Barstool Sportsbook Review
by
Eric Uribe
The Barstool Sportsbook ceased operations in November 2023. The sportsbook was a joint venture between Penn Entertainment and the controversial Barstool Sports media brand. It’s this same controversy that helped the platform get off the ground in the first place but also led to the two companies splitting from each other for “greener pastures” per se.
There is still plenty of interest around the Barstool Sportsbook so we’ve compiled a quick guide to what happened, why, and what lies ahead for both companies and bettors.
What Happened To The Barstool Sportsbook?
In August 2023, bombshell news dropped courtesy of Penn Entertainment. In one fell swoop, they announced they had signed a 10-year, $1.5-billion dollar deal with ESPN for a sportsbook license. In the same announcement, Penn announced it was selling Barstool back to founder Dave Portnoy for a whopping $1. In other words, ESPN was replacing Barstool as Penn’s sportsbook brand.
A few months later, the newly branded ESPN Bet officially replaced the Barstool Sportsbook app. While the core betting experience remained largely the same with ESPN’s branding, users at the time had to download the new app manually since it didn’t convert through an automatic update.
Any users with an existing Barstool sports book are automatically “grandfathered” into ESPN Bet. This means that the same login credentials work on ESPN, and any leftover funds and saved payment methods are transferred over automatically. All in all, it was a smooth transfer all things considered.
Why Did Penn Sell Barstool?
The Barstool sportsbook did have an imprint on the online sportsbook industry. Barstool Sportsbook was live in 15 states at its peak, including Indiana, Michigan, and several others. Despite this reach, the platform never gained enough traction for Penn to compete with the top market leaders.
You see, the Barstool betting platform never quite lived up to expectations. You can’t pin that on one issue, but a few different ones. Let’s count down why Barstool Sportsbook ultimately failed.
When Penn spent $550 million to acquire Barstool’s entire company, the thought was “Stoolies” — fans of the brand as they call themselves — would be cheap customers to convert into bettors. Whereas DraftKings and FanDuel were spending billions to acquire new customers via marketing and lucrative sportsbook bonuses, the Stoolies would support the sportsbook in droves for a fraction of the cost. That never really transpired. And even the Stoolies that did join, most trend younger and with less disposable income, not the most lucrative market for a business.
Not only that, but most of the Barstool review were hardly favorable — among bettors and sites like ours. The overall user experience just paled in comparison to competitors, a problem that now exists for ESPN Bet.
Not only that, but being “in bed” with Barstool created regulatory problems for Penn. Whether accurate or not, Barstool’s reputation isn’t exactly noble — racist, misogynistic, vulgar, and mean spirited are all words used to describe Barstool. This created a challenge for Penn when trying to acquire state licenses to operate in.
Even in Massachusetts, where Barstool started, state regulators criticized Barstool’s famous “can’t lose parlay” joke. Staff members, famously Dan Katz, used the three-word phrase to describe his parlay picks. Funny, yes, but not regulatory safe either. Eventually, the joke was dropped entirely out of regulatory concerns.
There was also an incident when Barsrool staff member, Ben Mintz, accidentally dropped the n-word during a live show. Portnoy publicly blamed Penn for having to fire him, which couldn’t have helped the relationship at all.
Portnoy put it best himself: “We underestimated how tough it was to operate in a regulated world.” The Barstool ethos just didn’t mesh with the heavily-regulated world of sports betting AND a public company, hence the split.
Will Barstool Sports Betting Continue Elsewhere?
What is Barstool’s future now? As of 2025, the company is fully independent again after years under corporate ownership — first with the Chernin Group and later Penn Entertainment. True to form, Barstool has leaned back into its unapologetic, non-politically correct brand identity, doubling down on content rather than operations.
When it comes to sports betting, Barstool has not relaunched its own sportsbook platform, and there’s little indication it ever will. The original Barstool Sportsbook model proved costly and unsustainable, and Penn’s pivot to ESPN Bet closed that chapter for good.
Instead, Barstool has carved out a profitable lane as an affiliate partner. The company continues to push betting-related content to its massive fanbase and now earns revenue by directing users to other major sportsbooks through affiliate deals and promo codes — a model that fits its media-first DNA.
You might want to read our ESPN Bet review if you want to see how Penn moves forward post-Barstool Sports too. They have a ways to go to catch up to industry leaders, but having ESPN’s brand could be a huge boost to their efforts.