

The 2024 presidential election left plenty of political dust behind. But few moments were as unexpected-or entertaining-as when Stephen A. Smith’s name popped up in political speculation. The catalyst? Mark Cuban, the billionaire entrepreneur who had just wiped his Twitter clean of pro-Kamala Harris endorsements. He was quietly repositioning himself on the political spectrum. What followed was a wild media ride. Two of America’s most recognizable non-politicians became headline-makers in the national political conversation.
It’s 2025, and politics feels less like policy debates and more like a group chat gone viral. Few know how to break the internet like Stephen A. Smith. With one cryptic tweet—“2028? @jonstewart”—Smith teased a possible future run for president. He even tagged Jon Stewart. Was it serious? Or classic Smith mischief?
Behind the viral moments, Smith’s political journey is more complex. He openly regrets voting for Kamala Harris in 2024. Smith criticized the Democratic Party’s focus on identity politics. He believes it often overshadows the economic and social issues affecting everyday Americans. On Real Time with Bill Maher, he admitted, “I felt like a fool for backing Harris.” He also said the Democratic Party needs a “purge” before he would consider running under its banner.
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2028, @jonstewart? pic.twitter.com/U0xBFozA3x
— Stephen A Smith (@stephenasmith) May 17, 2025
Smith calls himself “fiscally conservative, socially liberal, and a registered independent.” He holds a centrist stance that doesn’t fit neatly with either major party. This ambivalence reflects a wider disillusionment with the polarized political scene. He sees the system as flawed and resistant to real change.
Yet whispers persist. Elected officials and billionaire donors have privately nudged him about a 2028 run. When former President Donald Trump said, “I’d love to see Stephen A. run,” the rumor mill kicked into overdrive. Whether serious or a viral tease, Smith’s knack for turning a few words into headlines is undeniable.
From Courtside to Capitol? Stephen A. Smith’s Political Playbook with Mark Cuban
Stephen A. Smith isn’t exactly rushing into politics, and that’s a bit surprising given how fast things keep changing out there. But he’s not figuring it out alone. His longtime buddy, Mark Cuban, gives us a peek behind the scenes at what’s really going on with this reluctant political figure. Together, they’re creating a new kind of political player — smart with media, bold with opinions, and not tied down by the usual party drama. Think of them as mixing pop culture and politics like a perfectly timed alley-oop pass.
At the same time, Mark Cuban has been shifting his own political stance. He used to loudly support Kamala Harris — praising her for pushing an “opportunity economy” that would help small businesses grow. The timing was telling. Right after the election, Cuban congratulated Donald Trump and Elon Musk publicly, showing he’s more about practical thinking than sticking to one party.
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Talking about Stephen A.’s political path, “I don’t think he wants to be POTUS,” Mark Cuban, a friend of Mr. Smith’s, said in an email, “but I know he is loving the discussion.”
Mark Cuban hasn’t held back when it comes to calling out political dysfunction. In a February 2025 TIME article, he took aim at the Democrats for what he described as strategic failures, while also critiquing Donald Trump for prioritizing PR over policy. For Cuban, it’s less about party lines and more about accountability—he’s consistently stressed the importance of clear communication over blind party loyalty.
Neither Mark Cuban nor Stephen A. Smith has officially announced a run for office, but both have grabbed the spotlight with their charm, smart moves, and perfect timing.
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This whole situation says a lot about how politics looks after 2024 — people are tired of the usual party drama and want fresh voices. Celebrities like Stephen A. Smith, Mark Cuban, and even Donald Trump have blurred the lines between entertainment and politics, shaping how voters think through viral moments instead of traditional campaigns.
Today, headlines can come from just about anywhere — even a basketball analyst and a billionaire entrepreneur. And as long as the political show keeps going, Mark Cuban and Stephen A. Smith will be there, stirring the pot and keeping us all wondering what’s next.
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