Wingo told me, “At the end of the day, once the Supreme Court ruling happened, the N.F.L. was really good at three things. One, they put out a product you just can’t get enough of. Two, they know how to market the hell out of it. Three, they know how to make money. And once this thing came open, they knew that there was money to be made. And the NFL is a moneymaking machine.”
Wingo himself recently joined Caesars Sportsbook as chief trends officer and brand ambassador. He told me that he sees his job as having changed little from his work with ESPN. He’s still the “why” guy, explaining to an audience on his podcast and on YouTube how a player’s stats and performance might influence how they do on any given Sunday (or Thursday or Monday). But with respect to gambling, he said: “We can talk about it now. It’s a little more open.”
A historical aside: Gambling was part of the N.F.L. at its inception. It’s rumored that the Steelers founder Art Rooney kept the team afloat through the 1930s with gambling winnings, and the Giants founder Tim Mara was a successful bookmaker. Even basic aspects of the game’s operations — like the weekly injury report teams are required to submit to the league — are arguably done for the benefit of Vegas casinos looking to set the lines and determine which teams they think will win and by how much.
But despite the game’s betting origins, gambling on the N.F.L., if it took place at all, was heavily discouraged by the league, meaning that it was largely kept an open secret, an activity only for mobsters and the very sad.
Some with close ties to the league aren’t happy about the changes in recent years. In a conference call with reporters, the former Indianapolis Colts head coach Tony Dungy said that he didn’t support the N.F.L.’s new stance on betting. “I don’t think we should encourage people who are watching the N.F.L. to gamble, especially young people,” he said. “I’ve got boys, and I want them to enjoy the game for what it is, the headiness of it and those kinds of things.”
There are two main concerns about legalized sports betting and the N.F.L.: first, that the game itself could be corrupted if players, coaches or referees “fix” games to help gamblers, and second, that users may risk developing gambling addictions with the prevalence of so many options for betting.
Wingo told me that he hoped that legalized sports betting would actually help stop players (or coaches) from intentionally trying to score fewer points or lose games. He gave me the example of a 2007 tennis match held in Europe, where in-game betting is far more common than it is in the United States. After noticing suspicious activity — namely, a lot of money coming in favoring a player who was already losing — the sports book Betfair halted all transactions and notified the A.T.P. of its concerns.