Stephen A. Smith? Mark Cuban? More and more Democrats are looking for an outsider

The Democratic race to succeed President Trump in 2028 could be shaping up to be an outsider's race.

Down in the dumps after their devastating loss to Trump — the ultimate outsider — in November, Democrats increasingly are saying they must consider all options as they chart the way forward. That means looking beyond candidates to people who don't fit the traditional bill, they say.

Billionaire business mogul Mark Cuban? Let’s take a look.

What about sports commentator Stephen A. Smith? I’m interested, say Democratic consultants and strategists.

Their sharp eyes are also considering politicians who don’t look like politicians. Sen. John Fetterman (D-Pa.)? Definitely a possibility.

“In modern political history, there's never been a time that's more favorable for someone not of the system to rise in Democratic politics,” said Joel Payne, a veteran Democratic strategist who added that these potential candidates “have a bigger lane now more than ever.”

Since November, Democrats have been engaging in an autopsy of what led to a second term for Trump. In the months since, more and more strategists in the party say it must break from cyclical thinking where the next traditional politician in line steps up as the “candidate in waiting.”

It’s a sharp turn from the last two cycles, in which Democrats nominated party veterans.

Democrats put up Hillary Clinton in 2016 because at the time it seemed like it was “her turn,” even as the country was leaning toward a more populist stance. And while former President Biden won in 2020, many Democrats blame him for bringing the party down and not being able to land punches against Trump.

When Biden stepped down as the nominee in July 2024, the Democrats quickly coalesced around the obvious candidate in waiting, then-Vice President Kamala Harris.

As Democrats watch Trump reshape the federal government, they are looking for new answers, and not just in those who would fit a more traditional mold, such as Govs. Josh Shapiro of Pennsylvania, Gretchen Whitmer of Michigan and Gavin Newsom of California; former Transportation Secretary Pete Buttigieg; and Harris.

Democrats have always bandied about names like Oprah or former first lady Michelle Obama in their moments of desperation. What’s different this time is that there’s a very real element to those discussions.

“I think we need more and varied voices charting the path forward, listening to what voters have to say,” said Democratic strategist Anthony Coley. “I think we have to be open enough and humble enough to listen to people who are not traditional candidates when voters are saying they want to disrupt the status quo.”

Even the so-called outsiders say it’s time for the Democratic Party to shake things up.

“I understand why they have interest in me,” Cuban told The Hill in an email exchange. “Name recognition, understands business, AI and crypto. Those are all in vogue right now.”

Cuban flirted with presidential prospects in 2020 but ultimately decided against it after his family disapproved. Late last month, he told a crowd he wasn’t interested in a White House bid in 2028. “Hell no,” he said at a Principles First convention in Washington, when asked if his name could be on the ballot. “It’s not going to happen.”

In the email exchange with The Hill, Cuban homed in on where Democrats have gone wrong: "The real issue is communication.”

“In the world today, the [algorithm] wags the dog. Donald Trump has become a master of flooding the zone with nonstop 'stuff,'" Cuban said. “Not all of it has to go viral, but if enough does, it fills the feed on every social media platform. And to make matters worse, the Dems and left-leaning media spend all their time responding to it."

Cuban said Democrats “have to realize they can’t be so responsive to Trump with every little thing. They can’t hate everything. That didn’t work before. It won’t work now. They have to be proactive, in volume, and make the Republicans react to them in a way that makes voters realize the Dems are moving forward something that benefits the American people.”

In recent days, Democratic Party operatives have also considered others including former New York Gov. Andrew Cuomo, who just announced a mayoral bid in New York City this week. Insiders say while Cuomo has a blemished track record amid a rash of sexual harassment allegations, it’s a different time. Voters, they say, want someone who can take a swing at Republicans.

“If we're not uncomfortable then we're not being creative enough,” said Democratic strategist Jamal Simmons. “The same normal things won't work in this era because it's not a normal time.”

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