On an August 8 earnings call, Penn Entertain CEO Jay Snowden laid down a marker. “We will maintain our disciplined approach to customer engagement when we launch ESPN BET in New York in late August,” he said, noting that key upgrades would be made and regulatory green lights would be given “prior to the start of college football and our launch in New York.” One month, two Florida State losses, and one week’s worth of NFL games later, New Yorkers are mercifully still unable to use the app and Penn’s bungled stewardship of ESPN Bet continues to look worse and worse.

New York is but one state, though it is one of the biggest in the U.S. market. The state’s tax revenue on gambling, as of Sept. 7, was $653.7 million, which is more than the take from next eight largest states combined. The Penn optimist would read that datum as an opportunity, one that frames ESPN Bet’s nationwide struggles as an irrelevant prequel to the real game that begins once the venture gets going in New York. On the other hand, the person who understands how numbers work would point to, per Bloomberg, ESPN Bet’s 2.8 percent market share and the difficulties Penn has had increasing that number anywhere in the country.

Like the rest of the U.S., the New York sports gambling market is dominated by DraftKings and FanDuel. The two behemoths control roughly 75 percent of the market, with the new Fanatics sportsbook making some mild gains through the first half of 2024. The power that the DraftKings/FanDuel duopoly has is significant, as many would-be challengers have tried and failed to compete with it before shutting down, including FOX Bet; SI Sportsbook; Wynn, which sold its New York license to Penn in March after being totally unable to crack into the market; and of course, the Barstool Sportsbook, which flopped so bad that Penn gave the whole company back to its repugnant owner for $1.

The two-part lesson there should have been pretty clear: While regulated gambling is an extremely lucrative enterprise in its infancy, it is not an open market, and established sports media branding is not a strong enough gravitational force to dislodge consumers who got going on the apps that were there at the start. Shortly after ESPN Bet launched, Snowden set the target at 20 percent market share, which now seems laughably high. Industry analysts have framed this 2024 football season as a make or break year for ESPN Bet; the company has already ceded the first-mover advantage to its former partners DraftKings and their archrival FanDuel. Failing to get off the ground by Week 1 of the NFL season puts ESPN even further behind, as any new gamblers who were not betting last season but are betting this season necessarily are doing so with ESPN Bet’s competitors. The NFL is the most gambled-upon sport in the country, and given how obvious the power of being there first is, having the ESPN Bet app’s launch held up in the regulatory process is a pretty serious threat to Penn’s whole plan.

The logic behind ESPN Bet is that it can leverage ESPN and its significance within the sports broadcasting world to onramp people onto the app and away from their money. That line of thinking makes a certain amount of grim sense, even if the practical application is pretty horrifying to behold—but I don’t think it’s flawless. The sports gambler and the sports fan are not necessarily the same person. As money is involved here, it seems optimistic on Penn’s part to assume that people will simply choose to gamble where it is most convenient rather than where it is most efficient. I asked a couple of the sports gamblers on Defector’s staff why they wager where they do, and they cited better promos and earlier availability.

If ESPN Bet is to succeed, in New York or really anywhere, it will either have to shear away people away from the places they already bet on sports—a proposition whose dubiousness is well established by the graveyard of betting apparatuses—or pull off something far more sinister and difficult: create a new class of gamblers out of the uninitiated mass of ESPN consumers. Expect the already-sludgy ESPN experience to get even more dire, but don’t necessarily expect it to work.

CORRECTION (2:45 p.m. ET): An earlier version of this blog stated that New York state was the U.S.’s largest gambling market, but the size disparity in tax revenue between it and the rest of the states is largely due to New York’s higher tax rate, rather than the size of the statewide gambling handle.