It’s 2024 and Rosie O’Donnell Is Sparring With Bill O’Reilly on Trump


Comedian and former talk show juggernaut Rosie O’Donnell was willing to lay down some serious cash (for most people) with a bet that Donald Trump would be found guilty on any charges brought against him—but conservative commentator and Trump hype man Bill O’Reilly chickened out of an opposing bet against her Wednesday night during a cable news segment that felt like a throwback to another era.

O’Donnell and O’Reilly were guests on the ex-CNN host Chris Cuomo’s NewsNation show when they got into a verbal sparring match about Trump’s impact on the country. “Democracy is on trial,” O’Donnell said on the show this week. “We have to get everyone back together again in some way,” she continued, “Without this, we’re nothing as a nation.”

O’Reilly jumped in to defend Trump, saying “Rosie, with all due respect, you’re not gonna be successful saying that democracy is on trial and anybody who supports Donald Trump is a fascist,” he said. “Those people are gonna reject you because there’s a lot more to it than you are presenting.”

“Donald Trump presided over the country for four years and there was no attack on democracy until January 6th,” O’Reilly continued, “And that was a large mistake that he made, I don’t believe that he was behind it. I think that if that trial ever gets up, he’ll be acquitted. It’s too much exculpatory evidence.”

O’Donnell shot back, “I totally disagree with you that he didn’t have anything to do with the insurrection, that he didn’t instigate it, plan it, demand it of his fans, because he did, Bill.” O’Reilly apparently then felt the need to up the ante to prove his point and offered O'Donnell a $10,000 bet that Trump wouldn’t be convicted of insurrection charges.

“We'll see in court what is presented, and if you are correct, I will take a $10,000 bet right now with you to your favorite charity or mine that Donald Trump will not be convicted of insurrection, because he’s not charged with it,” he said. After Cuomo called O’Reilly a “cheap-o” for putting a bet on the table for charges that aren’t even in play, O’Donnell offered O’Reilly a new one.

“$10,000 that he is found guilty—not of [insurrection]—the other charges,” O’Donnell said. “Anything he is charged with, I agree he will be guilty.” O’Reilly offered only an awkward pause and a “We’ll see,” after which he was goaded by Cuomo, who asked “You take the bet?” O’Reilly promptly changed the subject.

“I’m not really fearful for our democracy,” O’Reilly said as O’Donnell rolled her eyes, “My freedom was not impeded one iota during the Trump administration.

“I don’t know any broadcasters’ freedom who was,” he said, invoking O’Donnell’s former show. “You still have The View on every day pounding Trump into pudding, nothing happens,” he said, adding that “all the working people” he knows were “better off” under Trump and there were no “economic consequences” to Trump’s presidency. “I really don’t know what the hyperbole is,” he concluded.

Said O’Donnell in response, “That’s bull!”

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