The Riskiest Kentucky Derby Bet Of All Time

mark paul

The year was 1988. The month was January. The city was Los Angeles. The car was a Nissan 300ZX, the music inside the car came courtesy of Phil Collins, and the gamblers in the front seat went by the names Dino and Miami.

Their destination was Agua Caliente, a struggling horse track in Tijuana that was run by a powerful businessman, Jorge Hank Rhon, who came from a family described as “Mexico’s Rockefellers” and was rumored to be friendly with violent drug cartels. Only Dino and Miami didn’t know that at the time. They just knew that Agua Caliente was offering 50/1 Kentucky Derby futures odds on a filly named Winning Colors to win, whereas those odds were halved, if not quartered, at race books around the United States. 

(Grupo Caliente, the Mexican sports betting behemoth now owned by the 67-year-old Rhon, recently came quite close to being awarded a mobile license in the state of Illinois before its application was withdrawn, and Agua Caliente now hosts greyhound racing. The chain of tribal casinos in California that goes by the same name is completely unaffiliated.)

Dino, Miami, and a fellow horse betting enthusiast they called “Big Bernie” placed wagers at Aqua Caliente that would yield them $1 million if Winning Colors became just the third filly to beat the boys in the Kentucky Derby. With a pair of new love interests on their arms, Dino and Miami sweated out Winning Colors’ triumphant prep races at Santa Anita, and when they got the result they wanted at Churchill Downs on the first Saturday in May, their elation turned to dread as they plotted how best to collect their winnings from the Tijuana track they now feared.

Miami — real name: Mark Paul — wrote a book, The Greatest Gambling Story Ever Told, about this adventure. It’s sold well for a self-published tome and has attracted interest from Hollywood. The fact that Paul, now 66, is still alive is a spoiler of sorts, as it tells you that the worst-case scenario didn’t come to pass back in ’88.

Fresh off a trip to a gambling industry conference back east, Paul spoke to US Bets about his book and its potential cinematic adaptation last week. The Q&A below has been edited for clarity and brevity.

US Bets: Are you still in touch with Dino, Ava, or any of the other people in the book? 

MP: I’m still in touch with most everybody. Ava, which is not her real name (it’s Renee), I wound up marrying and she’s been my wife of 30 years. I’m still good friends with Dino. A lot of the people involved in the story are very afraid of the cartel. So am I. I’m just not smart enough to not write about it. The father of the racetrack owner, he was featured on Narcos: Mexico.

Have you been back to Agua Caliente since collecting your winnings?

I’ve been back once, maybe two decades ago. It was just some sports betting and I happened to get an opportunity to go, which I really shouldn’t have taken.

What level of confidence did you have that you would collect on your bet once you found out who owned Agua Caliente?

Most of my readers knew at the time they were reading it that Winning Colors probably wins the race. The reason I mention that is that the readers of the book are kind of aware that she’s gonna win. We were thinking, yeah, she had a real frigging chance, but we also knew that she was going to have to face 19 of the best male colts in the world, and a filly winning had only happened twice. We were scared to death and worried as hell, but we also knew she had to beat 19 other horses first. 

So it didn’t completely sink in until after she crossed the finish line first. We were worried that the track didn’t have enough money to pay. That was about the time that simulcasting first appeared, and it was a death knell for racing at Caliente. People used to go to Caliente because there was no horse racing in California on Sundays and the diehard gamblers would want to gamble on Sunday. But when simulcasting came in, you didn’t have to drive across the border — you could bet on races across the country, either from home or at track facilities.

I was actually more worried that they would pay us and then rob us — or just set us up. For a million dollars in Tijuana in 1988, it wouldn’t be that hard to just have a little roadblock the second you left the track or have a truck hit you.

How frequently do you bet on horses or other sports nowadays?

A lot. It’s so much easier nowadays. The NFL is the most exciting. I’m a big NBA guy, too. My larger wagers are still reserved for future-book betting — mostly NFL and NBA. I’m going to Vegas with my sons for the March Madness tournament.

Are your sons avid gamblers? 

They’re huge sports fans and my younger one, especially, really loves horse racing. They tell funny stories about what it was like growing up with me. If the Breeders’ Cup was in town, I’d get them up at 7 a.m. and say, “Get up. It’s time to gamble.”

While Santa Anita is featured quite a bit in the book, you also trace your gambling roots back to Hollywood Park. Does it bum you out to drive by the football stadium that took its place?

It makes me sad. I spent a tremendous amount of time there in my younger days. But I’m a bit of a realist. It doesn’t make any sense to have two ginormous facilities that can house 100,000 people in one city in today’s simulcast environment. I think that consolidation makes economic sense.

There’s a chance your book might get a cinematic adaptation. What are the odds of that happening?

The book has really been quite an amazing success. I sold about 45,000 books as a self-published author, which puts it in the top three-tenths of 1 percent of self-published books in America. I think the reason it’s been so well-received. If you get a country song that crosses over to the pop charts, it can really blow up. It’s very popular to gambling and horse racing fans, but a lot of women got very involved with a female racehorse trying to beat the boys in the Derby. A lot of women like horses and the idea of this beautiful filly beating the colts.

The book was also a crossover hit in true crime and white-collar crime. I’ve been on about 20 podcasts, but one of NPR’s top podcasts is a show called Snap Judgment, and the book is going to be featured on Snap Judgment. When I first released the book, it was optioned almost immediately by some well-known Hollywood people. However, with COVID it kind of fell apart. They wanted to renew it, but I didn’t like their terms, so I didn’t renew it.

I have an agent and my agent recently got another pretty well-known producer who had a script made for a potential movie. So I’m optimistic, but dealing with Hollywood people is not easy. They want total control and all the money. I kind of wrote it like a movie. I wanted to keep it short.

Don Johnson’s getting a little long in the tooth, so who would you want to portray young Mark Paul onscreen? 

A perfect analogy to my book, the right genre and the right kind of actors, was War Dogs. So maybe Miles Teller (as Mark) and Jonah Hill (as Dino). Racing could really use a good racing movie. The book has a happy ending. Almost all gambling stories are dark and brooding. The characters are drug addicts and drunks and nothing good ever happens in a gambling movie. 

A friend of mine at a golf club is a major Hollywood agent and producer. I gave him an early draft of my book and he said, “Mark, would you be OK if I give it to my readers?” Sure enough, I gave it to him and they came back with their 48 pages of recommendations and I was pissed off. But then I gave it to my wife and she said, “Yeah, they have some really good points here.” He told me, “If you want to tell a story of a couple of gamblers, keep the book the way it was. But if you make this book about Winning Colors, you’ll have a book that women will want to read and non-gamblers will want to read and have a chance to get it made into a movie.”

Did you have any interaction with Winning Colors’ famous trainer, D. Wayne Lukas? 

He really would not take interview requests. Gary Stevens, the horse’s jockey, was very open and gave me interviews.

You obviously got a great story out of wagering at a notorious racetrack, but if you had it to do all over again, would you have gone with a less exciting domestic operation? 

There’s a great quote: “An adventure is seldom enjoyable during the adventure.” And it really wasn’t up to me. If you knew Dino, Winning Colors, at the time we made the bet, was 12/1 in Las Vegas and was 50/1 in Mexico. If she had been 100/1 in the Brazilian rainforest, Dino would have been on an airplane to the Brazilian rainforest.

Photo courtesy of Mark Paul

Author: Ryan Gonzales