Let’s go to the tape: Clinton and Trump’s top 10 debate moments

Jerry Adler
·Senior Editor

One of the largest audiences in the history of presidential debates — perhaps the largest ever — is expected to watch when Hillary Clinton and Donald Trump face each other for the first time on the same stage. Clinton has a debate history that includes not just her appearances with Bernie Sanders in this cycle, but her epic confrontations with Barack Obama in 2008, all the way back to her campaign for United States senator in 2000. Trump built his winning primary campaign in large measure on his performance in a dozen debates against nine or more rivals since entering the race in 2015. Here are 10 key moments from this history that hint at how they will perform in New York Monday evening.

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Trump confronted by Megyn Kelly; Fox News Republican debate, Cleveland, Aug. 6, 2015: Donald Trump may have been expecting an easy time in the first Republican debate, hosted by Fox News. But Megyn Kelly came at him early and hard, memorably invoking the times “you’ve called women you don’t like fat pigs, dogs, slobs and disgusting animals.” “Only Rosie O’Donnell,” Trump interrupted. “No, it wasn’t,” Kelly responded, sparking an intermittent feud between the network and the candidate and giving the Clinton campaign one of its most potent talking points: Trump as a sexist bully.

Clinton lists her enemies; CNN Democratic debate, Las Vegas, Oct. 13, 2015: In a comment that presaged her characterization of some Trump supporters as “deplorables,” Hillary Clinton responded to a question about the enemies she is proudest to have made by naming “the NRA, health insurance companies, the drug companies, the Iranians … probably the Republicans.” Republicans were quick to seize on the remark as evidence of Clinton’s arrogant, us-versus-them attitude.

Trump boasts about his sexual endowment; Fox News Republican debate, Detroit, March 3, 2016: In an escalating round of taunts that began with Trump calling Marco Rubio “Little Marco,” the Florida senator mocked Trump, who is over six feet tall, for having “hands the size of someone who’s five foot two. And you know what they say about men with small hands.” On the debate stage, Trump retaliated: “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.”

Clinton invokes 9/11 to defend taking contributions from Wall Street; CBS News Democratic debate, Des Moines, Iowa, Nov. 14, 2015: Clinton’s rival, Sen. Bernie Sanders, attacked her over her ties to the financial industry. “Well, why do they make millions of dollars of campaign contributions?” Sanders asked rhetorically. “They expect to get something. Everybody knows that.” In a response that was widely viewed as off the point, or even insulting, Clinton invoked the attacks of 9/11 and suggested the contributions reflected the “whole lot of time and effort” she, as New York’s junior senator at the time, had put towards helping the financial district rebuild.

Trump defends Planned Parenthood; CNN Republican debate, Houston, Feb. 25, 2016: The unforgiving politics of abortion have confounded Trump several times during the campaign. In remarks that were seen by some as insufficiently hardline, he said he would cut off funding for Planned Parenthood — a long-sought goal of the Christian right — but defended their work on women’s health: “As far as Planned Parenthood is concerned, I’m pro-life, totally against abortion … but millions and millions of women, cervical cancer, breast cancer, are helped by Planned Parenthood. … I would defund it because I’m pro-life, but millions of women are helped by Planned Parenthood.

Clinton faces down Rep. Rick Lazio; WNED Senate debate, Buffalo, N.Y., Sept. 13, 2000: In her first political campaign, Clinton — still the first lady — faced upstate Republican congressman Rick Lazio. During an exchange over campaign spending, Lazio unexpectedly produced a “pledge” to renounce “soft money” and challenged Clinton to sign it. Stalking across the stage to face her at her podium, he shook off her offer to shake hands on an agreement, insisting, “I want your signature.” Lazio’s camp considered it a coup, but the next day most commentary cast it as a victory for Clinton — who managed to come off looking strong while winning sympathy for what many voters saw as Lazio’s bullying.

Trump says he’d bring back “a hell of a lot worse” than waterboarding; ABC News Republican debate, Manchester, N.H., Feb. 6, 2016: In response to a question about interrogating terror suspects, Trump staked out a position that was extreme even among his fellow Republicans. “In the Middle East, we have people chopping off the heads of Christians. … Not since medieval times have people seen what’s going on. I would bring back waterboarding and I’d bring back a hell of a lot worse than waterboarding.” He didn’t specify what he meant by “a hell of a lot worse,” but in speeches and other debates he endorsed the idea of killing the families of terrorists.

Obama calls Clinton “likable enough”; ABC News Democratic debate, Manchester, N.H., Jan. 5, 2008: The question of likability, which has dogged Clinton throughout this election, dates back at least to her first presidential run, when moderator Scott Spradling asked what she would say to voters who respect her qualifications but “seem to like Barack Obama more.” “Well, that hurts my feelings,” Clinton began, with an expression not unlike a teenager jilted by her prom date. “But I’ll try to go on. … He’s very likable, I agree with that. I don’t think I’m that bad…” Obama, presented with a priceless opportunity for chivalry, passed it up, interjecting — memorably, and in the opinion of many, cruelly, as Clinton shook her head wryly — “you’re likable enough, Hillary.”

Trump takes on Rubio and Cruz at the same time; CNN Republican debate, Houston, Feb. 25, 2016: If you had to choose one moment when the Republican primary seemed to go off the rails, it might have been the exchange when Trump, positioned between Marco Rubio and Ted Cruz, took on both of them simultaneously. “This guy’s a choke artist,” Trump bellowed, gesturing at Rubio, and, turning to Cruz, said, “and this guy’s a liar!” As moderator Wolf Blitzer tried vainly to bring Gov. John Kasich into the conversation, Ben Carson could be heard off-camera plaintively pleading: “Can somebody attack me, please?”

Clinton opens up about her feelings on being the object of political attacks; CNN Democratic debate, Austin, Texas, Feb. 21, 2008: Asked to identify “the moment that tested you the most,” Clinton acknowledged living through “some crises and some challenging moments,” but left them to the imagination — and recollection — of the audience. She spoke about seeing wounded service members at a military hospital, and added: “You know, the hits I’ve taken in life are nothing compared to what goes on every single day in the lives of people across our country. And I resolved at a very young age that I’d been blessed and that I was called by my faith and by my upbringing to do what I could to give others the same opportunities and blessings that I took for granted. That’s what gets me up in the morning. That’s what motivates me in this campaign.”