Earlier this summer, Fox Sports CEO Eric Shanks jetted into Nantucket for a three hour meeting that would reshape the lineup of Fox Sports 1, and shake up its Big Noon Kickoff college football show.

Shanks’ brief visit to the New England vacation destination was to help close a deal with Dave Portnoy and his digital media brand Barstool Sports. Portnoy’s $42 million compound on Nantucket (the most expensive home ever sold in the state of Massachusetts when he bought in 2023) overlooks the harbor, where ferries bring visitors and residents in and out from the mainland all day. All paid for by his self-described “pirate ship” of a media brand, which he had sold to Penn Entertainment for $551 million, and bought back just a couple of years later for $1.

Shanks’ visit underscores how the sands have shifted in media. It wasn’t that long ago that talent would be summoned to meet with execs in their New York offices or Los Angeles studio lots. Now when there is talent in demand, the executives will go where they need to, even an island 30 miles out in the Atlantic Ocean.

Fox had been chatting with Portnoy for “five or six months,” the Barstool founder said on his company’s Unnamed Show on July 17, culminating in the deal announced the same day, which will see Portnoy appear weekly on Big Noon Kickoff and Barstool creating a live two hour show for FS1, as well as social content.

“We had that ESPN deal, they didn’t even want to talk to me, right? They couldn’t stomach the sight of my face,” Portnoy said on the podcast, referencing Barstool Van Talk, the ESPN2 series that was canceled after one episode after the network became uncomfortable with comments made by talent on social media. “[Fox] wants our audience, they know what audience we have, and we’re going to try to come up with a bunch of things with them. And it’s a wide-ranging relationship.”

The world of media has changed, and authenticity rules. Being outspoken is even better, and with cord-cutting wreaking havoc on TV viewing, traditional TV players that used to develop their talent in house are increasingly turning to outsiders to help give them relevance to an audience that might otherwise bypass their content.

“Dave has built a one-of-a-kind brand that connects with a new generation of sports fans – authentic, bold, and original,” said Shanks in a statement. “[Barstool’s] unique voice and loyal fanbase makes them a natural fit for our evolving multiplatform content strategy.”

A lot has changed since ESPN canceled its Barstool show in 2017. Look no further than ESPN’s deals with NFL player turned radio and podcast host Pat McAfee (who cut his teeth in digital media at Barstool, no less).

McAfee has occasionally found himself in hot water, like when he accused ESPN executive Norby Williamson of “sabotaging” his show, or when recurring guest Aaron Rodgers made unfounded claims about Jimmy Kimmel and Jeffrey Epstein. Earlier in July, McAfee apologized to an Ole Miss student who was named in a viral but false internet scandal (Portnoy also apologized for some of Barstool’s talent spreading the false report).

Sitting on a panel in ESPN’s commissary in Bristol, Connecticut last year, McAfee exuded confidence as he parried questions from skeptical journalists about his deal, which sees ESPN license The Pat McAfee Show, an unusual arrangement for a daily program.

“We haven’t been kicked off ESPN yet, I view that as a success. Now, granted, we would still just continue doing business on YouTube and on our TikTok and everything like that, and we’re very lucky to be on ESPN,” McAfee said. “Whenever people in here have tried to get me fired for taking clips out of context or quotes out of context, and misrepresented everything that I’ve said, and the human that I am and the deal that it is, we know that we’re good. So you can fire us, you can try to kill us, you can do whatever you need to do. But our success is the fact that we have a following, and they’re going to ride with us.”

ESPN chief Jimmy Pitaro said that he has been laser focused on the problem of “how can we resonate with younger people?”

“If you look at my kids, Netflix, Instagram, TikTok, Fortnite, they’re incredibly distracted. So how is it that we can make programs like Get Up and First Take resonate with younger people? Obviously, Pat McAfee is very, very helpful there,” Pitaro said. “I was just in a research meeting where our folks presented to me the response that younger people have had to Pat McAfee, and it’s been staggering and really helpful to our brand in its entirety.”

The talent benefits too. Portnoy told his company’s podcast that they are already thinking about how Fox talent like Greg Olsen and Tom Brady could participate in Barstool segments, while McAfee says that “we got legitimized by ESPN.”

“Some suits that wouldn’t let their clients come on our show before, because we were just an internet show,” he said.

Sports media, with its hot takes, fierce debates and big personalities has been a natural proving ground for TV’s digital creator era (consider Omar Raja, the House of Highlights founder who also joined ESPN in 2020), but there are signs that TV news is the next frontier. Brett Cooper, a popular YouTube creator who blends entertainment and cultural commentary with conservative values, was signed as an on-air contributor to Fox News.

“It’s about connecting with the audience, first and foremost,” says Lauren Petterson, president of the Fox Nation streaming service and head of talent development for Fox News. “Brett does that through her cause – which is culture. And the way she does it is also unique, through thoughtful discussion and persuasion. She is also a very direct person: she’s consistent with what she says and what she’s doing in her own life. She’s the same person on the screen as she is in person. That kind of authenticity appeals to people of all ages.”

Fox also recently cut a deal to license the Ruthless podcast, with executive Porter Berry adding oversight of new media as the company seeks out other digital deals.

And Skydance has held conversations with Bari Weiss about possibly acquiring her Free Press, perhaps bringing the outspoken former New York Times columnist into the CBS News fold when it takes over Paramount, in a bid to expand its digital footprint (or maybe to comply with promises made to the FCC).

“Skydance has made written commitments to ensure that the new company’s programming embodies a diversity of viewpoints from across the political and ideological spectrum,” FCC chairman Brendan Carr said in a statement approving the deal. “Skydance will also adopt measures that can root out the bias that has undermined trust in the national news media.”

Weiss, a frequent critic of the mainstream media, could fit that bill.

And both CNN and MSNBC are in the midst of a podcast expansion push, with MSNBC hiring executives to beef up its digital business ahead of its spinout into Versant later this year.

Both cable news channels are leveraging their own talent, of course, but there are signs they are looking elsewhere too.

Last year, podcast hosts Kara Swisher and Scott Galloway (someone also known for his hot takes) held talks with CNN about moving their show into its orbit, before reupping with their current partners Vox Media.

There is connective tissue between all of these conversations and deals. Cultural currency is more likely to be found these days on YouTube or Spotify, and viewers of live linear TV tend to skew older. With news and sports the last content standing, bringing over some of that more youthful audience could be a way to extend the lifespan of linear TV as executives grapple with a saturated and splintered streaming environment.

And with YouTube increasingly taking over the TV set, news executives are beginning to grapple with a world where the shows are just one of thousands being fed algorithmically to viewers. Perhaps its better to have those creators that figured out how to make that model work inside the house, before the whole thing collapses into itself.

This story appeared in the July 30 issue of The Hollywood Reporter magazine. Click here to subscribe.