Rico Flores and fiance Denise Crane

Rico Flores and fiance Denise Crane

Esther Marr

Chicago Resident Wins $100,000 Bet in Derby

Rico Flores won the $100,000 Derby Dream Bet Sweepstakes.

Chicago resident Rico Flores has won a chance to place a life-changing $100,000 bet in the May 7 Kentucky Derby Presented by Yum! Brands (gr. I).

By entering an online contest, Flores was randomly drawn to place the free wager in conjunction with the $100,000 Derby Dream Bet Sweepstakes, which was offered for the second consecutive year due to a partnership between Churchill Downs and NBC Sports.

A year ago, Glen Fullerton of Houston, Texas won $900,000 when Super Saver  won the Kentucky Derby at odds of 8-1.

Flores said he “never misses” the Kentucky Derby and estimated he’s attended the race at least 20 times. This year, he’ll have a VIP trip for two to the Kentucky Derby and Kentucky Oaks (includes airfare, lodging, and ground transportation) and the chance to place a $100,000 win bet on any horse in the Kentucky Derby.

If the horse wins, Flores will keep the winnings, just as Fullerton did a year ago.

Flores, who met his fiancé, Louisville resident Denise Crane, at the Kentucky Oaks (gr. I) four years ago runs two manufacturing companies in Chicago. When notified about winning the opportunity to place the $100,000 Derby Dream Bet, he thought it was a prank.

“They called about five times and I didn’t answer because it said ‘restricted,’ ” said Flores, adding that he didn’t even remember entering the contest. “At about 6:30 p.m. they called again and I told my niece, “I’m going to give these people an earful to quit bugging me.

“The woman on the phone said, ‘This is Pam with NBC Sports,’ and I said, ‘Yeah, right.’ And she said, “Don’t hang up—you’re the big winner!’ It’s lucky I answered on the sixth try, because at 7 p.m. they would have called another person’s name.”

Flores said he had not yet decided on which horse he would place his $100,000 bet. “I (handicap) by trainer, past performances, pedigree, jockey, weather positions, post, etc. A lot plays into it,” he said, adding that he had his top five horses in mind and that he would factor the weather into his pick on Derby Day. 

Flores, who typically travels to Churchill for the Derby each year with a group of 10 friends, has also been attending the races for around 20 years at the Chicago-based Arlington Park. “Maybe one day I’ll hit my retirement fund; maybe Saturday is the day,” he said with a laugh, adding that the most he had won thus far betting on a race was around $30,000.

Derby Day may just be the perfect opportunity for Flores to greatly exceed his personal best, but the decision won’t be easy considering this year’s wide-open field. “There’s a lot of factors that go into racing, and it’s just anybody’s guess—especially this one,” he said.

Added Crane: “I don’t think he’ll know (who he’s going to bet) until he goes up to the window.”