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 all 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 accumulating 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 formidable partnerships, most lately with ESPN Wager, 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 often called 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 may have taken the entire firm non-public. It was a grand imaginative and prescient, the type 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 fast 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 possibility to purchase the entire circus inside three years. The partnership generated huge 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 buyers from actuality. By early 2021 the inventory was up practically 400% in contrast with the 12 months earlier than, a efficiency Wall Avenue analysts described as outstanding and everybody else described as presumably supernatural.
Nonetheless, the Barstool relationship proved unstable. PENN went forward and acquired the whole 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.
Ultimately, PENN accepted substantial losses in alternate for a clear break from a model that got here with nonstop controversy and sufficient regulatory complications to maintain a number of legal professionals employed for eternity. The retreat was whole, the lesson costly, and the put up breakup silence was most likely very peaceable.
ESPN Wager: a excessive profile partnership that ended early
In August 2023, PENN rolled out a ten 12 months settlement with ESPN that may rework its sportsbook into ESPN Wager. Public estimates put the value tag at round $1.5 billion {dollars}. The concept appeared easy on paper. The corporate would offer the playing equipment, ESPN would offer the large sports activities viewers, and collectively they’d create a blockbuster betting model that may 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 may take personalization to the following stage. pic.twitter.com/y7Fe0phrDa
— PENNEntertainment (@PENNEntertain) August 4, 2025
PENN launched ESPN Wager in seventeen states in November 2023 and saved including extra jurisdictions in 2024. For a short 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 out there knowledge confirmed that ESPN Wager had secured solely a sliver of the USA on-line sports activities betting market. This was considerably lower than the sweeping share PENN as soon as envisioned. The monetary logic of the whole enterprise began to wobble. Analysts whispered, shareholders frowned, and accountants most likely 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 current theScore Wager id through a rebrand.
Attainable causes of repeated partnership failures
A number of unmistakable themes emerged from PENN’s rising assortment of ailing fated partnerships. Time after time, the corporate tried to harness the star energy of main media manufacturers with a view 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 brand 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 fee commitments that turned more and more painful when the anticipated income refused to point out up.
The broader panorama was not doing PENN any favors both. The USA sports activities betting market modified so shortly that even seasoned analysts wanted seat belts. New opponents crowded in, state laws shifted like sand, and the price of buying prospects saved climbing. The consequence was an atmosphere the place even well-known sportsbook manufacturers had bother attracting massive person bases, not to mention maintaining them round. PENN was not alone in feeling the squeeze, however its excessive profile partnerships made the stress much more seen and much costlier.
What comes subsequent for PENN
PENN now says it would 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 current disclosures, management defined that ending the ESPN settlement will give PENN a cleaner price construction and unencumber money for areas that supply actual, sustainable alternative. This implies it’s time to cease renting another person’s star energy and begin investing in what already works.
The subsequent problem is much much less glamorous however much more vital. PENN should show that it will possibly 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 street again to a technique that doesn’t contain handing over piles of cash for another person’s brand.
Featured picture: PENN Leisure
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