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EARLY in 2007, Barack Obama met Hillary Clinton at a candidates forum on health care in Las Vegas in one of their first encounters on a debate-like stage, in what would become one of the longest nominating battles in presidential campaign history.
When he returned to Chicago, he was glum.
“Hillary looked like a president up there, and I didn’t,” he told me.
As the senior strategist for Senator Obama, I spent the better part of two years thinking about how to deal with Hillary Clinton. Fluent in policy and crisp in delivery, Mrs. Clinton dished out all that Mr. Obama could handle in the 26 debates of that marathon campaign. We won the race, but she came out on top in many of those encounters, including one in New Hampshire that may have cost us a critical early primary victory.
Mrs. Clinton is an accomplished debater, and there is no question that she upped my candidate’s game and her own over time. But she will be facing an entirely different kind of opponent on Monday night.
There is no whiff of the Oxford Union about Donald Trump. He barreled through a spate of primary debates as an improvisational performer, long on chutzpah and borscht belt put-downs but short on facts. Yet by making it to this stage, the reality show star has ridden the unconventional to the cusp of the presidency.
Mr. Trump’s bludgeoning style and boundless bluster have frustrated opponents, moderators and media analysts all season. But what elite commentators have dismissed as boorishness has, to many alienated voters, signified strength, authenticity and, crucially, a willingness to defy “political correctness.”
Throughout the campaign, Mr. Trump has rewritten the rules and played a game that’s entirely his own. It is the key reason Monday’s audience is expected to be one of the largest for any show in television history. The sheer element of unpredictability and audacity Mr. Trump brings is the attraction.
It may be that he will turn in a muted performance on Monday, convinced that he needs to show presidential temperament and some mastery of substance to woo swing voters who dislike Mrs. Clinton but doubt Mr. Trump’s fitness for the job. If Mr. Trump chooses to ride the horse that got him here, however, Mrs. Clinton will confront a showman bent on turning the event into less of a debate and more of a spectacle.
As the world knows, Mr. Trump’s chief debate tactic to date is getting under the skin of his opponents by identifying perceived vulnerabilities, appending pejorative descriptors, and then making them stick.
When he gleefully attacked primary opponents on the debate stage, they generally reacted in one of two ways. Some sputtered, looking as if they had been hit in the face with a pie. Others, most notably Senator Marco Rubio, responded in kind, and looked bad doing it.
Mrs. Clinton, who has high unfavorable ratings of her own, will have to find the right tone if Mr. Trump fires at close range the kind of gibes he has hurled from afar at her honesty, her tenure as secretary of state, her vote to authorize the use of force in Iraq — even her treatment of her husband’s infidelities and the women involved.
She will be armed with an encyclopedic knowledge of Mr. Trump’s own significant vulnerabilities but, in past debates, Mr. Trump generally has benefited from nasty, personal volleys with his opponents, so she will have to decide when to defend, when to attack and when to rise above.
Instead of engaging Mr. Trump frontally in an ugly contest of insults, the best course for Mrs. Clinton may be to navigate around him. Even as she strikes contrasts, she should take her case directly to the camera and the American people, referring to Mr. Trump without engaging him.
But what if the other Trump appears on Monday? Though it’s tough for a brawler to show restraint for 90 minutes, it might make strategic sense for him to try and strike a reassuringly thoughtful and temperate pose.
This version of Mr. Trump would create a different challenge for Mrs. Clinton: She cannot allow her opponent to use the campaign’s largest audience to rehabilitate himself with voters who doubt his fitness for the office. She must hold him accountable for his most provocative comments and his utter lack of substance.
In past debates and interviews, Mr. Trump has demonstrated an appalling, almost defiant, lack of knowledge, and these debates, with long segments devoted to specific topics, will demand depth beyond oversimplified answers. Secret plans to defeat the Islamic State, for example, will not pass muster.
Mrs. Clinton cannot count on the moderators to corral Mr. Trump or perform the role of fact-checker. She will have to do this herself, choosing when and where to challenge Mr. Trump’s logic and facts without belaboring the tactic or coming off as the obnoxious smartest kid in the class.
One of Mr. Trump’s chief assets is his self-cultivated image as a business titan. Managing the economy is one of the few categories in which he has consistently outpolled Mrs. Clinton. (Mitt Romney enjoyed this same presumption over President Obama in pre-election polling.)
Mr. Trump surely will brandish his business credentials and present himself as the only “job creator” on the stage. But in doing so, he will open himself up to a strong counterattack about dubious business tactics, bankruptcies and schemes like Trump University. The Clinton team will know going in that questioning Mr. Trump’s wealth and business success is a hot button, the only one that seems to unsettle him.
Yet if some wavering voters will be watching to see if Mr. Trump appears to be a plausible president, others will tune in to discover if Mrs. Clinton, who has struggled with questions of trustworthiness, can speak in an open and authentic way that connects with them. They will be looking for what, beyond personal ambition, motivates her and where, beyond the policies of President Obama, she aims to lead.
The well-crafted Democratic convention in July, a high-water mark for Mrs. Clinton, offered a strategic road map to how best to position herself, Mr. Trump and the choice between them.
If she holds true to that successful template, she will pitch herself as a champion for economic fairness and Mr. Trump as a populist poseur, whose actual practices and policies belie his claim to advocacy for working people.
She will emphasize the sure-handedness and discretion needed in a commander in chief and contrast that with Mr. Trump’s troubling penchant for loose talk and bellicose language.
Without pretense about the challenges Americans face, she will offer a more optimistic vision of the future than Mr. Trump’s relentlessly dystopian portrait of a country on the brink — the audacity of no hope. She will embrace diversity as a strength, in contrast to his past slights on immigrants, Muslims, women and people with disabilities.
Finally, she will stress the need to work together to solve the nation’s problems and mock Mr. Trump’s oft-stated declaration that he will single-handedly cure America’s ills — on Day 1. Both liberals and conservatives bridle at this autocratic vision.
In the end, presidential debates are less a trial of fact than a televised final exam for the most exacting job on the planet. They offer Americans a window into how each of these candidates would deal with excruciating pressure. They are measured in revealing moments. Will the candidates react with grace, humor and unflappability, or with anger and uncertainty?
Mrs. Clinton’s history has been to rise to these occasions. She calmed unsettled Democrats last fall with her confident and steadfast 11-hour-long appearance before the congressional committee on Benghazi and a series of strong primary debate performances with a dogged challenger, Senator Bernie Sanders.
If she can handle the asymmetric challenge of the unorthodox Mr. Trump, she will have taken a big step forward to solidifying her hold on the race, but more important, she will have shown that she can handle pretty much anything.
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