Over the past decade, the Tribune, like many media outlets big and small, has hemorrhaged jobs. This summer, in the midst of the coronavirus pandemic, there were furloughs, casting its future in ever shakier terms. Greenstein headed for what looked like greener pastures, pegging his career squarely on the future of legal sports gambling.
Since the Supreme Court overturned a federal law in 2018 that limited sports gambling mostly to Nevada, 19 state legislatures and the District have legalized sports gambling in some form, with another 27 moving toward legalization. The early returns have been encouraging. In October, for instance, the amount of money bet in New Jersey eclipsed $800 million, more than the $650 million in Nevada.
In a rush to attract these new customers, gambling operators have turned to sports media companies, which are in their own race to cash in on the legal-betting boom. ESPN, NBC and CBS have formed lucrative advertising partnerships with big-name sportsbooks. Fox Sports launched its own gambling company, FoxBet. Barstool’s owners sold a large stake to a betting company. Last month, Sinclair bought a stake in gaming company Bally’s and said it will rebrand its 21 regional sports networks using the Bally’s name.
Sinclair CEO Chris Ripley said in a recent interview that gambling will transform a sports industry that is reeling from the pandemic, watching advertising and cable bundle fees shrink. “It’s a third revenue stream to maintain the growth of the industry,” Ripley said.
Greenstein’s move represents one aspect of that transformation: a gambling company positioning itself as its own media company and leveraging the following and expertise of a well-known sportswriter in that effort. It’s likely to happen more as legacy and sports media brands struggle. In the days after his announcement, Greenstein said he heard from around a dozen colleagues around the industry, asking some form of the same question: “Are you hiring?”
Other gambling companies have poached talent from the ranks of sports media in recent years. BetMGM hired Ryan Spoon, ESPN’s head of digital content, where he oversaw things such as ESPN’s app and the expansion of “SportsCenter” into Snapchat. PointsBet has another executive, Len Mead, who used to lead programming at NBC Sports Boston and NBC Sports Northwest.
“We’re all media companies,” said Yaniv Sherman, the head of business development at another gambling company, 888 Holdings. “We’ve realized we need to be producing content.”
Greenstein, in his early days at PointsBet, is not covering sports like a traditional sports reporter. He is making football picks every weekend and producing videos about best bets for events such as the Masters. He’s also producing tutorials for prospective customers about how to bet. The focus is to both educate prospective customers and keep them on the PointsBet site and app longer.
Sports reporters have always been crucial to the gambling industry. Brian Musburger, CEO of Vegas Stats & Information Network, recalled stories from the 1970s and ’80s, when Vegas sharps camped out at McCarran Airport waiting for newspapers to be delivered from around the country each day. Inside were news of injuries, depth charts and other nuggets that could give them an advantage vs. the house.
“There is a long history of guys looking for an edge,” said Musburger, who in 2017 hired his famous uncle, Brent, to host a radio show. “It’s harder to have that now because information happens so fast. But guys like Teddy, who have their ear to the ground and have covered a beat, whether they know it or not, they have information that is important to sports bettors.”
In an uncertain media landscape, gambling companies have lots of advertising dollars to spend. DraftKings spent more than $200 million on advertising just in the third quarter of 2020. If these companies are looking to keep customers engaged, a team of journalists to provide their platform with market-differentiating reporting could make sense. Could a gambling company employ its own Dallas Cowboys beat writer, for instance, if that reporter has insights into the team?
“The places that have the money to hire the best writers right now are the folks that are serving the gambling audience,” Brian Musburger said. “So it’s interesting.”
Yet he wondered about the optics and risks of having a reporter working for a sportsbook in the locker room. One question it would raise: Would that reporting go first to the oddsmakers setting the lines or the customers trying to beat them? “I don’t think the leagues will go for it,” he said.
But what if they’re not in the locker room? A reporter who specializes in breaking national transaction and injury news — an Adam Schefter in football or Adrian Wojnarowski in basketball — could offer up-to-the-minute information for one book’s customers. Wojnarowski or Schefter could break news not on ESPN or Twitter but in a gambling app.
Chad Millman, a former editor in chief of ESPN the Magazine who is now head of media at the Action Network, a gambling-focused media company, thought those kinds of scoops wouldn’t be that valuable to a sportsbook because so many outlets confirm or aggregate breaking news nearly in real time. But, he said, adding a personality with the huge Twitter following of one of those star reporters could be worthwhile as part of a company’s quest for visibility. It also could be a better investment than paying to slap a company’s name on a team’s stadium or website. (Action and VSiN have their own business models, collecting subscription fees and also referral fees when they send customers to sportsbooks.)
Greenstein and other splashy hires aside, some gambling experts are skeptical that professional sportswriters will do much to drive betting’s expansion in the United States. Ultimately, the functionality of a company’s app and seamlessness of the technology to make bets could trump written reporting, especially as bettors move toward in-game betting, which dominates wagering in the more mature markets of Europe. Aubrey Levy of the Score, a Canadian-based sports media and gambling company, said, “Our opinion is we can do a lot more with product than with big-name hires.”
And, of course, any bettor can still shop around for better lines and odds across the marketplace regardless of who is keeping them most informed.
Sherman said 888 spends some $200 million each year on marketing and that he would prefer to partner with a media company rather than build one. “Gaming operators aren’t news desks,” he said. “That reporter needs to report to someone. You need an editor.”
He said he expected more partnerships to emerge, including, specifically, some gambling company to strike a partnership with the Athletic, the venture-backed subscription sports media company that boasts more than a million subscribers. In March, the Athletic told The Washington Post it had no plans to pursue gambling content or partnerships. A spokeswoman said this week that the company is evaluating its long-term betting strategy.
As for whether sports gambling would ultimately save or swallow sports media, Millman questioned the premise.
“Why does it have to be one or the other?” he asked. “Can’t it be both?”