PENN Leisure, as soon as the unassuming Penn Nationwide Gaming with little greater than racetracks and regional ambition, has spent a long time leveling up from modest racing outfit to one in every of America’s largest on line casino and racing powerhouses. Alongside the way in which, the corporate scooped up properties with the keenness of a vacationer amassing souvenirs, typically strategic, typically just because they have been there.
Acquisitions alone didn’t fulfill the company urge for food. PENN additionally hurled itself right into a sequence of wildly bold partnerships, most lately with ESPN Guess, which it terminated on Thursday (November 6). Some shone for a wonderful second, whereas others collapsed beneath the load of excessive expectations, excessive prices, or altering market realities.
Briefly, the journey has been quick and bumpy.
PENN’s partnerships: early main failures
In 2006, Penn Nationwide took a swing at buying Harrah’s Leisure. The try fizzled out, however the message was clear: PENN was uninterested in being referred to as the plucky regional operator and was able to audition for a nationwide highlight.
Not lengthy after, within the heady days of 2007 and 2008, PENN went even larger and chased a $6.1 billion buyout that will have taken the entire firm personal. It was a grand imaginative and prescient, the sort of transfer that makes bankers shareholders pretty nervous. The deal collapsed earlier than the ink even considered drying, an indication that early efforts at sweeping reinvention and excessive stakes transformation have been already bumping into actual world turbulence.
Barstool Sports activities: a meteoric rise adopted by a speedy unwind
In 2020, PENN got here again into the highlight and snapped up a 36% stake in Barstool Sports activities for about $163 million, full with an choice to purchase the entire circus inside three years. The partnership generated monumental buzz. PENN’s inventory shot upward after the announcement, promptly collapsed when the pandemic hit, then rocketed to all time highs as soon as the Barstool Sportsbook app arrived to distract traders from actuality. By early 2021 the inventory was up practically 400% in contrast with the 12 months earlier than, a efficiency Wall Road analysts described as outstanding and everybody else described as probably supernatural.
Nonetheless, the Barstool relationship proved unstable. PENN went forward and purchased the complete firm in early 2023, solely to hand it again to founder Dave Portnoy just a few months later for the princely sum of 1 greenback. The transaction appeared much less like a sale and extra like the company model of sliding the keys throughout the desk whereas saying please take this off our palms.
In the long run, PENN accepted substantial losses in change for a clear break from a model that got here with nonstop controversy and sufficient regulatory complications to maintain a number of attorneys employed for eternity. The retreat was complete, the lesson costly, and the publish breakup silence was in all probability very peaceable.
ESPN Guess: a excessive profile partnership that ended early
In August 2023, PENN rolled out a ten 12 months settlement with ESPN that will rework its sportsbook into ESPN Guess. Public estimates put the worth tag at round $1.5 billion {dollars}. The thought appeared easy on paper. The corporate would supply the playing equipment, ESPN would supply the big sports activities viewers, and collectively they’d create a blockbuster betting model that will dominate the nation.
Massive Information! This soccer season, @ESPNBET is bringing collectively media, betting and fantasy like by no means earlier than with FanCenter, a brand new devoted hub inside ESPN BET that can take personalization to the subsequent stage. pic.twitter.com/y7Fe0phrDa
— PENNEntertainment (@PENNEntertain) August 4, 2025
PENN launched ESPN Guess in seventeen states in November 2023 and stored including extra jurisdictions in 2024. For a quick second, the rollout felt like the beginning of a brand new period, the sort the place executives give inspirational speeches and everybody nods as if they’re witnessing historical past.
Then the numbers arrived. By late 2025, publicly obtainable knowledge confirmed that ESPN Guess had secured solely a sliver of the US on-line sports activities betting market. This was considerably lower than the sweeping share PENN as soon as envisioned. The monetary logic of the complete enterprise began to wobble. Analysts whispered, shareholders frowned, and accountants in all probability developed migraines.
Finally, PENN and ESPN agreed to name it quits early, with the partnership formally ending on December 1, 2025. PENN will cease making funds to ESPN after the fourth quarter of 2025 and can revive its sportsbook beneath the corporate’s present theScore Guess identification through a rebrand.
Attainable causes of repeated partnership failures
A number of unmistakable themes emerged from PENN’s rising assortment of in poor health fated partnerships. Time after time, the corporate tried to harness the star energy of main media manufacturers as a way to crash the gates of the web betting world. In idea, an enormous media identify ought to unlock prospects by the truckload.
In follow, a shiny emblem didn’t magically flip informal viewers into loyal bettors, regardless of what number of promotional codes fluttered throughout their screens. The monetary construction of those preparations made issues even messier. Every deal demanded heavy up entrance spending or long run cost commitments that grew to become more and more painful when the anticipated income refused to indicate up.
The broader panorama was not doing PENN any favors both. The US sports activities betting market modified so shortly that even seasoned analysts wanted seat belts. New opponents crowded in, state rules shifted like sand, and the price of buying prospects stored climbing. The outcome was an setting the place even well-known sportsbook manufacturers had hassle attracting giant consumer bases, not to mention retaining them round. PENN was not alone in feeling the squeeze, however its excessive profile partnerships made the stress way more seen and much costlier.
What comes subsequent for PENN
PENN now says it’ll flip its consideration again to the elements of the enterprise that really pay the payments. Meaning a renewed deal with on-line on line casino operations and the sturdy regional on line casino empire that has carried the corporate for many years. In latest disclosures, management defined that ending the ESPN settlement will give PENN a cleaner price construction and unlock money for areas that provide actual, sustainable alternative. This implies it’s time to cease renting another person’s star energy and begin investing in what already works.
The following problem is much much less glamorous however way more vital. PENN should show that it may generate momentum with its personal manufacturers and its personal platforms. No superstar companions, no splashy media alliances, no billion greenback shortcuts. Only a firm, its prospects, and the lengthy highway again to a method that doesn’t contain handing over piles of cash for another person’s emblem.
Featured picture: PENN Leisure
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