From Rotoworld to ESPN to NBC Sports, Matthew Berry is one of the most successful businessmen in the history of sports media.
Few analysts deserve more credit than Berry for bringing fantasy sports to the mainstream, and he leveraged the growth of fantasy into a lucrative career for himself. Over the past decade, that included his Fantasy Life brand. The platform began with his bestselling book of the same name and has blossomed into a popular fantasy sports and betting startup.
In a new interview on The Varsity podcast with John Ourand of Puck, Berry revisited his departure from ESPN — and revealed that he was at odds with the worldwide leader over Fantasy Life.
While ESPN initially supported Berry as an entrepreneur, when it came time for contract negotiations in 2022, the company changed course.
“My contract was coming up and ESPN came to me and said they liked me, wanted to bring me back, give me a raise, and a three-year extension,” Berry told Ourand. “But they said I’d have to get rid of Fantasy Life because they think it’s competitive. I told them I appreciate that they think I might be competitive, but that I respectfully disagree with that. Then I asked, ‘What’s more competitive—if I stay here and have this thing on the side, or if I go somewhere else and compete against you?'”
Berry raised $2 million for Fantasy Life in 2023 before striking a formal partnership with his new employers at NBC in 2024. That partnership added promotion for Fantasy Life to NBC Sports and Rotoworld platforms while adding certain insights from NBC to Fantasy Life’s subscriber tier.
Perhaps because ESPN Bet did not yet exist and the worldwide leader was late to the content party with gambling, ESPN did not have the same openings in which to plug Berry as NBC did. Either way, the growth of Berry’s startup made ESPN nervous.
“I love Jimmy [Pitaro], and I told him on the way out that I was leaving with hugs and handshakes, not a middle finger,” Berry said. “They had to make a decision for their business, and I had to make one for mine. And the decisions just weren’t the same. I decided to leave because Fantasy Life was that important to me—being able to control my own future and have something that I had an ownership stake in.”
As Berry noted, ESPN has changed course in other negotiations since his departure. From Pat McAfee to Stephen A. Smith to Shannon Sharpe to Jason Kelce, many of the top recent ESPN acquisitions also maintain large profiles outside the network.
Berry got no such chance, but it hardly stopped him as Fantasy Life and his audience at NBC grew.
About Brendon Kleen
Brendon is a Media Commentary staff writer at Awful Announcing. He has also covered basketball and sports business at Front Office Sports, SB Nation, Uproxx and more.