Stephen A. Smith on The Stephen A. Smith Show Photo credit: The Stephen A. Smith Show

The most anticipated sports media free agency of 2024 is here, as Stephen A. Smith and ESPN are engaged in negotiations on a new contract. According to James Andrew Miller, a longtime insider covering the network, Smith could get upward of $20 million in his next move. However, his primary management may not come from ESPN but instead from William Morris Endeavor, the agency that represents him.

In an appearance on SI Media with Jimmy Traina released Thursday, Miller detailed the latest on Smith’s contract talks and how WME could craft a cocktail of jobs for Smith that ultimately pays him more handsomely than Disney and allows him to leave the worldwide leader.

“Stephen A.’s deal is coming up. In fact, I think there have been preliminary talks already that have started. He’s looking for a big, big number,” Miller reported. “And I also feel, given the content world, he doesn’t even have to have another offer from one entity for that big number. I think what ESPN is up against is the possibility that WME could go out and create an architecture where Stephen A. has a podcast, a this, a deal with this, a deal with that, whatever, and at the end of the day, it’s $20 million a year.”

Smith currently produces a podcast in partnership with iHeartMedia and frequently appears on Fox News to discuss politics. Over the past year or more, he has guested on seemingly every podcast in sports, entertainment, and business. Smith produced a documentary for ESPN on the history of sports debate and has teased future narrative television projects and an interest in acting.

It all begs the question: Does Smith need ESPN anymore to make money and have a platform?

“I do believe there are enough possibilities … that Stephen A. can get outside of ESPN and even outside an exclusive deal with another network that could make him very happy and very rich,” Miller said.

Still, from a financial standpoint, Miller posited that ESPN could find enough change in the couch cushions to make it worth Smith’s while. The extra flexibility, Miller said, could come from ESPN losing UFC rights. Miller projected those rights could go to Netflix when they are up in 2025.

If WME is able to strike deals with a news network, audio company, and Hollywood distributor, Smith could have his cake and eat it, too. He clearly loves the status and platform he gets on First Take, which he also executive produces, but the point here is that he does not need First Take to have a voice and make a ton of money.

[SI Media with Jimmy Traina]

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.