Imagine one night you’re watching Anderson Cooper on CNN. He’s talking about how the president is slapping tariffs on the Republic of Ruritania because Ruritania subsidizes the production of widgets “VERY UNFAIRLY.”
The stock market plunged following the announcement. Now you’re watching Anderson Cooper intently, listening to him and a panel of respected experts break down the decision and what it means for the average American. You never knew Ruritanian widgets were so important. You think, “wow, my local widget-processor is really going to take a hit from this!” One expert warns that this could just be the beginning, more widget-related tariffs could be coming.
Finally, Anderson calls for a break in the action. He turns to the camera. You’re hanging on his every word. What is it, Anderson? Tell me: WHAT ARE WE GOING TO DO ABOUT THIS RURITANIA SITUATION?
Anderson takes a breath, and in his perfect news voice says: “Do you think you can predict who the president will put tariffs on next? Well, you can go to CNN BET now and put your money where your mouth is. Use promo code TARIFF and you could get 20 CNN Bucks back if your first prediction is wrong! OK, we’ll be right back with our prediction expert, Johnny Predicts, to handicap these tariff markets. He’s even got a tariff parlay!”
You’re sitting on your couch now, after seeing and hearing one of the most trusted names in news read you a betting ad. What runs through your mind? Is it “Oh, baby, 20 CNN Bucks! Let’s go!” Or is it more like… “What the hell was that? Did Anderson Cooper just tell me to gamble? Why? Was that whole segment just to get me to make a bet?”
CNN senior political commentators Van Jones and David Urban talk about the challenges ahead for NYC mayor-elect Zohran Mamdani. pic.twitter.com/8yBzE4q0Wi
— Anderson Cooper 360° (@AC360) November 6, 2025
Again, this hasn't happened (at least I don’t think it’s actually happened). Maybe someday it’s possible, sure, what with the rise of prediction markets facilitating wagering on all kinds of stuff. But, for now, the above is still a product of my imagination. Anderson Cooper is not the pitchman for a prediction market (that I’m aware of).
Consider this imagined scene, though, in the very real context of ESPN and ESPN BET, the product of a partnership between ESPN and PENN Entertainment. The online sports betting brand is now being wound down, despite launching less than two years ago and after millions of dollars were burned trying to propel it onto the podium of legalized mobile wagering. It didn’t happen. It also didn't happen after PENN tried a similar marketing partnership with Barstool Sports.
So ESPN and PENN have decided to go their separate ways. I think it’s for the best. I also think it’s a costly lesson of why it pays to stay in your lane.
A win-win (if you ignore the lose-lose)
Let’s start with ESPN. If there’s a CNN for sports, it’s ESPN. It’s where you get sports, sports analysis, news, and information about sports. You expect certain things from ESPN. You want certain things from ESPN.
You want Adam Schefter dropping a huge scoop about an NFL player being traded. You may want some X’s and O’s analysis from NFL experts. You may want a lot of stats and data, maybe even the lines and odds for games, because those, too, are interesting data points. Wow, Buffalo is favored by how many points this week?
Sports bettors want stuff from ESPN, too. Maybe there’s news you can use to handicap a game or insights that help you recalibrate your approach. And, most of all, you want ESPN to show you the games you’re betting.
What someone may not expect or want is ESPN personalities and programming that they’ve long trusted suddenly trying to talk gambling and directing you to an ESPN-branded sportsbook. Now you feel like you’re being sold something, nudged toward wagering with an ESPN-branded product, and by people who didn’t do that before. If you don’t bet (and a lot of people don’t bet), you may be annoyed. If you’re a bettor, you may be annoyed as well, because what do any of these people know about gambling?
In short, who wants an ESPN that talks a lot about betting and then touts an ESPN-branded sportsbook? Do sports fans? Do sports bettors? In my mind, it’s supply in search of demand.
Just trust me
ESPN may also be running the risk of undermining trust in what it’s saying by pushing betting too hard. People have lost their minds in the past over reporting on the NBA Draft, for example. Gallup also found recently that Americans' trust in mass media has hit a new low. A YouGov survey published this week suggests a majority of Americans have had at least a passing thought that professional athletes are altering their performance to cash bets. A source of sports news may risk its reputation and standing with its audience by being too aggressive with sports betting.
ESPN had to know this, and may have restrained itself somewhat as a result. You don't want to get hammered as shills, but you must shill, that's what the marketing partnership was for. You were damned if you did and damned if you didn't.
But now ESPN, by backing away from an ESPN-branded sportsbook, has an opportunity to own that role as the CNN of sports. You can absolutely still talk about sports betting, because that is a significant part of sports now. You can mention the odds, you can mention someone’s a huge underdog, you can point out bad beats, you can report on the controversies and scandals. In fact, you absolutely must report on the controversies and scandals. And, yes, you can run ads for sportsbooks. You may even get more eyeballs on them if your editorial content stays strong, above reproach, and with no trace of conflict.
Just be selective. Don’t beat people over the head with gambling. Don’t make people who don’t know gambling talk about gambling. Don’t put yourself in a situation where you must suddenly disappear a gambling graphic because the news of the day is about gambling and it might be awkward to advertise a sportsbook. Let bettors and non-bettors take in your sports content, digest it, and then determine if they’d like to bet.
