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What to Watch for During Monday Night's Clinton-Trump Mudfight

After spending months insulting each other, Hillary Clinton and Donald Trump will finally have their first face-to-face showdown on Monday in Long Island.
September 26, 2016, 12:00am
The stage being prepared for the debate between Hillary Clinton and Donald Trump. (AP Photo/Patrick Semansky)​

Monday night is, weirdly, a pivotal night in US history. For the first time in a campaign that has lasted for 16 long months, Donald Trump and Hillary Clinton will take the stage at Hofstra University in Hempstead, New York, for 90 minutes of honest-to-God debate. After months of trading insults at rallies, in campaign ads, and on Twitter, we will get to see them go face-to-face. Who handles who could determine the election, and, if you want to get hyperbolic—it's undeniably in fashion—the future of American democracy.


During the Republican primary debates, Trump amplified the reality show tendencies these events naturally had, bullying the other candidates and making the race all about him. He gave America what we so viciously crave: entertainment. In the other corner, we have Clinton, the first female major party nominee for the White House, who proved her own skill in a series of primary debates against Bernie Sanders where she effectively scored points and convinced Democratic voters that she was what a president looked like.

The reason this will likely be the most-watched debate in history is that the two candidates have such contrasting styles. Can Trump's bravado and bluster hold up for an hour and a half? Will he be able to talk policy specifics, or, at least, convince voters he knows what he's talking about? Will Clinton allow any of Trump's insults to get under her skin? Can she finally do what no Republican has done before, and expose Trump for being a small-minded bigot and bully?

Here's a breakdown of what to expect from Clinton, Trump, and moderator Lester Holt.

Hillary Clinton

It's been maddening to watch Clinton's campaign lately. Her campaign bungled the release of a pneumonia diagnosis, which fed right into two of Trump's criticisms: the candidate's trustworthiness and allegations of her secretly poor health. She followed that up with her "basket of deplorables" comment that allowed Trump to paint her as effectively dismissing a quarter of Americans as "irredeemable" racists. Then polls showed that her support among millennials and Hispanics is short of where Barack Obama was in '08 and '12. As Trump began to gain serious ground both nationally and in key states, you could almost hear liberals everywhere bookmarking long-term Airbnbs in Alberta.

But as has been the case for months, the pendulum soon swung back the other way. The Obamas, Sanders, and liberal hero Elizabeth Warren stumped on her behalf, and the press became focused on Trump's whole birther thing, the dodginess of his foundation, and his failure to release his tax returns.


Clinton has plenty of experience debating in both crowds and one-on-one, stretching back to the 2008 Democratic primary. Back then (as she does now), she touted her experience and policy knowledge; Obama pursued the by-now-familiar tactic of painting her as a politician who changed her views as the winds shifted.

But sometimes, this wonkiness works—in debates against Sanders this year, Clinton made the Vermont senator come off tongue-tied on complex issues like gun control and foreign policy while she stayed confident and calm. Her greatest debate weakness remains her habit of seeming slippery. This election, one of Clinton's worst moments was her response to Sanders's claim that she was too cozy with Wall Street. In response, she offered a platitude about being a New York senator on 9/11 as the reason she was close to the banks.

Last week, Democrats shared some advice for Clinton with Politico, the sum of which was let Trump lose all by himself. The best example of Clinton capitalizing on her opponent's mistakes is her famous exchange with Republican Rick Lazio in the 2000 New York Senate debate. Lazio, a sort of proto-Trump, OD'ed on macho-ism when he walked over to Clinton's podium and aggressively demanded she sign a pledge against soft money in politics. All Clinton had to do was stand there and smirk to herself as Lazio's campaign self-immolated.

For all their heft and hype, debates are generally remembered for one or two moments like that—if Clinton keeps her composure and lets Trump take the low road, she might emerge on the other side with a viral clip that's remembered until November. If Clinton's vulnerabilities are obvious, so is her mission in the debate: Don't fuck up.

Donald Trump

It's easy to reduce Trump to caricature: a blabbermouth who is his own worst enemy and says whatever insult comes into his head. But in the Republican debates he had a few incredibly savvy turns. In the first one, he bragged about buying politicians, in the process offering one of the most effective, easy-to-digest distillations of corporate control in Washington. Tellingly, no one onstage could rebut him. Later in the campaign, he easily gutted Ted Cruz when the latter used "New York values" as an insult.

But this isn't the primaries anymore. Trump has never faced off against a single opponent for 90 minutes, and in those early debates, he was speaking to, and about, Republicans. On Monday, Trump will have tens of millions of eyeballs on him—most of whom do not agree with some of his staple policies. So, Trump will need to make sense of those positions, draw stark lines between himself and Clinton, and introduce himself to Americans who may not really know what he's all about.


Expect him to lean hard on his "America First" message and repeat his claim that Clinton is "the chief emissary for globalism." Trump's whole message is that he can keep the US safe: safe from immigrants, safe from terrorism, safe from the unpredictable shifts of the global economy. According to him, Clinton doesn't actually care about ordinary people and is more concerned with helping foreigners, the DC elite, and corporations. But for this to be effective, he'll have to seem like the sort of man who really could keep Americans safe—not a nutjob, in other words, and not a name-caller.

"If she treats me with respect," Trump told Bill O'Reilly recently, "I'll treat her with respect." But it's hard to believe that will happen, especially given the fact that the former reality TV star created a mini controversy by joking (?) about inviting Bill Clinton's former mistress Gennifer Flowers to the debate. Not to mention, Roger Ailes, the former CEO of FOX news, has been prepping Trump for the big showdown. Ailes's old network made Clinton conspiracies a cottage industry, obsessing over everything from Whitewater to Benghazi. If he's whispering into Trump's ear, mud-slinging should be expected.

Lester Holt

The third character in this two-person play is the media, which by and large has struggled to cover Trump. Initially, the press portrayed him as a curiosity. And now that he's for real, there remain a host of questions about how to deal with him. Does the focus on his many, many controversies drive a cycle of mutual dependency? Is it appropriate to cover him the same way you do Clinton? How much should interviewers challenge Trump when he says something that isn't true?

On Monday, the media will be represented by Lester Holt, NBC News's soft-spoken, modest anchor. It didn't take long for Trump to question Holt's legitimacy as a moderator, calling him a Democrat—even though it was later revealed that Holt, in fact, is a registered Republican, a rather tidy summary of Trump's habits of finger-pointing and inaccuracy.

Even when moderators fade into the background, they have enormous power to shape the content of debates. All eyes are on Holt now: How deep will he dig into issues like Trump's tax returns and charitable spending, or Clinton's never-ending email scandal? Challenging Trump on this stuff would earn plenty of accolades from the left, but voters also need to know where the candidates differ on topics from ISIS to immigration to infrastructure. Left to their own devices, Clinton and Trump could snipe at each other's failings all night—which is why they can't be left to their own devices. So if this freak show needs anything, it's a ringmaster.

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