Kentucky Derby: 4 stories of ordinary bettors winning big

You don’t need to be a millionaire to win a big bet on the Kentucky Derby (G1). Play the right horse(s) in the right situation, and even a small budget can yield a lucrative payoff.

Since the turn of the century, several ordinary bettors have cashed six-figure and even seven-figure payoffs on Kentucky Derby bets. Their stories serve as reminders of why the Kentucky Derby is “the most exciting two minutes in sports.”

Here are the stories of four bettors who won big playing the Kentucky Derby:

Lost-and-found superfecta ticket yields record Derby payoff

When Giacomo rallied to win the 2005 Kentucky Derby at odds of 50-1, it was the second-biggest upset in Derby history. His closest pursuers—Closing Argument (72-1), Afleet Alex (9-2), and Don’t Get Mad (29-1)—helped trigger a record $1 superfecta payoff of $864,253.50.

Only seven bettors hit the superfecta, which required selecting the top four finishes in order. One was Christopher Hertzog of Phoenix, a longtime member of the Phoenix Fire Department. Hertzog bet 50 random $1 superfecta tickets at Turf Paradise, but after the Derby, he left his tickets at the track without realizing one was a winner.

Turf Paradise informed Hertzog of his winning wager, but by then, the physical tickets had been cleaned up. Hours were spent searching through garbage bags without success, but then the mutuel clerk who punched Hertzog’s tickets found two tickets on the floor. One was the winning superfecta, and Hertzog was able to celebrate his six-figure win after all.

$100,000 contest win bet pays off

In April 2010, CNBC offered a “Call the Close” contest in connection with Churchill Downs Inc. By guessing where the Dow Jones Industrial Average would close each day, winning players entered a random draw to win two tickets to the 2010 Kentucky Derby and a $100,000 win bet to place on the Derby horse of their choosing.

Glen Fullerton, a software designer from Houston, won the grand prize. Even though he wasn’t a horse racing expert, he had to choose which horse to bet on among 20 in the Kentucky Derby. He settled on 8-1 second choice Super Saver, partly because Super Saver would be ridden by Calvin Borel, who had won two of the last three Kentucky Derbys aboard Street Sense and Mine That Bird.

Fullerton’s handicapping paid off. Under a perfect ride from Borel, Super Saver won the Kentucky Derby by 2 1/2 lengths, and Fullerton—seen celebrating on the NBC television broadcast—cashed his ticket for $900,000.

$18 Pick 5 ticket pays $1.2 million

Making a million dollars betting on the Kentucky Derby favorite isn't easy. But in 2018, a woman from Austin, Texas, achieved the feat with a winning Pick 5 ticket on Kentucky Derby Day.

The Pick 5 ticket cost only $18, but it included non-favored winners in four races leading up to the Kentucky Derby: Limousine Liberal (4-1) in the Churchill Downs (G2), Maraud (8-1) in the American Turf (G2), Funny Duck (39-1) in the Pat Day Mile (G3), and Yoshida (9-1) in the Old Forester Turf Classic (G1).

The Pick 5 ended with the Kentucky Derby, in which 5-2 favorite and future Triple Crown winner Justify delivered on expectations with a 2 1/2-length victory. The Pick 5 paid $1,241,655.30 for a $1 base amount.

TwinSpires bettor cashes $741,019 Super High 5

The 2022 Kentucky Derby yielded one of the biggest surprises in history. Rich Strike started as the longest shot in the field at 80-1 odds, yet he rallied strongly from behind a blazing pace to win by three-quarters of a length.

Incredibly, one TwinSpires bettor from Ashland, Ky. managed to assemble a winning Super High 5 ticket, which required selecting the top five finishers in order. As detailed in the weeks following the race, the bettor boxed “a couple of longshots” with “a few frontunners” and managed to catch the winning combination.

Because the winnings were taxable, they weren’t deposited immediately into the bettor’s TwinSpires account, so a few days passed before the bettor realized their Super High 5 ticket had cashed to the tune of $741,018.90 on a $1 base amount.

Their success came just one day after hitting the $1 Super High 5 in the Kentucky Oaks (G1) for $7,511.30. “Really this past weekend was the first time I’ve ever played (a Super High 5),” the bettor told TwinSpires. “I normally play just a (superfecta) box or a (trifecta) box.”

With skill and luck, any bettor has the chance to cash a six- or seven-figure payoff in the Kentucky Derby. Want to join in on the action? Consider betting this year’s Kentucky Derby on TwinSpires.com, the official wagering partner of the Kentucky Derby. New players are eligible for a $200 signup bonus.