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Trump Tells Stephen A. Smith He Would Beat Barack Obama Easily, Calls Him Highly Overrated

Trump called the former president a 'divider' during a White House sit down on Stephen A.'s Straight Shooter podcast, days after Republicans took a beating in the midterms.

Dee Dee Henderson by Dee Dee Henderson
November 13, 2026
in Political News
Reading Time: 3 mins read
Trump Obama matchup as Donald Trump and Barack Obama appear side by side

Donald Trump and Barack Obama

Donald Trump told Stephen A. Smith he would “easily” win a hypothetical Trump Obama matchup, calling former President Barack Obama “highly overrated” in a White House interview released Thursday.

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The conversation aired on Smith’s Straight Shooter with Stephen A podcast and covered a range of issues following the Republican Party’s losses in the midterm elections. At one point, Smith floated a scenario where Trump and Obama could both run for a third term and go head to head.

Neither man can actually do that. The 22nd Amendment to the Constitution limits a person to being elected president twice, which rules out both of them. Trump still answered like the race was on the calendar.

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“I got many more votes than he got, and I got many more votes in the states,” Trump said, adding that he holds the all time vote records in big states like Texas and Florida.

Smith pressed him directly. “Are you saying you’d beat Obama?”

“Yeah, I think I’d beat him easily,” Trump said.

Smith’s face said everything, and Trump noticed. He followed up with the line that is now making the rounds: “I think he’s highly overrated.”

When Smith asked him to explain, Trump said Obama was not a good president and was more of “a divider.” He then claimed that he himself “brings people together” through shared success. For a man whose Truth Social posts regularly attack Democrats, judges, reporters and members of his own party, the Trump Obama matchup answer did not land the way he may have hoped with Smith, who looked visibly unconvinced.

On the vote count, Trump’s raw totals in 2020 and 2024 did top the 69.5 million votes Obama won in 2008. The country also has millions more voters now than it did then, so the raw numbers alone do not settle much.

The timing of the shot at Obama stands out. Obama spent the midterm season on the campaign trail for Democrats, and several of the candidates he rallied for won their Senate races, including Sherrod Brown in Ohio and Abdul El-Sayed in Michigan. Trump’s party lost ground across the map, and Smith later said Trump was “immovable” when it came to accepting any blame for those losses.

The interview also had a moment aimed at Smith himself. Trump asked whether Smith would ever run for office, something Smith already ruled out earlier this year. Trump offered some advice anyway. “I would keep your life the way it is. You know what? You’ll find it very nasty if you do,” he said.

The two have a complicated history. Smith has had dinner with Trump and now landed a sit down at the White House, but Trump has also publicly blasted him in the past, calling him an “arrogant fool” and “a low IQ individual” as their back and forth played out.

Obama has not publicly responded to Trump’s comments.

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Dee Dee Henderson
Dee Dee Henderson is a Poli Alert journalist covering national politics, elections and the policies that hit closest to home for Black communities, from voting rights and the economy to the courts. She reports the facts first and isn't afraid to say what they mean, and her commentary pieces are clearly labeled as opinion. Her midterm coverage breaks down deadlines, ballot measures and the races that will decide who holds power in Washington.
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Dee Dee Henderson

Dee Dee Henderson

Dee Dee Henderson is a Poli Alert journalist covering national politics, elections and the policies that hit closest to home for Black communities, from voting rights and the economy to the courts. She reports the facts first and isn't afraid to say what they mean, and her commentary pieces are clearly labeled as opinion. Her midterm coverage breaks down deadlines, ballot measures and the races that will decide who holds power in Washington.

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