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Inside the Final Hours of Debate Prep for Hillary Clinton and Donald Trump

7 minute read

After more than a year of wall-to-wall campaigning, the outcome of the 2016 election could hinge on 90 unpredictable minutes Monday night in Hempstead, N.Y.

The first presidential debate between Hillary Clinton and Donald Trump is expected to be the most watched in history, with perhaps 100 million viewers tuning in for a showdown with the power to upend an increasingly close race. Given the reach of social media, every mistake or charged moment at Hofstra University will be amplified for the remaining five weeks before Election Day.

The clash comes at a crucial moment for Clinton. The Democrat’s summer lead has dwindled in recent weeks amid fresh scrutiny of her private email server, a bout with pneumonia and more disciplined performances by her opponent. Polling averages now show Clinton with a narrow national advantage. Surveys of crucial battleground states — including Ohio, Florida, Nevada and North Carolina — are within the margin of error, while Trump has pulled ahead in Iowa and shaved Clinton’s cushion in Virginia, Michigan and Wisconsin.

Read More: Donald Trump Called Debate Moderator Lester Holt a Democrat. He’s Actually a Republican.

Clinton still boasts far more paths to the required 270 electoral votes. She enjoys an advantage in on-the-ground organizing in battleground states and a virtual monopoly over the airwaves. But her campaign’s failure to put Trump away has Democrats fretting. Trump is a canny media manipulator, and Monday night on Long Island offers him the best forum this fall to channel his celebrity into political credibility by projecting a presidential bearing, just as early voting gets under way.

Despite radically different approaches, both candidates have proved to be formidable opponents. A veteran debater, Clinton is known for preparation, precision and a firm grasp of policy. She often got the better of Barack Obama during their 2008 primaries, and muscle memory helped get her back into fighting condition during her many clashes against Vermont Senator Bernie Sanders this year.

Trump, on the other hand, is the ultimate wildcard. His performances during the Republican debates this year were effectively erratic, peppered with personal insults, flamboyant boasts and often flat-out falsehoods. Once, he was even a no-show. It’s an approach his GOP opponents often found hard to counter, and part of the challenge was the mystery of which Trump would show up. Sometimes he slung mud; sometimes he tried to float above the fray. His stumbles did little to dissuade his fervent supporters.

