PENN Entertainment and ESPN Partnership Set to Bring Hollywood iCasino and ESPN Bet to Michigan

Jessica Aletor
Jessica Aletor


  • On Tuesday August 8, PENN Entertainment announced the sale of Barstool Sports and an exclusive deal with ESPN.
  • This agreement will bring ESPN Bet to Michigan while also heralding the launch of a Hollywood Online Casino in the state.
  • ESPN Bet is scheduled for launch later in November at the midpoint of the football league season, but regulatory uncertainties remain.

PENN Entertainment signed the “deal of deals” in the second week of August. While corporate restructurings and partnerships have been a pretty common phenomenon in the last two years, some are more noteworthy than the others. In the late hours of August 8, 2023, PENN Entertainment announced to the public that it had entered into an exclusive partnership with ESPN.

The details of this deal involves the arrival of Hollywood iCasino in Michigan. PENN Entertainment has also resold Barstool Sports and is set to launch ESPN Bet as its replacement in the state. PENN had recently upgraded the Barstool Sportsbook and online casino apps, but poor profitability triggered the need for a sale.

Dave Portnoy Buys Back Barstool Sportsbook Michiganders Anticipate ESPN Bet

Portnoy founded Barstool Sports back in 2003 and has seen majority shareholders change hands multiple times in the last decade. The Chernin Group were the first to buy a majority stake in 2016 until PENN Entertainment secured a 36% buyout stake from the company in 2022. PENN Entertainment would later buy off the rest of the company's operations in February this year.

Interestingly Portnoy repurchased his company for just a dollar, with the deal including non-compete agreements and a term that would see PENN earn 50% if Barstool was sold again. What this means for the Michigan online gambling industry is that Barstool’s operations will be replaced by another brand. As it stands ESPN Bet will take over the sports betting operations while Hollywood Online Casino will be the perfect iGaming replacement.

Speaking about the arrival of a Hollywood Online Casino, the CEO and President of PENN Entertainment revealed the following at the company’s Q2 investment call:
“We will have a Hollywood-branded iCasino offering within the ESPN Sports betting platform in all states where online casino is legal. We thought it was a good time for us to pivot to really focusing on Hollywood casino and the Hollywood brand. The Hollywood brand for us on the brick-and-mortar side is roughly two thirds of our properties. We invest a lot of capital across the portfolio there and so we’re very proud of that Hollywood brand. We think that it creates a really nice linkage from digital online casino, in the five markets that we’re live in today, and that’s going to grow over time.”

Despite the financial prospects of a Hollywood Online Casino, it has barely made the news like the arrival of ESPN Bet has. This is partly because more states have legalized sports betting compared to those with legal online casinos. So, the impact of ESPN Bet is more directly felt.

ESPN Bet is expected to launch in November, right at the middle of the 2023-24 NFL season. However, it is uncertain if Hollywood Online Casino will go live in that same period.

PENN Entertainment Forced to Sell Barstool Despite Recent Platform Upgrades

The sale of Barstool is quite intriguing as PENN had only acquired the entirety of the company this year. Besides, it upgraded the platform as recently as July.

“During the quarter as I briefly mentioned earlier, we successfully completed the full-scale migration of our US digital sportsbook and online casino offerings to our proprietary in-house technology platform, which was a huge milestone achievement for our company. The state-of-the-art tech platform continues to drive strong results for theScore Bet in Ontario, and our improved product will provide the foundation for meaningful growth in the US. Once we rebrand to ESPN Bet later this year,” Snowden said.

However, poor profits forced the resale. The casino holds only 3.2% of the Michigan iGaming market share. While the sportsbook had fared better, the overall numbers did not make keeping the brand a viable idea for PENN.

Hollywood Casino May Require Additional Regulatory Approval Before Launch

Many speculators expect that Hollywood iCasino may hit a regulatory bump during launch in Michigan. Although PENN Entertainment possesses a commercial gaming license in the Great Lakes State, ESPN and Hollywood Casino do not. However, the MGCB has declined to give any direct information about what regulatory procedures are next.

“It is premature at this time to discuss what additional requirements PENN Entertainment, or any of its affiliates/partners, may have to meet as a result of this announcement,” representatives of the Board remarked.

Judging from Barstool’s prior engagement, it is believed that ESPN and Hollywood may also need a vendor exemption to operate in Michigan.

Jessica is a news contributor to Gamble Online Michigan. She holds a Bachelor's degree in Economics but has over three years of experience working in the hospitality and gambling industry. Despite her core finance and investment banking background, she has been a casino feature writer for N1 Interactive Limited and multiple gambling affiliate sites. Her work has been featured on the bet365 blog, and Max Force Racing. She spends her time between Michigan and California, staying up-to-date on the latest industry developments