ESPN quickly removes ESPN Bet banner during coverage of NBA gambling arrests https://t.co/lpFkCARlaw pic.twitter.com/2mz5HVoj86
— Awful Announcing (@awfulannouncing) October 23, 2025
In short: stay in your lane. Your lane is good! Your lane has value for bettors and non-bettors alike! People like what’s in the lane. If people want gambling stuff, they can find it in a lot of places, including this website (full disclosure: we talk about sports betting a lot here, that’s kind of our business, and I fully admit to a bias toward Covers, my employer). People bet when they have opinions. Help them form opinions without force-feeding it to them with promo code chasers, because that may not be what they're expecting form you.
The word I’m probably searching for here is authentic. Be authentic. To thine own self be true, ESPN. ESPN talking about betting is fine in moderation. ESPN-branded sports betting can be conflicting.
DraftKings had discussed partnering with ESPN to replace ESPN BET as the platform's exclusive sportsbook media and odds provider as early as February, per @Bill_KingSBJ
— Ryan Butler (@ButlerBets) November 7, 2025
PENN, meanwhile, has another chance to squarely get back into its lane, which IS gambling, and more specifically, casino gambling. PENN runs casinos. It also runs sportsbooks. Gambling is what PENN does and what people expect PENN to do.
However, PENN knows that casinogoers are getting older. In this context, pairing up with media partners like Barstool and ESPN makes sense, because you can reach people who may not go to casinos, who want to gamble online if at all. Having Big Cat and Scott Van Pelt in your corner talking gambling and directing younger people toward your online sportsbook seems logical.
“The average age of our casino customers is in the mid-50s,” PENN CEO Jay Snowden once told investors. “How do we solve for that? Sports betting.”
So I think that thesis makes some sense, but the reality is much more challenging and costly. PENN was fighting for market share with DraftKings and FanDuel, who were basically grandfathered into online sports betting and got to bring their DFS customers along with them. Newer players like bet365 and Fanatics kept popping up and gaining traction, pumping even more promotional dollars and marketing money into the equation. Now along have come prediction markets, another competitor and one that is in states that PENN can’t access and may not want to access, for fear of upsetting its brick-and-mortar regulators.
In other words, PENN’s desire for online sports betting success was always going to be difficult. Just ask everyone who isn’t DraftKings or FanDuel, and even those two may feel a little less secure these days because of prediction markets. And yet, PENN spent hundreds of millions of dollars trying to make a go of it, and veered into areas where it isn't the expert, namely, media.
PENN’s detour from its lane also gave the company headaches it may not have expected. Most notably, PENN was called on the carpet by regulators in Massachusetts for marketing missteps by its partners, whose talk of “Can’t Lose” parlays and “risk-free” investments were jokes, but not ones that everyone found funny. You can't disavow knowledge or responsibility from brands when you've clothed your sportsbook in them.
A for effort
You could at least say that PENN tried. But PENN is now going to try something I think lines up much better with what PENN actually is: a casino company. And perhaps a pretty good casino company at that. PENN’s interactive segment may be down $227.6 million in adjusted earnings for the year, but that's more than made up for by the $1.4 billion in adjusted earnings from its regional casino segments. And people are complaining about Vegas being too pricey these days! While that may be up for debate, it looks like a good time to run casinos much closer to home.
What PENN also plans to do now is a "realignment" of its digital operations, "to leverage the strength of our U.S. iCasino and Canadian operations."
This also makes sense to me. If and when people think about PENN, they probably think about casinos. If people are looking to play online casino games, using a Hollywood Casino-branded app is a logical leap for those people to make. PENN even has a good news story to tell there, having reported this week that its North American iCasino business is seeing double-digit growth in users and revenue.
PENN's online sports betting journey (part of it, anyway):
— Geoff Zochodne (@GeoffZochodne) November 6, 2025
-2020: Partner with Barstool, pay ~$163M for 36% stake
-2021: Buy theScore for ~$2B
-Feb. 2023: Buy rest of Barstool for ~$388M
-Aug. 2023: Form new,~$2B partnership with ESPN, Barstool sold back to Dave Portnoy for $1…
Citizens analyst Jordan Bender wrote in a note to clients on Thursday that the move to an "iGaming-first philosophy" is something that is "proving to be a success for companies like Caesars and Rush Street."
PENN also has an edge in Canada, which is theScore. Maybe theScore as a brand doesn’t resonate as widely with Americans, but for me, a Canadian, it means something. I use it basically every day to check actual game scores. It is also tied to an online sportsbook and casino, theScore Bet. The tech is good, to me anyway, and allows you to go from checking scores to making bets with relative ease.
Leaning into Canada makes sense, then, for PENN. It has an asset in theScore (the online betting brand of which may not be as strong in the U.S., but could catch on and have some success). Its online gambling business is also in full swing already in Ontario and plans to pull out all the stops for Alberta, when that province eventually launches a regulated iGaming market. Jay Snowden even suggested during this week that PENN would consider land-based opportunities in Canada should they arise.
I’m not a business genius, so maybe I should stay in my lane as well, but I think casinos and Canada look like a good lane for PENN. You're a casino company, you own a great sports brand in Canada. Use that. Trying to take on the online sports betting duopoly in the U.S. by enlisting trusted media personalities watered down their best assets and yours.
However, after all the money spent to get to this point, the biggest question for PENN may be how patient everyone will be with the latest lane-change. I will leave that determination to whoever is in that lane. I’ve strayed far enough.
Here's your tl;dr, though: ESPN, do sports. PENN, do gambling. If people want either, they'll find you. Especially if you're the best at what you do.