A Year on the Campaign Trail With Donald Trump

Republican presidential candidate Donald Trump speaks to an overflow crowd during a campaign rally, Tuesday, Sept. 6, 2016, in Greenville, N.C.
Republican presidential candidate Donald Trump speaks to an overflow crowd during a campaign rally in Greenville, N.C., on Sept. 6, 2016.Evan Vucci—AP
A Secret Service agent waits for the arrival of Republican presidential candidate Donald Trump to a campaign rally, Tuesday, Sept. 13, 2016, in Clive, Iowa.
A Secret Service agent waits for the arrival of Republican presidential candidate Donald Trump to a campaign rally, Tuesday, Sept. 13, 2016, in Clive, Iowa. Evan Vucci—AP
An airport worker races to prepare the stairs as the plane of Republican presidential candidate Donald Trump arrives for a campaign rally on Sept. 17, 2016, in Colorado Springs, Colo.
An airport worker races to prepare the stairs as the plane of Republican presidential candidate Donald Trump arrives for a campaign rally on Sept. 17, 2016, in Colorado Springs, Colo.Evan Vucci—AP
Republican presidential candidate Donald Trump talks with press, Sept. 5, 2016, aboard his campaign plane while flying over Ohio, as Vice presidential candidate Gov. Mike Pence, R-Ind., left, looks on.
Republican presidential candidate Donald Trump talks with press, Sept. 5, 2016, aboard his campaign plane while flying over Ohio, as Vice presidential candidate Gov. Mike Pence, R-Ind., left, looks on. Evan Vucci—AP
Republican presidential candidate Donald Trump speaks during a campaign rally at High Point University, Sept. 20, 2016, in High Point, N.C.
Republican presidential candidate Donald Trump speaks during a campaign rally at High Point University, Sept. 20, 2016, in High Point, N.C. Evan Vucci—AP
Republican presidential candidate Donald Trump holds a pair of babies as he works the rope line during a campaign rally, July 29, 2016, in Colorado Springs, Colo.
Republican presidential candidate Donald Trump holds a pair of babies as he works the rope line during a campaign rally, July 29, 2016, in Colorado Springs, Colo. Evan Vucci—AP
A Miami police officer stands guard during a campaign event with Republican presidential candidate Donald Trump at the James L. Knight Center, Sept. 16, 2016, in Miami.
A Miami police officer stands guard during a campaign event with Republican presidential candidate Donald Trump at the James L. Knight Center, Sept. 16, 2016, in Miami. Evan Vucci—AP
Republican presidential candidate Donald Trump shakes hands with supporters after landing at a site of the Republican National Convention, July 20, 2016, in Cleveland.
Republican presidential candidate Donald Trump shakes hands with supporters after landing at a site of the Republican National Convention, July 20, 2016, in Cleveland.Evan Vucci—AP
Republican presidential candidate Donald Trump speaks during a campaign town hall at Ocean Center, Aug. 3, 2016, in Daytona Beach, Fla.
Republican presidential candidate Donald Trump speaks during a campaign town hall at Ocean Center, Aug. 3, 2016, in Daytona Beach, Fla.Evan Vucci—AP
Robert Einspahr, of Denver, lights a cigarette as he waits for the arrival Republican presidential candidate Donald Trump to a campaign rally, Sept. 17, 2016, in Colorado Springs, Colo.
Robert Einspahr, of Denver, lights a cigarette as he waits for the arrival Republican presidential candidate Donald Trump to a campaign rally, Sept. 17, 2016, in Colorado Springs, Colo. Evan Vucci—AP
Nathan Paikai, of Honolulu, waits for the arrival of Republican presidential candidate Donald Trump at a reception with friends and family following the Republican National Convention, July 22, 2016, in Cleveland.
Nathan Paikai, of Honolulu, waits for the arrival of Republican presidential candidate Donald Trump at a reception with friends and family following the Republican National Convention, July 22, 2016, in Cleveland.Evan Vucci—AP
Republican presidential candidate Donald Trump speaks during a campaign rally at Germain Arena, Sept. 19, 2016, in Ft. Myers, Fla.
Republican presidential candidate Donald Trump speaks during a campaign rally at Germain Arena, Sept. 19, 2016, in Ft. Myers, Fla. Evan Vucci—AP
Notes sit on the lectern after Republican presidential candidate Donald Trump spoke during a campaign rally at Cumberland Valley High School, Aug. 1, 2016, in Mechanicsburg, Pa.
Notes sit on the lectern after Republican presidential candidate Donald Trump spoke during a campaign rally at Cumberland Valley High School, Aug. 1, 2016, in Mechanicsburg, Pa. Evan Vucci—AP
Donald Trump
Kendra Wright, of Auburn, Wash., listens to Republican presidential candidate Donald Trump speak during a campaign rally at Xfinity Arena of Everett, Aug. 30, 2016, in Everett, Wash. Evan Vucci—AP
Republican presidential candidate Donald Trump comforts Shalga Hightower, center, as she hugs family spokesman Charmil Davis, Sept. 2, 2016, in Philadelphia. Hightower's daughter, Iofemi Hightower, was murdered in a 2007 attack at a Newark schoolyard.
Republican presidential candidate Donald Trump comforts Shalga Hightower, center, as she hugs family spokesman Charmil Davis, Sept. 2, 2016, in Philadelphia. Hightower's daughter, Iofemi Hightower, was murdered in a 2007 attack at a Newark schoolyard. Evan Vucci—AP
Republican presidential candidate Donald Trump arrives to introduce his wife Melania during the Republican National Convention, Monday, July 18, 2016, in Cleveland.
Republican presidential candidate Donald Trump arrives to introduce his wife Melania during the Republican National Convention, Monday, July 18, 2016, in Cleveland.Evan Vucci—AP

It would be hard to conjure a contest between two more dissimilar candidates. Clinton is most comfortable with nitty-gritty policy; Trump used his time onstage during a debate in Detroit to talk about the size of his penis. Clinton’s instinct is to turn questions into explanations of why her policies would help voters, while Trump prefers to brag in the first person.

