Here Are the 5 Wildest Moments from Donald Trump’s Debating Career

Say what you will about Donald Trump, the man is quotable — and some of his best work has come during debates. In honor (or dread) of his taking the stage again on Thursday night, we’ve compiled some of the craziest moments to come out of his previous appearances at such events.

“ONLY ROSIE O’DONNELL”

Trump debut was a doozy, and his most memorable moment came when he was asked the toughest question of the night by moderator Megyn Kelly.

“You’ve called women you don’t like fat pigs, dogs, slobs, and disgusting animals,” observed Kelly. “Your Twitter account –”

That’s when she was cut off by the candidate who declared, with the slightest trace of a smirk on his face, “Only Rosie O’Donnell!” to thunderous applause. Kelly tried to correct the record once the crowd settled down, but it was too late. Trump had easily deflected a seemingly devastating line of attack on him and bent voters’ perception of reality to his benefit.

“Frankly, what I say — and oftentimes it’s fun, it’s kidding, we have a good time — what I say is what I say,” he declared.

“LOOK AT THESE HANDS!”

As the 2016 GOP primary entered its home stretch, things got particularly personal between Trump and Senator Marco Rubio (R-FL). While the latter is now reportedly a finalist in the former’s veepstakes, their feud produced one of Trump’s most memorable moments back in 2016.

On the campaign trail, Rubio made fun of Trump for the size of his hands — and the associated implications for another part of his body.

“He’s like 6’2’’, which is why I don’t understand why his hands are the size of someone who’s 5’2’’. Have you seen his hands? And you know what they say about men with small hands?” Rubio asked in one particularly devilish moment.

This was a rumor Trump could not possibly abide, and so he addressed it at the next debate.

“He hit my hands. Nobody has ever hit my hands, I’ve never heard of this one,” insisted Trump. “Look at those hands. Are they small hands? And he referred to my hands, ‘If they’re small, something else must be small.’ I guarantee you there’s no problem, I guarantee it!”

“BILL CLINTON IS ABUSIVE TO WOMEN”

The second debate of the 2016 general election cycle occurred shortly after the infamous Access Hollywood tape — on which Trump boasted about grabbing women “by the pussy” — leaked. Trump apologized for what he said while characterizing it as “locker room talk,” but he also went nuclear on his opponent, Hillary Clinton, inviting her husband Bill Clinton’s various accusers to the debate.

“That was locker room talk. I’m not proud of it. I am a person who has great respect for people, for my family, for the people of this country and certainly I am not proud of it, but that was something that happened,” acknowledged Trump before dropping the hammer:

If you look at Bill Clinton, far worse. Mine are words and his was action. His words, what he has done to women. There’s never been anybody in the history of politics in this nation that has been so abusive to women. So you can say any way you want to say it, but Bill Clinton is abusive to women. Hillary Clinton attacked those same women, and attacked them viciously, four of them here tonight.

One of the women, who is a wonderful woman at 12-years-old was raped. At 12. Her client, she represented, got him off and she is seen laughing on two occasions laughing at the girl who was raped. Kathy Shelton, that young woman, is here with us tonight. So don’t tell me about words. I am, absolutely, I apologize for those words, but it is things that people say, but what President Clinton did, he was impeached, he lost his license to practice law, he had to pay an $850,000 fine to one of the women. Paula Jones who is also here tonight.

And I will tell you that when Hillary brings up a point like that and she talks about words that I said 11 years ago, I think it’s disgraceful and I think she should be ashamed of herself, if you want to know the truth.

“YOU’D BE IN JAIL”

Also at his second debate with Hillary Clinton in October 2016, Trump dropped a one-liner for the ages.

After Clinton submitted that “it’s just awfully good that someone with the temperament of Donald Trump is not in charge of the law in our country,” Trump deadpanned, “Because you’d be in jail” in reference to Clinton’s mishandling of classified information and to roars of approval from the audience.

The quip followed chants of “Lock Her Up!” at various Trump rallies and certainly represented an unfortunate first in presidential debate history. But it was also an effective, pithy retort that highlighted one of Clinton’s key vulnerabilities.

And the moderators’ complaints about the audience’s reaction only served to reinforce Trump’s argument that Clinton had gotten away with something she shouldn’t have.

“STAND BACK AND STAND BY”

At his first presidential debate with Joe Biden back in 2020, moderator Chris Wallace asked Trump if he was willing “to condemn white supremacists and militia groups and to say that they need to stand down and not add to the violence in a number of these cities as we saw in Kenosha and as we’ve seen in Portland.”

“Sure, I’m willing to do that,” replied Trump.

“Are you prepared specifically to do it? Well go ahead, sir,” shot back Wallace.

Trump went on to condemn “left-wing” violence and seemed not to quite understand what it was Wallace was looking for. Eventually, Biden jumped in to ask Trump to condemn the Proud Boys, an alt-right group with a penchant for showing up at tense protests and other such events.

“Proud Boys, stand back and stand by,” instructed Trump. “But I’ll tell you what, I’ll tell you what: somebody’s got to do something about Antifa and the left because this is not a right-wing problem this is a left-wing. This is a left-wing problem.”

Wallace’s less than clear line of questioning and the crosstalk obscured the exchange. But the way Trump put it opened him up to fair criticism that he had instructed an extremist organization to “stand by” and be ready to act.

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