U Bracket Hinge

Wayne Shelton walked into Paycom Center on Tuesday for his first ever NBA playoff game. It was Game 1 of the Western Conference semifinals between the Dallas Mavericks and the Oklahoma City Thunder.

Shelton, a single father of one and owner of a real estate appraisal business in Phoenix, Arizona, is "nervous as hell." Over the past year, he's become one of the Thunder's biggest supporters -- not for sentimental reasons, but because the team may help him cash the parlay of a lifetime.

Shelton avidly watches and bets on sports, often using multiple screens to keep up with all of the action. However, his method for sports betting isn't exactly conventional: He largely only bets futures, very rarely dabbling in day-to-day betting.

"I plant seeds throughout the year," Shelton told ESPN. "I bet all the major sports for all the futures, divisions, whatever. And the whole idea is I'll invest a decent amount, but now I get to enjoy the entire season as a sports bettor without having to put more money down. I can enjoy what I invested and enjoy every game because they all matter."

So over one year ago, May 1, 2023, when DraftKings offered him a high-limit, 50% profit boost, he knew he had to take a shot.

Shelton noticed that the Texas Rangers had an outrageously positive run differential a month into the MLB season and, on that day, believed they were a better shot to win the World Series than their 22-1 odds suggested. He began his process of "research" -- but for the purposes of this new bet, that term will be used loosely. A family member whose family was "not really into sports" started following the Kansas City Chiefs, so Shelton felt betting a repeat for the reigning champs could be fun at +600.

Then there was the Thunder, who Shelton believed showed potential after a feisty outing as the 10-seed in the play-in tournament. At 70-1 to win in 2024, OKC was the final piece of Shelton's puzzle.

He packaged the three championship futures into a $100 parlay to build a new futures ticket. The payout: $1.7 million.

"I never bet that high on a future, especially a lottery ticket like this one," Shelton said. "They gave me a high max and I just said, 'You know what? This one time, max it out, let's go.' [I] never do that. [And] here we are."

In November, the Rangers won their first World Series in franchise history. In February, the Chiefs repeated as Super Bowl champions. Now, the Thunder, the Western Conference's No. 1 seed, are three series wins away from capturing the franchise's first NBA title since moving to Oklahoma City.

"Most people would prefer to [bet] day-to-day, and that's because you get your payout immediately," Shelton said. "For someone that does it like me, you have to be willing to invest. You have to know you are not going to get paid tomorrow. It's been a year since I made the ticket and I've just enjoyed the ride."

Shelton aims to have 40 futures tickets active at any given time, so he's generally familiar with the options available to him to maximize his profit. However, with so much money on the line this time (his previous biggest win was $7,000), he has had to think about it a little harder.

The most traditional method is hedging, which he did ahead of the Dallas-Oklahoma City series to the tune of a $10,000 payout should the Mavericks win. He said he will "probably" hedge each round if the Thunder continue to win.

Additionally, like all major sportsbooks, DraftKings offered a cash out on the wager, but at around $75,000 following OKC's opening round series win, Shelton didn't believe the value aligned and started looking at his options to cash out elsewhere.

After the Super Bowl, reports emerged of a betting ticket that was just a Thunder title win away from cashing $1.7 million. Travis Geiger's ears instantly perked up.

About four years prior, Geiger, Zach Doctor and Guy Dotan, all alumni of UCLA, founded WagerWire, a secondary betting ticket exchange born out of the founders' desires for a place to buy into each other's action. While the company isn't the first of its kind -- PropSwap, for example, launched in 2015 -- Geiger and his co-founders believe they got in early on something that could become a staple of the betting industry.

"This is not only a way for you to ride with your friends, but a way for you to play it like an asset that you're more familiar with, like a pair of sneakers, like crypto, like a stock," Geiger told ESPN. "It takes what was a risk class and makes it an asset class. If you game it all the way out, it creates a secondary market, and, as we know, secondary markets are kind of an inevitability of capitalism."

Users sync their sportsbook accounts with WagerWire, populating their wagers in the app's system. From there, they can shop their bet around to other users or wait for offers to come in. They can, of course, purchase other users' wagers as well.

The app's bet value calculator tells users how much a given ticket is worth based on the original odds/payout and the probability of it cashing based on events that have already occurred. In Shelton's case, WagerWire valued the ticket at just over $180,000 ahead of the Thunder's series against the Mavericks.

Geiger wanted the opportunity to land this ticket on WagerWire, as it would be the biggest bet the platform ever handled. He reached out to the purported ticket holder -- only it wasn't Shelton, but instead a 23-year-old named Sean Koehler, who attempted to co-opt the internet fame by claiming the ticket was his.