The stylistic contrasts extend to their preparation. Clinton has solicited voluminous advice from her sprawling network of advisers and allies. She asks aides to print for her the best answers and insert them into a series of subject-specific binders, which are often spread across the kitchen counter that doubles as her desk these days, or an actual desk that one aide joked grows in size to accommodate the accumulating memos. Trump will entertain suggestions from his insular circle of advisers aboard his personal jet as he soars to campaign rallies. Clinton wants specifics and details; Trump wants one-liners that will be catnip for cable television.

The 90-minute contest, moderated by NBC News’ Lester Holt, will feature six 15-minute segments on subjects such as “America’s Direction,” “Achieving Prosperity” and “Securing America.” The vague parameters offer the candidates ample opportunity to steer the conversation toward preferred terrain, whether it’s Clinton’s emphasis on lifting women and children or Trump’s promise to build a border wall.

One challenge for Clinton is higher expectations. Some advisers are telegraphing that she will, as ever, be the overly prepared technocrat who can tick through detailed specifics on everything from tax policy to Tel Aviv airport access for American airliners. Others caution that Clinton is a by-the-book candidate who thinks everyone on the debate stage — rival and moderator alike — should heed the prearranged rules. Deviation there could put her off her game, and complaining about it later carries risks: aides don’t want the first female nominee of a major party to get branded as a whiner. It’s one thing to interrupt a Foreign Minister on policy disagreements in private and another to cut off a political rival in public even if he veers outside the parameters of established fact or social norms.

Meet Hillary Clinton’s Official Campaign Photographer

Formal Portrait
President Bill Clinton and First Lady Hillary Rodham Clinton prepare for a formal portrait in the East Room of the White House on the evening of the President's second inauguration, Jan. 20, 1997. Barbara Kinney, The White House
Palestine Liberation Organization leader Yasser Arafat, Israeli Prime Minister Yitzhak Rabin, Egyptian President Hosni Mubarak and King of Jordan Hussein bin Talal take a cue from President Bill Clinton, all adjusting their ties before the ceremony to sign an accord expanding Palestinian self-rule in the West Bank, Sept. 28, 1995.Barbara Kinney, The White House
President Clinton in a limousine with George Stephanopoulos and Wendy Smith, signing autographs during a Presidential tripBarbara Kinney, The White House
Hillary Clinton does a last-minute touchup in the Blue Room before the 1996 National Governors Association dinner as longtime butler James Jeffries stands nearby, Feb. 4, 1996. Barbara Kinney, The White House
President Clinton in the Oval Office after an event on the South Lawn.Barbara Kinney, The White House
First Ladies (from left to right) Nancy Reagan, Lady Bird Johnson, Hillary Rodham Clinton, Rosalynn Carter, Betty Ford, and Barbara Bush at the "National Garden Gala, A Tribute to America's First Ladies", May 11, 1994. Barbara Kinney, The White House
Hillary Rodham Clinton meets with Mother Teresa at the opening of the Mother Teresa Home for Infant Children in Washington, D.C., June 19, 1995. Barbara Kinney, The White House
The first time President Clinton met Buddy, the chocolate lab that became the family's pet. He took the dog on a walk around the South Lawn. "I asked the President if I could accompany them so I could take photos," says Barbara Kinney.Barbara Kinney, The White House
Chelsea at Ballet
Chelsea Clinton at a ballet recital at the Washington School of Ballet in Washington, DC. Barbara Kinney, The White House
President Clinton in his secretary's outer office next to the Oval Office.Barbara Kinney, The White House
Secretary of state Madeleine Albright briefs First Lady Hillary Clinton in a ladies room during a trip to Prague, 1997. Barbara Kinney, The White House
Sen. Clinton and Sen. Obama meeting unexpectedly in the back hall of the Washington convention center, the day after the last primary elections when it had become apparent that Obama had the most delegate votes, yet Clinton had not conceded.Barbara Kinney, The White House
Hillary Clinton's concession speech at the National Building Museum in Washington DC. The place was packed with her supporters as she gave her "18 Million Cracks in the Ceiling" speech.Barbara Kinney
Sen. Hillary Clinton works on remarks in a back room during the 2008 campaign.Barbara Kinney
President Clinton and Hillary Clinton on the campaign plane, heading back to Washington after one of her last campaign stops.Barbara Kinney
Sen. Hillary Clinton responding to press questions at a tense time during the primary elections in 2008.Barbara Kinney
A campaign stop in Puerto Rico during the 2008 presidential elections. It's tradition that candidates ride through town on a truck with music blaring.Barbara Kinney
Sen. Hillary Clinton greeting supporters after a speech on the campaign in Hidalgo, Texas.Barbara Kinney
Chelsea and Hillary at CGIU
Chelsea Clinton and her mother, Secretary of State Hillary Clinton, share a moment backstage at the Clinton Global Initiative University meeting at Arizona State University in Tempe, Ariz., March 22, 2014. Barbara Kinney
From left to right: Secretary of State Hillary Clinton, Dorothy Rodham and Chelsea Clinton pose for formal photos after the wedding. Chelsea Clinton was married to Marc Mezvinsky at Astor Court in Rhinebeck, NY on July 31, 2010. Mandatory Credit: Photo by Barbara Kinney
From left to right: Secretary of State Hillary Clinton, Dorothy Rodham and Chelsea Clinton pose for formal photos after the Chelsea's wedding at Astor Court at Rhinebeck, N.Y., July 31, 2010. Barbara Kinney
Presidents Bill Clinton and Barack Obama behind the scenes at the 2012 Democratic Convention.Barbara Kinney
At a Clinton Global Initiative meeting. Secretary of State Hillary Clinton and Chelsea take a selfie.Barbara Kinney
Hillary Clinton visits the Iowa State Capitol. April 15, 2015.Barbara Kinney—HillaryClinton.com
Hillary Clinton visits Capital City Fruit Company in Norwalk, Iowa. April 15, 2015. Barbara Kinney—HillaryClinton.com
Hillary Clinton visits Jones Street Java House in Le Claire, Iowa. April 14, 2015.Barbara Kinney—HillaryClinton.com
Hillary Clinton visits the Iowa State Capitol. April 15, 2015Barbara Kinney—HillaryClinton.com

