Stephen A Smith Credit: Nightcap on YouTube

The Stephen A Smith empire keeps growing.

Amid talk of a potential 2028 presidential run and the final steps of a contract negotiation with ESPN, Smith continues to find a larger profile in political commentary. That’s just how the First Take host planned it when he launched The Stephen A. Smith Show and his Straight Shooter Media company. However, despite Smith’s obvious knack for getting his point across, he believes he has been held back from translating that talent to other fields throughout his career.

Now, having built First Take into a juggernaut and earned the trust of his Disney bosses, Smith is finally off the leash.

Discussing that newfound freedom on Nightcap with Shannon Sharpe and Chad Johnson this week in New Orleans, Smith described feeling “neutralized” by management at ESPN and other bosses — and how that doubt fuels him today.

“I was neutralized to some degree by my employers,” Smith said. “First the Philadelphia Inquirer, then CNN, then FOX Sports, then ESPN.”

Smith believes athletes like Sharpe and Johnson benefit as media personalities because they enter the space with a greater level of freedom than journalists. Yes, athletes have the lived experience in sports to pull from, but Smith explained that executives shy away from containing athletes. In contrast, they gladly constrain their more traditional hosts and analysts.

Once Smith saw athletes growing their media profiles and openly wading into whatever topics they wanted to, he wanted what they had. ESPN gave him the green light to launch his own show, so long as it didn’t conflict with his roles at the network.

“I said, ‘I don’t want a sports show,'” Smith said. “And when I told them [I would cover] pop culture and entertainment and politics, they were like, ‘Go ahead.’ Because nobody thought that I would resonate, because they didn’t know.”

The latest comments from Smith suggest the future of The Stephen A. Smith Show and his appearances outside ESPN are the final issues to be broached as he finalizes a new contract to remain at the Worldwide Leader. It would be hard to imagine Smith backing down from hosting the show, given that he has grown it to more than 1 million subscribers on YouTube and created a niche for himself in new spaces. For someone who has achieved so much within sports, the chip on Smith’s shoulder as an outsider in politics and pop culture is real.

To be fair to ESPN, they restrain all talent from publicly sharing political opinions. If anything, Smith has gone beyond just about any talent in the company’s history by building his platform to discuss politics.

At the same time, as Smith entertains a run for political office, ESPN needs to be sure what the future might hold. The Athletic recently reported that ESPN allows Smith to appear on outlets like Fox News or Bill Maher’s HBO show because it is outside the bounds of his role as a sports analyst for the network. But a contract negotiation provides the opportunity for Disney to tighten up the terms of that agreement as Smith pushes the boundaries of his profile in media and beyond.

If Smith has felt limited by his bosses in the past, he has clearly enjoyed the past couple of years of free reign. Yet it’s hard to imagine that Disney would be thrilled to have Smith running for president while he gives sports analysis on First Take each morning.

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.