Penn Entertainment finalized its acquisition of Barstool Sports from The Chermin Group earlier this year for approximately $338 million, bringing with it the loyal, dedicated following of the digital sports and entertainment brand and now, the future of Barstool’s founder, however, is in doubt.

Dave Portnoy recently appeared on The Kirk Minihane Show and expressed uncertainty regarding whether or not he would reach a contract extension with Penn National. He is not sure what the brand’s parent company is thinking regarding his future, and he publicly opposed the firing of Ben Mintz earlier this month.

“Who knows where I’ll be in three [or] four years,” Portnoy said. “I think Dan [Katz], which I would say is very good for Barstool, is clearly locked in for a long time. He’s creating this huge fantasy factory there. I think it’s great for Barstool.”

Barstool Sports has launched a sportsbook that is in the midst of being licensed in different locales around the United States, and Portnoy is aware sports betting is a priority for Penn National over the ensuing years. If his contract was not renewed upon expiration, Portnoy would have to consider several options regarding what to do in the future.

“Would I just do a podcast a week that’s totally unfiltered? Would I enjoy doing that? Maybe,” Portnoy said, noting that his contract expires in a little less than 2 years. “There’s a part of me that thinks I’d be like, ‘Okay, I’m done.’”

One of the things he has considered though is launching a pizza review show on Netflix, perhaps similar to what Anthony Bourdain did during his time as a celebrity chef.

One thing he is not interested in doing is cultivating an entirely new media business, but he genuinely does not know what Penn National is thinking as it pertains to his future with the brand.

Certainly though, Penn National wants to ensure it retains gambling licenses, and having controversial Barstool Sports personalities could at times complicate the situation. Moving on from Portnoy has the potential to redefine the brand itself, something that could ultimately prove harmful in the eyes of its dedicated legion of consumers.

Another round of layoffs has gotten underway at Facebook’s parent company Meta. Among those being let go are three executives in sports-related roles.

Meta’s Director of Global Sports Partnerships Rob Shaw, Director of Sports Partnerships Kevin Cote and Dev Sethi all confirmed in LinkedIn posts on Wednesday that their positions had been eliminated.

Shaw and Cote had been at Meta and Facebook since 2014, while Sethi joined the company in 2015.

“Those years have been full of innovation and transition within the sports industry, and it was my great pleasure to be a leading advocate for how technology can bring people closer to their passion of sports,” Shaw wrote. Before Facebook, he was the vice president of content and media at Bloomberg Sports.

“I was fortunate to be surrounded by top notch people, and while it is emotional to say goodbye, I have no doubt our paths will cross again soon,” Cote wrote. He noted that working with various athletes, teams and leagues worldwide on business and social needs, partnerships with high-profile athletes, original programming, live sports and working on athlete partnerships were some of the highlights of his career.

Sethi expressed pride in the work he did at Meta and was thankful to work in a position he could put his heart and soul into.

“I’ve been lucky to marry my passion for sports with my professions for years now, and my hope is to continue that marriage in whatever lies ahead,” he wrote.

The shedding of these jobs is part of a larger swath of cuts at the social media giant. Some 20,000 jobs at the company are being eliminated, and that dates back to November when Meta laid off its head of media partnerships and regional leaders in Asia, the Middle East and Latin America.

Meta at one time had rights to broadcast MLB games live on Facebook. The company has partnered with leagues like the NFL and the NBA, as well as the UFC to bring sports-related content into Web3 and the Metaverse. But the focus has shifted away from live sports rights into AI and alternate reality.

If you consume HBO content exclusively through the OTT platform HBO Max, you got a bit of a surprise this week. While the company had been preparing users that HBO Max and Discovery+ were going to be merged into an app simple called Max, users were shocked to find out that the existing apps weren’t simply going to become Max. Instead, users had to go download a new app entirely.

Dan Le Batard wonders if that might spell doom for the rollout of the new service.

“What they’ve changed, Amin, is you have to go to a different place,” he told colleague Amin Elhassan on his Wednesday show. “It doesn’t just transfer over when you go to HBO Max, it says this isn’t working anymore. This is closed forever. You’ve got to go somewhere else. Your Internet is not going to connect here.”

While HBO Max’s sports content was minimal, Warner Bros. Discovery has bigger plans for Max. In addition to US Soccer, it is expected that the new app will be the exclusive home for some NBA matchups if the league’s deal with TNT is renewed.

That is a worry for the future though. This weekend, HBO will air the finale of Succession. Le Batard wonders how many people are going to miss it entirely due to confusion.

“You have to download another app. And I do believe they’re going to lose a good many people who just simply don’t know how to do this of a certain age. They’re not going to be able to get over there, get their password and figure this part out without the help of the kids.”

Certainly how many of those users disappear forever is of interest to the NBA and NHL, but both leagues have good relationships with Warner Bros. Discovery. In the case of the NBA, the relationship with TNT goes back decades. A clumsy rollout of a new app is not ideal, but it isn’t likely to cost WBD Sports in upcoming negotiations.