I’ll refrain from further free promotion (the owners – one of whom is a great Sligoman, Derek Tighe – don’t need my help, anyway) but us four seeking out a plan to simply sit and watch some live football over coffees and maybe a Bloody Mary decided this was exactly the vibe needed for the edgy frivolity of Arsenal v Manchester City.

Ten years ago, I wouldn’t have crossed the street, never mind the Manhattan Bridge, to watch this pointless pre-season encounter. I feel a little bit of shame, of course, but I also exist in a post-shame era. Big glossy sport has won and my resistance was always futile. And the New York Mets are awful this season so the usual August distractions are a little more limited.

We settled into our seats, ensuring the Arsenal supporter had the best view. The calm was pierced by sudden panic when the North London-born Gooner realised he couldn’t bet on the game using one of the local gambling apps.

Up until very recently, Ireland and UK gamblers in New York availed of VPN workarounds that helped the user trick overseas companies into thinking they were placing a bet from their jurisdiction.

But online gambling is fully legal in many states now, including New York, so the need to send wagers home has been nullified.

For the most part, anyway. An American sports fan would never contemplate betting on the US equivalent of the Community Shield so why would a locally based betting app offer the opportunity to bet on an irrelevant match a few thousand miles away? So with less than ten minutes to kick-off, the Arsenal fan was flailing.

In many ways, it still feels like the wild west here. The glitches are still being ironed out, the lucrative partnerships are rising and falling and the backlash has yet to start in earnest. In all these ways we are behind Ireland and the UK but the gap continues to narrow and this week saw a huge threshold crossed.

Four of the most famous letters in US sports are E, S, P and N. The original 24-hour sports television channel is in its fifth decade of operations and is enduring a downturn which would have been unimaginable even five years ago.

The Walt Disney Company owns ESPN and its controversial CEO Bob Iger is open about his concerns when it comes to the future of what is still a profitable and influential asset.

The slide of ESPN is directly related to the hollowing out of the revenue model which overly served them for so long. Put simply, ESPN was traditionally able to charge so-called carrier fees to cable companies across the US who would then pass that cost onto their customer. Whether you were an ESPN addict or never watched a minute of sport from one end of the week to the next, you were ultimately benefiting ESPN the same way and ESPN was able to charge the most.

With consumers cutting off their cable service in their millions, the trough has shallowed out and the thirstiest, fattest beneficiary has been slowest to react to the changing conditions.

Ultimately, ESPN will need to fully evolve (or devolve) primarily into a streaming service but on their way to that destiny, the Disney overlords are frantically figuring out how to make ends meet (which in their case is how to keep profits in the billion or so range). Cutting costs by firing some of their best behind-the-scenes employees has caused tremors.

And then on Tuesday, they took an alarming leap directly into the gambling industry by licensing the iconic ESPN brand to Penn Entertainment to create “ESPN Bet”, a wholly unwholesome outcome Walt and Roy Disney may not have been able to fathom when they were starting out a century ago.

According to a Wednesday earnings call handled by Iger, ESPN had spoken with several gambling companies, or sportsbooks in the US parlance, but Penn Entertainment’s offer of $2 billion over the course of the next ten years was the most favourable.

“Penn stepped up in a very aggressive way and made an offer to us,” Iger said. “That was better than any of the competitive offers by far.” 

Experts have indicated a little bit of concern over this roll of the dice from the Penn Entertainment side of things: their gambit of $1.5 billion in licence fees over the lifetime of the contract plus $500 million of stock options is only a billion and a half or so less than Penn’s total valuation.

In order to make the deal possible, Penn cut their ties with the controversial content company Barstool whose innate inability to avoid stock-damaging missteps forced Penn to return their goods at a likely depreciated value from what had initially been a half a billion dollar punt just over three years ago. Barstool owner Dave Portnoy got his toy back, made out like a bandit and regained the freedom to be a bad human being again.

But what of ESPN and what of the future of television if the sports channel’s traditional business of cable company carrier fees and advertising brings in $14 billion in revenue and $3 billion in profit and that represents a storm warning? If the greatest powerhouse in the history of US cable television has such a bleak economic outlook, what will the rest of them do? There are only so many Real Housewives to keep the fires lit.

The bigger ESPN Bet questions are how this will affect content. The Penn deal is a dramatic u-turn for a company that not so long ago avoided sports betting like an oncoming NFL linebacker. In 2019, Iger said he didn’t believe The Walt Disney Company would get “involved in the business of gambling, in effect, by facilitating gambling in any way”. He turned down offers from Caesars and DraftKings that would have reportedly netted the company as much as $3 billion so that looks a little like a missed opportunity in hindsight.

Disney will not directly run the ESPN Bet sportsbook as they have cleverly carved the asset away, presumably in order to make their morally dubious move a little more palatable to shareholders. The deal guarantees Penn “exclusive promotional services across ESPN platforms including programming, content, and access to ESPN talent.” So will this influence programming? And will there be conflicts of interest? Will ESPN employees be permitted to use their betting platform?

Some of their top NBA and NFL reporters who are lightning quick in their reception and dissemination of the biggest scoops in the industry will surely need to be careful of how their yarns move betting lines. They will be under increased scrutiny for fear of insider information spilling out in the seconds it takes to place a wager.

But this is our reality now. Sink with the deadweights or swim with a lifesaving gambling giant. ESPN Bet will be scrutinised heavily on every level but whatever the outcome, you can only imagine that sports gambling will keep increasing across each state where it’s becoming more and more legal and normal.