By 
Jim Newell
Successfully debating Donald Trump is the hardest thing 
that 
should be an easy thing in our world today, right up there with beating 
Donald Trump in an election with adult voters. In debate after debate after 
debate during the Republican primaries, Trump showed little understanding of or 
curiosity about public policy, instigated childish fights with his rivals, and 
disappeared from the conversation altogether when it bored him. He skipped one 
debate because he didn’t like Fox News’ sass. In another that he 
did 
attend, he bragged about the size of his penis. Never forget that he bragged 
about the size of his penis in a debate among candidates vying for the United 
States presidency. And never forget that, either in spite or because of all 
this, he won the Republican nomination for said presidency and is now polling 
neck-and-neck with his Democratic competitor, Hillary Clinton.
During the primaries Trump was able to get away with being his unvarnished 
self. In creating his primary plurality, he hardened for himself a national 
majority in opposition to him. The gains he’s seen in polling during September 
have come from both Clinton missteps and a more disciplined operation under new 
Trump campaign manager Kellyanne Conway, who has tamed her candidate’s feral 
impulses at the margins. There are even murmurs that Trump is 
preparing 
for Monday’s first debate at Hofstra University, which might have less to 
do with his domestication than with the fact that he is about to go in front of 
the biggest television audience he’s ever had. What keeps the Clinton campaign 
awake at night must be the possibility of Trump passing through this first 
debate with a calm and poise for which he is not known. The Trump campaign’s 
hope is to trick people, white-collar white people in particular, into believing 
that he is indeed calm and poised. Once Trump is onstage and under duress, 
though, he will be tempted to revert to his nature. Clinton’s goal will be to 
induce such behavior—to coax out the real Trump, the one who “won” in the 
primary by losing the majority of the country. Here’s how she can do that.
Ask him to explain pretty much anything.
The large Republican primary field didn’t just help Trump by allowing him to 
cruise to early victories with relatively modest pluralities. It also helped him 
in the minute-to-minute unfolding of the early debates. He could get in his 
insults against Jeb Bush or Rand Paul or some other foil, and then, as the 
conversation—as it occasionally did—ventured into more substantive policy 
grounds, he could go into hiding for tens of minutes at a time as, say, Paul and 
Chris Christie argued about surveillance programs or medical marijuana. The 
stage will be smaller Monday night, as Trump competes in the first one-on-one 
presidential debate of his life. There will be no hiding.
It’s not necessarily in Clinton’s interest to turn this into a patronizing 
quiz show. Voters don’t cast their ballots based on which candidates best trill 
the rhotic consonants in foreign leaders’ names. But there are things that 
people expect their presidents to know, and on this count Trump tripped up a few 
times during the primary debates.
In the Dec. 15 debate held in Las Vegas, CNN guest questioner Hugh Hewitt 
asked Trump which element of the aging nuclear triad he felt was most urgently 
in 
need 
of an upgrade. Trump’s response was a jumble of nonsense about Iraq and 
Syria that made clear he had never heard the term, which refers to land-, air-, 
or sea-based systems for delivering nuclear weapons. That’s not great. But it’s 
deeper than terminology: It was clear that he had never considered the question 
of nuclear arsenal maintenance. He did, however, say that, “I think, for me, 
nuclear is just the power, the devastation, is very important to me.” Indeed, 
big bomb go boom.
Trump is running strongly against the Trans-Pacific Partnership. (Hillary 
Clinton claims to be against TPP, too, 
though 
no one really believes her.) When asked for even modest details of the trade 
pact, though, Trump tends to stumble. In the 
Nov. 
10 debate, Trump went on about how “It’s a deal that was designed for China 
to come in, as they always do, through the back door, and totally take advantage 
of everyone.” For all of the trade deal’s opacity and complexity, it is indeed 
not “designed” to allow China to do that. It is 
designed to 
corner China into reforming its economy. Rand Paul chimed in after Trump’s spiel 
to point out that China is not a signatory to the deal, and Trump had little to 
say in response. The next day Trump and his team retrofitted their version of 
the exchange to make it sound as if he knew exactly what he was saying and what 
he meant. This 
explanation, 
too, was lacking.
Clinton doesn’t need Trump to name the presidents and prime ministers of 
foreign countries. What she—or the moderators—could do, though, is ask him to 
explain the details of any of the policy proposals other people have written up 
on his behalf. How many weeks of paid leave are offered in Trump’s child care 
plans? Who would and wouldn’t be covered? Trump could be asked the cost of 
either his tax or education plan. Even better: What 
are his tax and 
education plans?
One of the most effective versions of this model in the primary was when Sen. 
Marco Rubio, during the Feb. 25 debate, asked Trump to explain his health care 
plan. This is where Trump went on about “the lines,” referring to selling 
insurance across state lines, but had little else to offer beyond 
repetition.
Clinton doesn’t just need to ask him about his own plans. She could ask him 
to explain 
anything. How does Medicaid work and how would he change it? 
What does he dislike most about the Iranian nuclear deal? What’s the latest from 
Syria? Don’t wander too far in the weeds, but try to find some way to get him to 
move past the few superficialities he’ll have memorized. Remember: 
Trump 
does not know what he’s talking about. 
Ever. 
