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We love zero to hero stories — especially in the world of sports betting. They are rare, but they do in fact happen. But this story is one of our favorites.
The Athletic (which is owned by the New York Times) reported the story of “Thousands Dolla Bill” — a pseudonym for a bettor. While his real name is unknown, he described himself as a 45-year-old Floridian from St. Augustine.
Bill, as we’ll call him the rest of this article, graduated from the University of Florida. And there lies the dilemma. He was one win away from turning a $5 parlay into a $168,000 win. The issue? He was on the other side of Florida — needing Duke to win in the March Madness tourney (both teams were favorites as No. 1 seeds).
By now, you know how the tourney ended. Duke choked in the Final Four against Houston, and Florida eventually beat them in the NCAA title game in a nail-biter. Does that mean Bill came up empty? Not quite. Keep on reading for his full story!
Bill Throws Hail Mary Bets
When sports betting in Florida became a thing, Bill began dabbling in it. As you may or may not know, the Sunshine State has a unique legal sports betting market. The only betting app allowed is Hard Rock Bet due to a compact the Seminole Tribe (who own the brand) has with the state.
Bill took his talents to Hard Rock Bet, which began accepting bets in 2024. His first order of business? Throw up some parlays, particularly on title winners across different sports.
“I thought it looked kinda cool, and I threw in like 10ish of these parlays [on Hard Rock Bet],” he 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.”
On May 12, 2024, Bill placed a $5 five-leg parlay. The first four legs? Tennessee winning the College World Series (+650), the Los Angeles Dodgers clinching the World Series (+300), Ohio State taking the College Football Playoff (+450), and the Philadelphia Eagles securing the Super Bowl (+1600). All winners hit by the time March Madness rolled around, leaving Duke winning the NCAA Tournament (+1100) as the final leg.
The odds of this parlay hitting when Bill first mustered it? A jaw-dropping +3,365,900, or 33,659-to-1. Hard Rock Bet confirmed that this would be the longest odds of any bet cashed at the sportsbook in 2025, hence the potential $168,300 payout off a measly $5 staked.
Duke Puts The Pressure On Bill
The Blue Devils are always national title contenders, but especially this year due to Cooper Flagg — the consensus No. 1 pick in the upcoming NBA Draft. Flagg and the team lived up to the hype all year en route to a No. 1 seed in the tourney. But as they kept winning, the pressure started to pile up on Bill.
With the stakes high, Bill looked for a cash-out feature. Most apps offer this to bettors who want to settle their bet early — for a reduced price, of course. Only, the option was nowhere to be found.
“I didn’t have a cash-out offer from Hard Rock when Duke played [Mount St. Mary’s] in the first round. 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.”
Hard Rock Bet explained that a system change after Bill placed his bet led to older wagers not receiving cash-out options. Eventually, before the Sweet 16, Bill received a cash-out offer and began exploring hedging strategies.
This led Bill to PropSwap, a platform for buying and selling active sports bets. He ended up getting a direct line to PropSwap’s CEO, Luke Pergande, who explained what the market value of Bill’s parlay even was. Right before Duke’s Elite Eight matchup — and three wins away from a national title — the ticket was worth $40,500.
Bill sold half the parlay (yes, you can sell fractions of a ticket) right then and there.
Duke won that matchup before its epic collapse the weekend after against Houston. So in the end, Bill made the right move as he would’ve been zeroed out if he kept it.
Gators Played A Role In The Decision
Nevermind just the life-changing money that was at stake. Also factoring into the early-sell decision was Bill’s allegiance to his own alma matter, who were still dancing alongside Duke. Asked by The Athletic about a potential Duke-Florida finale — which was wildly predicted at the time — Bill had a simple reply.
“Root for the good guys,” with the good guys being his favorite team — not the one that could’ve made him big cash.
The article was written before Florida wound up cutting down the nets, but surely, Bill was a happy man, as he co-celebrated a $20,250 come-up from selling his ticket early and a national title from his favorite team.
It’s worth noting that the article mentioned another parlay Bill was still tracking for: a $6.34, four-leg championship parlay. It too included Ohio State and the Eagles. The remaining legs were Duke and Oklahoma City Thunder taking the NBA championship. It had $52,164.89 on the line.
Did Bill cash that one out early? No, per the article, Bill wanted to let it ride. Welp, he rode that to zero given the Blue Devil’s crash out. But hey, you can’t win ’em all!
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