For many sports bettors, one of the toughest decisions is betting with your heart versus betting with your head. Do you blindly back your favorite teams that you’ve been a diehard fan of for your entire life? Or do you opt for a different squad based on what the numbers say?
Thousand Dolla Bill — who asked to be referred to by his college rapper nickname for this story — is a 45-year-old who resides in St. Augustine, Florida. He was born in Jacksonville and has lived in Florida his entire life. That includes attending and graduating from the University of Florida, following in the footsteps of his mother, father and brothers.
Hard Rock Bet is the only legal sportsbook that operates in the state of Florida, and “Bill” started placing sports bets there once the app launched. In terms of his betting style, he likes to mix straight bets and parlays. One day, he saw a championship parlay on social media that piqued his interest.
“I thought it looked kinda cool, and I threw in like 10ish of these parlays [on Hard Rock Bet],” Bill told The Athletic. “After I did it, I just kind of forgot about them. I just put a couple of bucks on each and hoped for the best. Two of them are still going.”
Betting on parlays like these is akin to buying a lottery ticket, where your chances of winning are extremely slim and the odds are very long.
The first wager Bill placed was a $5, five-leg parlay on May 12, 2024, where the first four have all cashed — Tennessee to win the College World Series (+650), the Los Angeles Dodgers to win the World Series (+300), Ohio State to win the College Football Playoff (+450) and the Philadelphia Eagles to win the Super Bowl (+1600). The final leg separating Bill from a $168,300 payout is Duke winning the college basketball national championship (+1100).
If you were curious about the odds on that parlay, it’s +3365900 or 33,659-to-1. And, yes, that is his ticket above. Hard Rock Bet confirmed that if Duke wins the national title, that parlay would have the longest odds of any bet cashed at the sportsbook in 2025.
“I didn’t have a cash-out offer from Hard Rock when Duke played [Mount St. Mary’s] in the first round,” Bill said. “When they played Baylor in the next round, I didn’t get an offer either. That Sunday was a little stressful because I basically had $168,000 on Duke and didn’t have another option. Some people’s nerves aren’t built for what was going on, and I guess mine weren’t really either. I couldn’t sleep for a little while.”
A representative from Hard Rock Bet told The Athletic that it had changed systems after that parlay was placed, leading to older wagers not receiving a cash-out option. Bill first got a cash-out offer on his parlay from Hard Rock Bet the Monday before the Sweet 16, and that is when he started exploring hedging opportunities.
He had not posted from his X account since he created it (when it was Twitter) in November 2010, but started using it after he took a photo of his bet ticket and tagged several accounts in the industry, including first mentioning Hard Rock Bet on March 24 about getting a cash-out offer from the sportsbook. That’s also how he found PropSwap, a secondary marketplace for buying and selling sports bets.
“I got in touch with [PropSwap’s] CEO Luke Pergande, who really helped me through this thing,” Bill said. “I didn’t know what the fair market value for something like this might be. So I had to get an appraised value for this parlay. I ended up taking approximately half an offer after taxes that I was getting back from Hard Rock, and I kept half the bet going.”
Bill sold 50 percent of his parlay for $20,250 on PropSwap on March 29, ahead of Duke’s Elite Eight battle against Alabama. After getting something for his parlay instead of potentially walking away with nothing, Bill also wanted to set himself up to hedge out of the other half of his parlay if Duke ends up facing his alma mater, Florida, in the national championship game. Why? So he can “root for the good guys.”
Since there wasn’t a professional Florida basketball team nearby in his early childhood years, Bill is a massive supporter of University of Florida football and basketball, the Jacksonville Jaguars and the New York Knicks. The Gators will always be his top team, though. Bill was willing to include rival Tennessee in his championship parlay because he doesn’t follow college baseball as closely, and he thought the odds were attractive for the No. 1 seed in the College World Series. Conversely, he says he would never include Tennessee for football or basketball.
His other notable bet that he still has riding is a $6.34, four-leg championship parlay, with Ohio State and Eagles legs already cashed. Duke to win the NCAA Tournament is the third leg, and the final part is the Oklahoma City Thunder securing the NBA championship (+750). That parlay has odds of +747900 and would pay out $52,164.89. Bill says he has zero interest in taking a cash-out offer for that parlay and is letting it ride. For what it’s worth, the Thunder are currently the favorites to win the NBA title at BetMGM at +175.
What about including his favorite teams on these types of parlays going forward? He’s checked that box, too, as he currently has a Florida college basketball title and Knicks NBA championship parlay riding for four figures. He’s also trying to find a way to include Florida quarterback DJ Lagway to win the Heisman in a parlay. But there are always exceptions.
“I would never put the Jaguars in anything in my life.”
(Photo of Cooper Flagg: Elsa / Getty Images)
