The first time Donald Trump stepped on a presidential debate stage, on August 6, 2015, everyone thought they knew what would happen. Trump’s rise to the top of the Republican field still felt familiar then. He was the kind of candidate everyone understood to be a normal part of the GOP primary process: a populist outsider who rose on a wave of rhetorical flourish but would soon crash back to earth under the scrutiny a frontrunner faces from opponents on the debate stage and from the press in the spin room afterward. He was 2016’s Herman Cain or Michele Bachmann. Everyone was sure of it.
So as Trump walked to the center lectern at Cleveland’s Quicken Loans Arena, few entertained the thought that he would be back in this same building less than a year later, accepting the Republican party’s nomination. Instead, they believed he would embarrass himself, kicking off a slow shuffle to the bottom of the presidential pack, his nascent campaign relegated to the stuff of political trivia. That’s what happened after Bachmann said the HPV vaccine caused cervical cancer on stage following a debate, just one month and a day after her surprise win in the Ames straw poll. It’s what happened after Cain’s opponents, trailing the pizza baron in the polls ahead of the Iowa caucuses, stopped being nice and got real about his catchy but unvetted “9-9-9” tax plan at a debate in Nevada. The expectations among most pundits tuning in for Trump’s first debate against a field of experienced politicians was that it would happen again.
Instead, Trump turned the accepted concept of a good Republican primary debate performance on its head. At Hofstra University Monday night, he is set to once again share a debate stage with yet another experienced politician, before a television audience expected to be unprecedented in the history of American politics. This time, no one is sure what to expect.
Clinton’s campaign has reportedly prepared several distinct debate strategies for the Democratic nominee to have at the ready once the cameras switch on. Trump aides are bragging that their guy is ready to set the world on fire again. Pundits have thrown their hands in the air when it comes to the business of setting the odds.
Over the past month, we spoke to a half-dozen aides who prepped Republicans to debate Trump during the primaries and tried to strategize their way out of the aftermath of those debates. None said Trump is especially good at debating. But none said Clinton shouldn’t worry.
Trump did not do very well in that first debate by any conventional measure. He didn’t impress with his command of policy, nor did he leave anyone thinking he had commanded the stage. Many pundits declared John Kasich or Marco Rubio the winner. Trump faced tough questions from the panel of moderators and his responses left many observers saying the real winner was Fox News. Trump had a terrible next week in the press — he attacked debate moderator Megyn Kelly, saying she had “blood coming out of her wherever” following her string of pointed questions about his past statements about women. And that led to a string of condemnations from conservative leaders, culminating with the humiliation of Trump being disinvited from Erick Erickson’s “Red State Gathering” and Kelly being invited in his place.
But it didn’t matter. Trump blew through the remaining 11 debates in the primary calendar, grabbing headlines with quips like “Little Marco” (his nickname for Rubio) and “Lyin’ Ted” (as in Cruz.) He made faces, he boasted, he talked endlessly about his poll numbers. He never picked up a conventional debate win, but he won a bigger victory by redefining what it was to be in a presidential debate. Rubio, whom pundits had earlier praised for substance, showed just how much Trump had changed the game when, on stage in Detroit in March, he responded to one of Trump’s quips by calling the 236-pound frontrunner “Big Donald.”
The Detroit debate was widely seen as the last real stand for the professional politicians so sure Trump’s momentum would collapse that August night in Cleveland. A month after Little Marco took on Big Donald, Trump sewed up the nomination.
And so a strange version of the expectations game is now in full swing ahead of Monday’s debate. Campaigns often try to cast their candidate as the underdog, making it easier to explain away mistakes or to boost successes in post-debate punditry. Clinton’s campaign is executing this strategy. Trump’s is going another route.
Clinton aides, worried her experience means she faces higher expectations going into the debate, have spoken of the challenge of preparing to go up against a candidate who doesn’t play by any accepted political rules. They’ve gone so far as to say that Trump won the Republican primary debates, a revision of the general take at the time. And they’ve warned that moderators might not be reliable arbiters of the facts, preventing Clinton from winning on substance.
Trump and his supporters, by contrast, aren’t setting the bar low. Instead, they’re talking up the fact that Trump is eschewing traditional prep sessions (for the most part) and is relying on a team of advisers that reportedly includes former Fox News chief Roger Ailes. Trump’s lack of experience is an asset, his team says.
This leaves Clinton with just a few choices, the Republican strategists said. Each has its downside.
She can push Trump on the personal stuff in a bid to get him to say something unsavory. But that could lead to the kind of schoolyard brawl that left experienced, sharp-witted politicians like Bush and Cruz with silly, damaging nicknames that stuck in the minds of viewers.
Clinton can try to win the homework contest and bury Trump under policy knowledge. But GOP strategists said Trump effectively parried those moments in the primaries, at least with Republican voters, with tweetable lines like “We will have so much winning that you may get bored with the winning.”
