Since Matthew Berry left ESPN in 2022, fantasy sports and gambling have arguably gotten even bigger.
Digital and television networks alike infuse their coverage with fantasy, betting, and prediction market commentary, and nearly every one has its own lucrative sportsbook sponsorship — including ESPN. At the same time, ESPN (and some of its competitors) have become far more comfortable with bringing in outside talent to contribute to shows or even host their own.
In just a few short years, two of the big factors that had led Berry to walk away from the Worldwide Leader have flipped. Unsurprisingly, this has led Berry to revisit his relationship with the company.
Berry, who just finished a high-profile stint at NBC Sports and Football Night in America, revealed this week in an interview with Outkick that he has in fact had “multiple conversations” with senior ESPN leadership, though he stressed that nothing is “imminent.”
“I have a very good relationship with Jimmy Pitaro; with Burke Magnus, I remain friendly with them over the years since I left. Any time you go out on your own and you’re [saying], ‘OK, I’m now on my own, who are people that I can partner with, who are people that I like?'”
All of Berry’s content currently lives at Fantasy Life, the company he founded and built from the ground up. Fantasy Life has several subscription products and recently struck partnerships with Audacy and Prime Video to distribute its video podcasts.
Berry previously said his efforts with Fantasy Life were a problem for ESPN; that seems to have changed.
“When you leave, when you go out on your own, you’re looking for, McAfee is the great model. And they’ve done it; ESPN specifically has done it with a number of people,” Berry explained. “So you think about McAfee, Rich Eisen … and they have some other talent that they don’t necessarily license their show, but they allow them to have outside businesses, whether it’s, you think about Bussin’ With the Boys, Josh Pate is another example.”
When ESPN launched its first streaming service, ESPN+, nearly a decade ago, Berry’s puppet-filled series, The Fantasy Show, was among the first offerings. It remains one of the more creative and unique shows ESPN has ever produced; his current show is more straightforward, built around fantasy football commentary.
Though ESPN still airs Fantasy Focus, the massive hit Berry launched with the company, it has shown willingness to bring in shows that overlap in both content and scheduling. McAfee and Eisen’s shows, for example, air at the same time and are each heavily focused on the NFL.
Berry believes there could be a pathway to reunite with the Worldwide Leader.
“I like them a lot, they like me, and you never know where the future leads. It could lead nowhere; it could lead to nothing,” he said. “But I like them, and I root for them, but any time you are out on your own, and you’re looking for distribution, you’d be crazy not to call up ESPN and be like, ‘Hey, any interest here?'”

About Brendon Kleen
Brendon is an Editorial Lead at Awful Announcing overseeing digital content and special projects. He lives in Phoenix and has covered sports media for Awful Announcing since 2023.
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