BRISTOL, Conn. — Stephen A. Smith is ready for some football.

The face of ESPN grew up in Hollis, Queens, idolizing Howard Cosell. As ESPN kicks off its new season of Monday Night Football tonight with the Jets vs. 49ers, keep this in mind: Smith told me he wants to follow in Cosell’s footsteps by more directly covering the NFL.

The featured commentator of First Take talks about the NFL every day on his top-rated weekday program; a show like Monday Night Countdown would simply be a bigger platform. Not to mention his recent headline-making interview with Cowboys owner Jerry Jones on his eponymous YouTube show/podcast.

“I don’t want to insult the legacy of the great Howard Cosell, who’s somebody that I idolized. But that’s what I want to do,” Smith told me during ESPN’s recent media day here. “When I think about the NFL, I’m not talking about being in the booth with Troy Aikman and Joe Buck. You don’t mess with that chemistry; you leave that alone. But I’m unapologetic about what I want. I would love to be a part of Monday Night Football. I would love to work with [Monday Night Countdown’s new cast including] Jason Kelce and Scott Van Pelt and Ryan Clark and my man Marcus Spears. I mean, two of those guys are on First Take every week.”

New Territory

Besides scratching a personal career itch, costarring on ESPN’s Monday Night Countdown would be a savvy business move. As he negotiates for a contract extension, Smith is aiming to become the highest-paid on-air talent at ESPN, surpassing Aikman’s $18 million-per-year payout. If he scores a long-term deal worth $20 million a year or more, he could become ESPN’s first $100 million talent.

ESPN pays $2.7 billion annually for Monday Night Football, and the NFL is its most important rights partner. Not to mention, ESPN is gearing up to aggressively cover its first Super Bowl in 2027 “like it’s never been covered before,” according to president of content Burke Magnus. (As part of its last media-rights deal, Disney’s ESPN scored the rights to its first two Super Bowls after the 2026 and 2030 seasons.)

For those who believe Smith’s résumé is too NBA-centric for ESPN’s NFL shoulder programming, I’d point to his growing voice on boxing and mixed martial arts. Not to mention his outspoken opinions on politics, pop culture, business, and social issues. He covers a wide range of topics.

“Of course, I believe that I can do it,” Smith told Front Office Sports. “When you think about Howard Cosell and what he meant to the business, do I believe I have the potential to mean nearly as much? Yes, I do. So that’s my opinion. It doesn’t mean that opinion is shared by others. We’ll find out …”

I asked ESPN chairman Jimmy Pitaro about Smith, whose current deal expires in July 2025. Pitaro told me you can put a Stephen A. contract extension at the top of his wish list.

“Let’s be clear: 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,” said Pitaro. “There are various options we’re looking at right now. He’s got great representation. We’re in conversations right now. One thing that Stephen and I agree on is that we’re not going to negotiate in public. So I have to honor that. But just know, Mike, that I want to get this done, and we want to get this done. He’s incredibly important to us. I’ve never once asked Stephen to do anything where he’s said “no.” He’s one of the hardest-working people I’ve ever met in my life. I feel like he represents ESPN really well. I do believe people tune in for Stephen. That’s important. He’s a needle-mover. So my strong desire is to stay in business with Stephen.”

[Want to hear directly from Magnus and Smith? Front Office Sports’ inaugural Tuned In sports media summit will come to life Tuesday, Sept. 10 as a one-day event in New York City, and they’re two of the featured guests. It’s not too late; you can register now.]

As talents like Smith, Pat McAfee, and Shannon Sharpe of ESPN, and Colin Cowherd of Fox Sports morph into entrepreneurs with their own podcasts/production companies, they’re gaining more clout in contract negotiations. 

Smith has talked about eventually moving to late-night television (possibly succeeding ABC’s Jimmy Kimmel), acting, or politics. The author of the best-selling memoir, Straight Shooter, could also focus on his own YouTube show and production company, Mr. SAS Inc., which has multiple projects in development in Hollywood.

The good news for Smith is that ESPN parent Disney could tailor a sports and entertainment package that would keep him at the Mouse House. I asked Smith about just such a deal. He liked the idea as his reps discuss his contract with Pitaro and Magnus.

“I don’t know what the future holds. I know that I love doing First Take. They know that. I know that I’m willing to still do the NBA. They know that. I know that I want to do the NFL. They know that. But they also know I have my own digital platform, with my podcast, that I own and operate 100%. And I have no intentions of changing that. And that I give a lot of social commentary. That involves social, political, and beyond. That’s not going to change, either. Wherever that takes us, that takes us. Hopefully, it will take us to a point where we can reach an accord—and reach an agreement.”

