an oral history of the sport.

Yes, you do. And I think it's true in other places, too. If you go to the race tracks in New York, Saratoga or Belmont, and hang around the stands. Or being in Florida in the winter, and everybody else is cold and you're down there with Derby races and the Fountain of Youth and the Florida Derby ... horse racing is a great participation sport. It really is. That's why places like Saratoga and Belmont and Keeneland, people get dressed up to go to the track, and they just like it. You can take a date! 

Be sure to pick up your copy of Bill Doolittle's “The Kentucky Derby”

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