Then there is the Republican. Clinton’s team and Trump’s boosters are equally unsure which version of the billionaire will show up: the braggart or the businessman? Clinton is preparing for both, although her top advisers worry the split-track preparations have left each option under-explored. The leading advice is to have Clinton behave the same way regardless, with just one or two prepackaged retorts at the ready for each of Trump’s possible provocations. “She has to be herself,” one adviser who is not in the room with Clinton says. “She already has the honest-and-trustworthy problem without showing up as someone she isn’t. She’s a nerd. She has to own that.”

Even Trump’s supporters are nervous about his scattershot preparations. Debates are among the most important moments of the fall campaign. Trump was able to skate through his primary debates by wielding snark and snide asides as a weapon on crowded stages. One-on-one contests are different. Eschewing the customary mock debates to prepare, Trump is more comfortable chewing over ideas with aides on his plane and at his houses. Instead of veteran Republican debate hands, his pre-debate powwows are filled with former Breitbart executives, family members and elected officials with whom the candidate is close.

Presidential debates have a baked-in power that no other moments in the campaign can match. A strong performance before a vast audience — including many voters tuning in to watch the candidates for the first time — can turn the tide of the race. In 2012, Republican nominee Mitt Romney clawed back into the contest with a forceful showing in the first debate against Obama, boosting his poll numbers and infusing his flagging campaign with fresh momentum and money.

But Americans’ minds are largely made up this year. Voters seem to be watching two totally disconnected, unrelated campaigns play out in partisan media and self-selected social-media accounts. That’s why many observers believe Monday night’s television — the Super Bowl of campaign 2016 — will be an emotional event and not an intellectual one. In a contest featuring the two least-beloved major-party nominees in modern times, each candidate will have to nurture a connection with the audience that will endure through Election Day.

Campaign Launch

First Primary Win

Greeting the Supporters

Family

 

Off the Plane

A Big Wave

Clinching Nominations

 

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Write to Alex Altman at alex_altman@timemagazine.com and Philip Elliott at philip.elliott@time.com