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Technicians set up the stage for the presidential debate between Democratic presidential candidate Hillary Clinton and Republican presidential candidate Donald Trump at Hofstra University in Hempstead, N.Y., Sunday, Sept. 25, 2016.Patrick Semansky/The Associated Press

Each considers it essential. Each considers it the leading event of the 2016 race for the White House. Each has much to gain – and even more to lose. Monday night's first presidential debate is the most anticipated showdown since the first one, pitting Senator John Kennedy against Vice-President Richard Nixon more than a half-century ago, an event that was one of the most-viewed broadcasts of the new television age.

"There was enormous attention to that first debate, partly because it was such a new thing," said Sander Vanocur, the former NBC newsman who is the only person involved in the 1960 debate still alive. "We didn't have a lot of preparation. The debate was a big deal but we didn't make a big deal about it." Everyone is making a big deal about Monday's, the first of three confrontations between former secretary of state Hillary Clinton and businessman Donald Trump.

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That's because, more than any of the 31 previous presidential debates, this session is a classic example of asymmetrical warfare, a conflict between two candidates whose styles and strategies could not be more different. Like an asymmetric military conflict, this one involves an established figure tangling with an insurgent.

Anything could happen in such a confrontation, where assets become disadvantages and skills become liabilities.

This debate – organized by a bipartisan commission – comes at a vital juncture in the campaign, when Ms. Clinton's long-held lead is being cut by a Trump surge – itself a classic element of asymmetrical warfare. "The establishment tried to push Trump out but wasn't able to do it," three-time presidential candidate Patrick Buchanan, himself an insurgent, said in an interview. "It ain't over til it's over. Right now Trump has the momentum and she has had some serious problems."

Here are the essential elements of this exercise in asymmetry.

She prepares, he doesn't

Ms. Clinton is the classic campus bookworm, a style honed at Wellesley and at Yale Law, where she was a star student and where her attention to her studies was legendary. That diligence paid off for her as a young law professor, as an establishment lawyer, as a senator and as secretary of state.

Now she faces her most high-profile challenge, and it comes against a candidate who luxuriates in his contempt for traditional preparation and for all of the elite credentials, mannerisms and outlooks that Ms. Clinton possesses.

Mr. Trump rarely takes briefings and seldom retreats for reflection or preparation. The result is a fresh and free-wheeling style that won him admirers but which now faces its most high-stakes test "There's always an abundance of information on any topic, but in order to be effective in a limited-time public debate you have to choose your arguments and your supporting materials carefully," said Thomas Foley, the president of Mt. Aloysius College in Cresson, Pa., and the former debate coach at Bates College and Yale University. "Trump is banking on the fact that his crowd loves the free-verse he provides. The problem is that most of the people who will tune in are actually interested in the issues."

She has mastery, he doesn't

All those hours in briefings, all those pages in those briefing notebooks, all that reading of the fine print, whether of legislation or international agreements – that has either given Ms. Clinton the confidence to plow through the debate or clogged her head. Nancy Reagan complained that her husband's aides had stuffed his mind with statistics and arguments and that once he got on the stage with Walter Mondale in 1984 he became flummoxed.

For Mr. Trump, the situation is completely opposite. He's survived, and thrived, with limited traditional background.

"Trump filibustered his time in the small amount of time he was given in multicandidate debates in the primary," said Brendan Nyhan, a Dartmouth College political scientist. "There will be a lot more time in this debate. The problem for him is that he runs out of things to say after 15 or 20 seconds. There may be two minutes in each question segment, and then there may be followups. He has to have material to fill that time."

She's politically experienced, he's not

On paper, Ms. Clinton has a remarkable background, far deeper and broader than any presidential contender since Senator Robert Dole in 1976 or, perhaps Vice-President George H. W. Bush in 1988. But this is a peculiar presidential contest, where experience is degraded – and where the patois of politics might be a burden.

"It's important to know the issues but more important to talk to people in a way people understand and appreciate – and sometimes those speaking in political terms can turn people off," said GOP Senator Rob Portman of Ohio, who played Barack Obama in mock training debates for both Senator John McCain in 2008 and former governor Mitt Romney in 2012. "Political people don't talk the way normal people talk about things, and that can be a disadvantage."

She's scripted, he's spontaneous

Ms. Clinton has many skills, but none that she has mastered so completed as one of the essentials of politics: Stay on message. But sometimes she's so devotedly and completely on-message that she sounds inauthentic. That is not a Trump problem, even though he probably repeats his sound-bite lines ("Make America great again," or "We're going to win," or "It's a disaster") far more often than Ms. Clinton.

There are advantages and dangers in this element of presidential debates. Candidates know what they want to say – and are especially determined to say it. Then again, that determination can often turn a debater into an automaton. Striking the balance is the key – and the challenge.

"A successful presidential debater has to be both scripted and spontaneous," said Mr. Mondale, a veteran of both vice-presidential and presidential debates. "You are going to get some tough questions where the stylized response just won't work. If people think you're memorizing an answer, you're dead."

The world's leading expert in the perils of memorized ripostes is Senator Marco Rubio of Florida. He repeated his scripted lines attacking Mr. Obama four times, prompting Governor Chris Christie of New Jersey, a rival GOP candidate, to ridicule him. It was at once one of the most memorable and most devastating moments of American presidential debate history. Memo to the candidates: Memorize the lesson here.

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