A Dominant Tenure

Smith’s First Take has reigned as the No. 1 show in the weekday 10 a.m. to noon ET time slot for 12 years. If you think success has softened his competitive edge, you should have seen him bristle when I asked about First Take dominating Skip Bayless’s rival Undisputed. (The competition got so lopsided that FS1 recently dumped Bayless.)

Smith declared the so-called “competition” between him and his former partner was more media creation than reality. 

“One of the biggest misnomers that was ever made is that there was competition in the 10 o’clock hour. At 10 a.m., when Shannon Sharpe was with Skip Bayless for six and a half years, we did over 1,600 shows against them. They came within half of our ratings, twice. Two times. None of you ever wrote that. Not one time,” he admonished the press. “Now, I obviously wasn’t going to say that. Because obviously Skip Bayless and I have a long relationship. Shannon is here on board now. He’s my teammate; he’s done an electrifying job for the show, and I’m incredibly appreciative of it. But we’ve dominated at 10 a.m. since 2012. Every day, every week, every month, and every year for 12 years now and counting. So this notion that suddenly, we’ve won, and the competition has finally been defeated, and, ‘Wow, it was such a long, arduous battle.’ It’s just not true.”

Smith doesn’t intend on slowing down anytime soon. After a serious bout with COVID-19, he went on a fitness kick and has lost 40 pounds.

What about The Facility, FS1’s new entry vs. First Take? Good luck. Smith expressed his zero-sum goal when it comes to competitors: “My objective is annihilation. Whoever goes up against me, I’m taking down. That’s what I’m trying to do every day, every week, every month of every year.”

When the best thing about Tom Brady’s TV debut is a slickly produced commercial, Fox Sports has a problem.

Brady was shaky during his broadcast debut of Sunday’s Cowboys vs. Browns game. His cadence was choppy. He confused offensive and defensive players, spoke in clichés, and seemed a step behind technically. 

I’m not blaming Brady. The usually terrific Fox team had an off day. Play-by-play announcer Kevin Burkhardt confused a Cowboys assistant with head coach Mike McCarthy. Producers mixed up Dallas placekicker Brandon Aubrey with punter Bryan Anger. The disconnect was on display when rules analyst Mike Pereira, (after forgetting to turn on his mic) awkwardly left Tom Terrific hanging on a fist bump. 

Bright Spots

Brady and Burkhardt had their moments. They seemed to be having fun when the Cowboys toyed with having Aubrey try a record 71-yard field goal. The seven-time Super Bowl winner loosened up in the second half and showed his old fire. Even while down by more than three TDs, it was important for the Browns to play hard in front of their home crowd, he noted. “Are we going to lay down—or are we going to go out there and fight? That’s what I want to see from Cleveland.” One of his best moments came when he circled the threat posed by Micah Parsons just before the pass rusher tipped a pass leading to an interception.

When Erin Andrews told a story about Cowboys defensive coordinator Mike Zimmer cursing out star players, Brady flashed his sense of humor. “I played with a coach who wasn’t afraid to cuss out his players, either,” joked the former Patriots quarterback about former coach Bill Belichick.

The Athletic’s Dianna Russini, host of the new Scoop City podcast, saw a lot of promise in Brady’s debut. As Russini told me Sunday night: “Brady is really likable. He’s thoughtful and takes a beat to explain what he is looking at. Sure, there are minor things but all that comes with reps. I was impressed, but not surprised. He’s going to be incredible by the time we get to Halloween.”

Another broadcaster who requested anonymity had this to say about Brady: “Like a rookie with high expectations and big salary, it’s hard to reach that level everyone wants. Personally, I’d like to see more enthusiasm, humor, & personality. He’s lacking right now BUT I’ve heard how dedicated he is to this & have no doubt by mid-season, he’ll more than hit his stride.”

If anything, the meticulous Brady may have over-prepared. In my first “Tuned In” newsletter, I reported he and Burkhardt cycled through a full season of practice games. He sought advice from peers, Troy Aikman among them.

Brady was at his most comfortable during the fourth quarter. He should be fine after an adjustment period. But he needs to start listening to his own voice rather than others’ and be more critical of players and coaches. Fox signed Brady to a record 10-year, $375 million deal, but there’s no need to panic on their end, either. Brady is too smart, too talented to struggle for long.

If things go south, Fox still has Emmy-winning analyst Greg Olsen, who called a great game Sunday with new partner Joe Davis. (In fact, the overwhelming sentiment from people I follow was for Fox to put Olsen back on the No. 1 team.) Fox should let Brady be Brady. He’ll figure out how to succeed in his new career just as he did his last one.