On a November afternoon this past winter, a man in his 30s walked into The SuperBook at the Westgate Las Vegas and wanted to place bets on two college basketball teams to win the 2019 title. One wager was on Wisconsin at 100-1 odds, and the other was on Texas Tech, a team that had opened at 40-1 back in April, but whose odds had plummeted to 200-1.
The bettor (who didn't wish to be identified for this story) wanted more than $1,500 on Texas Tech, but SuperBook director John Murray declined. "He's a well-known player who takes a lot of futures positions with us," Murray told ESPN. "He asked for more, to which we said, 'No.' I think to win $300K is pretty good."
The bettor settled for a $1,500 ticket on the Red Raiders at 200-1 odds, for a payout of $300,000.
Almost four months later, that ticket was one game away from cashing. And despite an offer from Dez Bryant and another for $125,000 on PropSwap (a secondary marketplace for sports-betting futures tickets), the bettor let it ride. Texas Tech lost to Virginia 85-77 on Monday night in the championship game.
He made other college basketball bets, including several on Virginia winning, so he still won some money. But he'll always be contemplating what could have been if Texas Tech had won.
The bettor told ESPN that sports betting is a hobby of his -- not his full-time job -- and he began around eight years ago.
"It's something that I do for fun," he noted. "I live on the West Coast, so it's somewhat convenient for me to get to Vegas. College basketball is the sport I enjoy watching most, and my interest in betting stemmed from a love of watching sports."
He likes making futures bets on college basketball because of the large variety of teams and long odds available rather than individual games, and he usually makes several trips to Vegas throughout the season to get money down. On long-shot futures: "It's kind of like buying a lottery ticket or a big parlay, but something that I think has a more reasonable chance of winning."
In addition to the $1,500 futures wager on Texas Tech at 200-1, ESPN learned that he also had a $1,500 ticket on Michigan State at 40-1 and an $800 wager on Texas Tech at 125-1 odds (for a potential payout of $100,000). In addition, he had a smaller futures position on Virginia.
"I liked the long odds on Texas Tech at 200-1," the bettor said. "I had bets on them last year at 250-1, and even though they fell short in the Elite Eight, they returned a lot of the same guys and the same coach."
After losing out on all of his long shots last year without hedging (including Clemson at 500-1), the idea of selling a futures bet in a secondary marketplace like PropSwap was very appealing.
"I wasn't aware of PropSwap [before]," he told ESPN. "But it's cool that I can get some money back from these tickets and someone has a chance to win big."
He said $1,500 was "pretty close to his ceiling" in terms of futures bets, which makes the question of hedging all the more interesting. Why not hedge more on such a valuable Texas Tech ticket?
"The way I think about it is, if I hedged they probably wouldn't have won," he told ESPN on Friday. "Say Texas Tech beats Michigan State but Jarrett Culver gets hurt. Then all of your assumptions about Texas Tech and how much you should hedge now and in the final game goes out the window. It's much nicer to take the fixed amount and not have the hassle of thinking about anything else.
"People make hedging sound easier than it is, both in having money lying around [and how to] bet on this stuff. You can easily make a mistake, and then it might not pan out the way you think it might."
For a few hours on Friday afternoon, Bryant had the high bid of $50,000 on PropSwap for the $1,500 Texas Tech ticket (the bettor was asking for $65,000), and the highest official bid came in at $57,500. The bettor declined both bids and let the bet ride into Saturday night's Final Four game against Michigan State.
He did sell his $800 Texas Tech ticket for $20,250 on PropSwap on Saturday morning, hours before the Red Raiders defeated Michigan State 61-51 to advance to Monday night's title game.
He put his $1,500 Texas Tech ticket back up on PropSwap on Sunday but would've needed an astronomical bid to sell. He declined a $125,000 bid.
Lest anyone think he's solely motivated by financial gain, the bettor also has given away several futures bets as -- get this -- wedding and birthday gifts.
"One thing I started doing in the past few years is giving tickets to friends as presents," the bettor recalled. "It could be a birthday present, but my favorite is the wedding present. I think it's a nice thing. They can choose to let a bit of it ride, all of it ride, none of it ride. It's kind of cool to see different people's risk tolerances. It's a good conversation for a couple to have."
And they're not all long shots that don't have a chance to win. Last year, he made one friend some real cash.
"Yeah, I did give Villanova at 6-1 as a birthday present last year," he said with a chuckle. "The couple didn't hedge and Villanova won, which is really cool for them. I'm obviously really happy about it."
It's clear the bettor has a large bankroll and there is a method to his futures betting madness, even though he says he doesn't have a formula determining how much to bet on each team.
"I haven't been in a similar situation before," he joked before Monday night's game. "But I'm obviously happy to be in it."
He may be thinking twice about not hedging, despite the money from his other futures tickets.