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Stephen A. Smith Negotiating ESPN’s First $100M Deal, but ‘Issues to Be Resolved’

As FOS previously reported, Smith has been negotiating a blockbuster deal expected to pay him at least $20 million a year for five years.

Kirby Lee-Imagn Images

It was once axiomatic that nobody is bigger than the four letters at ESPN. But there are three letters that may put that platitude to rest: SAS.

Stephen A. Smith is making progress on a contract extension that could make him ESPN’s first-ever $100 million talent, sources tell Front Office Sports. But another source warned a long-term contract extension is not done—and there are “still issues to be resolved.” Either way, negotiations are expected to wrap up before Smith’s current deal expires next July.

As FOS previously reported, Smith has been negotiating a blockbuster deal expected to pay him at least $20 million a year for five years. His current annual compensation is $12 million. 

The Athletic’s Andrew Marchand reported Smith could add another year at $20 million per that would push his total compensation to $120 million over six years. Brian Steinberg of Variety reported Smith is close to a new agreement that would “involve creating a sort of ‘first-look’ agreement for Smith-backed concepts across Disney’s general-entertainment properties.” In June, John Ourand of Puck News reported Smith turned down ESPN’s initial offer of $18 million a year.

A $100 million–plus contract would set a new benchmark for ESPN talent. The Monday Night Football announcing duo of Troy Aikman and Joe Buck currently boast five-year deals worth $90 million ($18 million annually) and $75 million ($15 million), respectively. Meanwhile, Pat McAfee is collecting $85 million over five years ($17 million annually) to license his eponymous weekday show to ESPN. (He receives another cut via a separate talent-only contract with College GameDay.)

Tom Brady’s 10-year, $375 million deal ($37.5 million annually) with Fox Sports; Charles Barkley’s 10-year, $210 million deal with Warner Bros. Discovery; and Tony Romo’s 10-year, $180 million contract ($18 million) with CBS Sports are the three richest pacts in sportscasting.

There was speculation the move of Barkley’s Inside the NBA to ESPN might undercut Smith’s negotiating position. But both ESPN and Disney’s executives love the First Take’s star willingness to pitch in anytime, anywhere, from NBA Countdown to Monday Night Countdown—as well as his outsized consumer appeal at a time when consumers are cutting the cord with cable networks. 

Don’t forget Smith also wants to follow in the footsteps of his childhood idol Howard Cosell by becoming more involved in ESPN’s NFL coverage. Even with Sir Charles in the mix (albeit as a TNT employee), Smith remains ESPN’s biggest star. My sources believe a contract extension is a matter of when, not if.

As ESPN chairman Jimmy Pitaro told me during the network’s media day in Bristol, Conn., this fall: “Stephen’s very important to us. We have plenty of time here, so there’s no urgency. But my strong desire is to get a deal done with him.”

But Smith has become a very savvy businessman since ESPN dropped him in 2009. He has options. And timing is everything. NBC Sports and Amazon Prime Video are both hiring for their coverage of the NBA starting with the 2025–2026 season. As another source told me, both would “back up the Brink’s truck” to make Smith the face and voice of their hoops coverage. Smith’s owned and operated YouTube show is nearing one million subscribers. Throw in his other opportunities in late-night TV as well as mainstream news and acting, and Smith has leverage. 

As Smith told me at our live “Tuned In” event in September: “They have their vision—and I have mine. If it’s aligned, we’ll work it out. If it’s not, then decisions have to be made. I’m a big boy and I accept the fact that sometimes you don’t get what you want.”

ESPN and Smith’s representatives declined to comment.

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