Shelton caught wind of the scheme and contacted Koehler, who admitted to duping media outlets. Shelton eventually verified the bet was his by syncing his DraftKings account in WagerWire. DraftKings declined to comment for this story but confirmed the legitimacy of the ticket.

Though Shelton wasn't sure if he even wanted to sell, he listed the ticket on the platform to keep all his options open.

Right now, WagerWire makes its money by splitting "nominal" buyer transaction fees with sportsbooks, which vary from operator to operator. For big transactions like Shelton's -- as well as that of Martwon Weaver, who sold a $680,960 NFL awards parlay that ultimately lost for $25,000 -- the company waives its fees.

The sportsbooks handle all of the actual transferring of wagers -- a feature that keeps the secondary market compliant with betting laws.

"The PropSwap transaction relates to what the holder of the sportsbook ticket wants to do with that piece of paper, which is now really a contract, between the player and the book," Nevada attorney Dan Reaser told ESPN about PropSwap in 2017. "It is not the business of taking wagers to facilitate someone buying or selling that contract."

Geiger feels that his company's product complements sportsbook's cash-out options, which are inherently lower than market value to align with their own business needs. To that end, it's possible that WagerWire and similar products could eventually directly integrate with sportsbook interfaces, providing a more appealing alternative right in the apps.

It might eventually look similar to the secondary events ticket marketplace: If a user couldn't get the ticket they wanted at the original price, they can pay a premium to get in later.

Finding a buyer willing to pay thousands -- or hundreds of thousands, in Shelton's case -- to get in on the action can be difficult. This is where another company, White Glove Bets, enters the picture.

Self-described as a "concierge service" for digital betting, White Glove Bets has a stable of "high-level VIPs" that ordinarily cannot deposit money at major sportsbooks due to the inherent risk they bring with their deep coffers. While they're not what you would call professional bettors, these players regularly make six-figure deposits and wagers.

"They have that Type A personality, if you will," White Glove Bets co-founder Kevin Smith told ESPN. "Many of them are business owners or at least executives that are pretty high up the food chain." He added that many of the company's clients also work in the financial sector. Smith said the clientele is "predominantly" male bettors with some as young as 25 years old. Several have been circling Shelton's ticket.

One of the potential investors, who has a particular penchant for futures, was very intrigued by the final leg of the wager and expressed interest in buying it. Smith has requested that the potential buyer remain anonymous.

White Glove Bets set them up with WagerWire, who facilitated a $100,000 offer to Shelton -- who promptly turned it down.

At that time, Shelton characterized it as a fair offer given DraftKings' cash out was approximately $55,000. But knowing that the Thunder were likely to knock out the Pelicans in the first round of the playoffs, he decided to hold onto the ticket, anticipating a value increase. He also had some reservations about the still emerging secondary market.

"The first thing that was going through my head was, 'Wow, ok somebody is considering a hundred grand,'" said Shelton. "If somebody's willing to offer me a reasonable amount above cash out, I'm not going to ignore it, no question. It's just that I have to trust the company that I'm talking to or the person I'm talking to, and I just don't know these companies well enough to be comfortable saying, 'Sure, I'll do that.'"

Since then, Shelton claims to have gotten several offers over $100,000, though he notes that many of these, including one for $200,000, were not legitimate. Protecting the original ticket remains his top priority.

Still, if the secondary market can continue to grow and be taken seriously, it could provide the alternative to cash outs that high-end bettors have been waiting for: Only a "super VIP" could have the capital to bail Shelton's ticket out above the cash out value, and such a buyer could also have the means to properly hedge the bet all the way.

"As [the big betting operators] become more corporate, they have less tolerance for high-end VIPs," Smith said. "I'm not being critical of them at all or their business model."

While the financial thrillseekers wait in the wings, looking for that moment to make him a life-changing offer, Shelton is just enjoying the ride. He says he might take a vacation and wants to meet someone famous if and when he comes away with the money, but hasn't put a lot of thought into it because it isn't tangible. For now, the betting everyman is staying the course, taking his monumental decision day by day.

"My family has been supportive, people online -- and there's a lot of them -- have been very supportive, and that does help with the immense amount of stress that comes with this," Shelton said. "And when I say stress -- find like 30 different emotions, bundle them up together, and it's that way all the time. But I appreciate that and I appreciate that people haven't been harsh and cruel."

On Tuesday night, with Shelton in attendance, the Thunder won the first game of their series. The new value of the ticket, according to WagerWire, is $228,613

"[I'm] relieved that I get a day to breathe," Shelton told ESPN Wednesday morning. "Awesome game and environment."

This was the only game of the series Shelton was planning on attending. Now it's back to Arizona where the largest sweat of his life -- and perhaps others -- will continue.