Or Clinton can try to sit back in the hopes that Trump implodes under direct questioning from the moderator.
“You cannot prepare for [Trump] by trying to be intellectual and trying to talk substantively about the issues. That’s not going to work. He’s a street fighter — there are no tactics that he would not use in his debate,” said Armstrong Williams, a top adviser to Ben Carson who played the part of Trump during Carson’s debate prep sessions.
Carson endorsed Trump in March, but Williams was direct with his critiques of Trump’s debate strengths and weaknesses.
“If you can get under his skin, he can be very sensitive and he can wear his feelings on his sleeve. You know he’s very sensitive about whether he has big hands or not; he’s very sensitive when people ask, ‘What jobs have you really created?’; and he’s very sensitive when he tries to make the claim that everyone likes him,” Williams said. “He’s very into polls, but if you try to show him poll numbers that don’t reflect that, you can put him under the bus.”
Aides who prepped candidates to square off against Trump during the primary debates all gave some version of Armstrong’s take on the Republican nominee: Trump’s weakness is that he’ll risk doing long-term damage if it means scoring a point in the moment. He’ll lash out, saying something he might have to apologize for later. As the primaries wore on, aides said, they began prepping candidates more and more to needle Trump in the hopes that he would pop off, creating a viral moment like the infamous “Look at these hands. Are these small hands?” genital brag from Detroit.
That strategy proved a double-edged sword, though.
“He’s most dangerous when he feels like he’s losing and feels like someone has made a strong point,” said Michael Steel, a Republican political veteran who helped prep Jeb Bush for the debate stage. “When he needs to go back on the offensive, that’s when he says something inappropriate.”
Trump famously turned Bush into a punchline at the debates. Bush, a tested debater, policy expert and former Florida governor, tried to provoke Trump, but he was left sputtering. Bush scored points on Trump, and needled him into real flashes of anger, but it was easier for Trump’s attacks to stick. Bush wanted to engage Trump on policy details, but with as many as 10 other candidates on the stage, time didn’t allow for that kind of back-and-forth. Trump could fire off a zinger and move along.
Steel said Monday’s two-candidate format doesn’t afford Trump the same options.
“Trump is not actually a good debater, and this format, one on one, with a strong moderator, will be terrible for him,” he said.
Candidates who had prepared stacks of detailed policy documents or who had real experience in government tried to take on Trump over substance during the primary debates, often seeming to score points against a person who has admitted repeatedly that he’s not a policy wonk.
But one top strategist who served as a Trump stand-in for one of his top rivals in the Republican primary debate prep sessions said defeating Trump on policy points was a pyrrhic victory. The strategist requested anonymity in order to speak freely.
“He’s speaking the way voters think, and it may seem like the silliest thing you’ve ever heard, but voters react to it because it’s the way voters think about things — they don’t have all the deep policy details either,” the strategist said. “So he’s dangerous in that you could go into a debate and talk about all the intricacies of a bill that nobody cares about, nobody follows, and only you are the one talking about it. He’s actually saying what people think instead of what politicians say.”
Get out of the way
This last strategy was the one most Republicans employed early on. Looking back, the aides we spoke with did not recommend it.
“A lot of the times we’d think, ‘Let’s just let Trump be dumb and move on’ when he was setting the terms of the debate,” said the former stand-in for Trump. But that proved to be a decision that gave Trump more time to be Trump, something that worked quite well for him back when the audience was a Republican electorate.
But with a more general audience, outside observers say the format will be a star of the first debate. Ben Ginsburg, a Republican strategist who helped get Mitt Romney ready for his debates against President Obama in 2012, said a general election debate is necessarily different from a primary debate — in some ways that will play to Trump’s strengths, and in other ways to Clinton’s.
“The scope of issues that gets covered in a general election debate is much broader, so you have to prepare for that,” he said. “The second part of any debate prep is the performance art. There will be more cameras, higher production values, different things to think about.”
Anita Dunn, a former White House communications director and member of Obama’s debate prep team, said candidates heading into general election debates should expect coverage to focus either on huge gaffes or moments of tension. That bore out during the primaries when Trump often got was often given negative coverage of his undetailed policy knowledge while the bigger stories were about the insult wars he usually dominated.
“‘Candidates Exchange Barbs.’ ‘Candidates Trade Blows.’ I mean, that’s the coverage of debates when nobody makes a gaffe,” Dunn said, waving at hypothetical post-debate headlines. “People walk away with an impression, but it is those moments that people remember. And they kind of define what the debate was about.”
The biggest Republican advice to Clinton is to stop Trump from taking control of the debate, by any means necessary.
“In a debate, you can’t ignore that his style is effective,” the stand-in said. “So what we tried to do was set our own terms and make him respond to us.”