This fact gets obscured from time to time whenever we start talking about 
Trump pivots and message discipline and the like, as if the problem simply were 
a lack of grace. And we should be careful to avoid the fallacy so common on the 
left that politics is about knowing more stuff than the other guy. But the 
simple truth is
 that Trump does not understand the basic grammar of the 
job he’s seeking.
Get him to say something incredibly sexist.
An observation: Hillary Clinton has faced sexist criticisms in her career. 
You may have noticed this.
A twin observation: Donald Trump has dished out a lot 
of sexism in his career. You may have noticed this, too. One dynamic of the 
debate, then, is whether Trump will be able to stop himself from making some 
outward expression of his sexism—a remark, a gesture, anything.
There was one woman in the field of 16 competitors dispatched by Trump en 
route to the nomination.
Though Carly Fiorina posed little threat, Trump was 
unable to control himself against her. He was unable, as 
reported 
by Rolling Stone, to prevent himself from saying about Fiorina: 
“
Look at that face! Would anyone 
vote for that? Can you 
imagine that, the face of our next 
president?!” This was something that 
he had to say.
Trump did not acquit himself well when that quote was brought up in the 
(interminably long) Sept. 16 debate at the Ronald Reagan Presidential Library in 
California. Trump had claimed that by “face,” he meant her 
persona. 
Moderator Jake Tapper asked Fiorina to respond to it all. With great poise, she 
said, “I think women all over this country heard very clearly what Mr. Trump 
said,” to roaring applause. Trump, to groans, replied: “I think she’s got a 
beautiful face, and I think she’s a beautiful woman.”
Fiorina 
did 
shoot up in the polls after this debate, before the usual combination 
of additional scrutiny and unsustainable media oxygen sent her back down to the 
realm of also-rans.
Hillary Clinton has experience in one-on-one debates with male counterparts 
who express 
fatally 
boorish behavior. It will be the test of a lifetime for Trump to make it 
through one debate without patronizing her similarly; he needs to, though, if 
he’s to recover some of his numbers among suburban college-educated women, the 
traditionally Republican demographic that Trump has bled from his wherevers. 
Don’t let him. Mention some of his sexist remarks. Maybe he’ll keep it together 
during the debate, and wait until the 
next day to say 
something 
terrible.
Draw out his childishness.
Trump needs more voters coming out of the debate thinking that he’s a 
properly matured adult, rather than a child. One common trait among children is 
their inability to manage their passing rages. The proper response here is not 
for Clinton to respond in kind. She’s not a natural heckler, and when people who 
aren’t natural hecklers try to meet Trump on his level, 
they get mauled. Trump is 
the only candidate who can pull off his brand of childishness. That’s not a 
compliment.
Sen. Ted Cruz, the best debater in the Republican primary field, demonstrated 
the best way of managing Trump’s puerility. It was the 
Mar. 
3 debate. Cruz prodded Trump by bringing up a piece of unwelcome 
information, in this case the pending lawsuit against Trump University, and how 
he might be on the stand for a “fraud trial” during the general election 
campaign. This had the instant effect of agitating Trump into sputtering 
interruption. 
Cruz 
was ready. 
CRUZ: And with Hillary Clinton ... 
TRUMP: Give me a break. 
CRUZ: ... pointing out that he supported her four times in her 
presidential race. 
TRUMP: It’s a minor civil case. 
CRUZ: Donald, learn not to interrupt. It’s not complicated. 
TRUMP: There are many, many civil cases. 
CRUZ: Count to 10, Donald. Count to 10. 
TRUMP: Give me a break. 
CRUZ: Count to 10. 
This shut him up in the moment, which made him even 
angrier. When it 
was finally his time to speak, he barked about how he was much higher in the 
polls. Trump’s polling position in the general election has sharply improved 
since Labor Day, but hardly into bragging territory. He’ll be without that 
crutch this time.
Don’t do this stuff.
Don’t think for a second that Hillary can’t blow this. Oh, she can.
Imagine a debate in which Trump keeps his cool. In which he treats Hillary 
Clinton respectfully and barely even looks at her. In her efforts to provoke 
him, she comes off as the desperate one. She does the thing where she addresses 
this generation’s electorate with the last generation’s panders, like 
invoking 
9/11 to defend her lucrative dives into the Wall Street fundraising 
pool.
Her internal algorithm for divining the proper positions has a tendency to 
output jibberish—the meeping nonposition of the career pol. Recall her waffling 
in the 2007 debate about whether she would support drivers’ licenses for 
undocumented immigrants.
No, she finally answered. 
Two 
weeks later.
Clinton hasn’t gotten much better in this respect. She 
still can’t 
quite nail down concise answers for either her private email server or what 
safeguards she put in place against foreign influence-peddling through the 
Clinton Foundation during her time at State.
She’s not a bad debater. She’s far better in this environment than she is in 
big auditoriums, trying to rile up the crowds at her rallies. But she’s the sort 
of non-natural politician who, when she needs to force something, comes off very 
obviously as someone who is forcing something.
What Clinton needs to remember is that there’s no pressure here. Only some 
100 million people will be watching, and the only thing she could blow is the 
presidential election. If she loses the election, no big deal. America will just 
be turning control of the world over to a lunatic, ending liberal democracy’s 
solid post-war run at seven decades. She might faint or make one tremendous, 
highly replayable gaffe. But again, the only consequence there would be the end 
of the West. It’s fine. It’s fine. Everything’s fine.