The final stretch of the longest presidential campaign in history opens this week. Think it’s been ugly? You’ve seen nothing yet.

Both Hillary Clinton’s and Donald Trump’s teams see September as the month that will make — or break — their candidate’s case for the White House. A confident Clinton fighting to keep expectations in check will ratchet up her get-out-the-vote operation while courting more Republicans to her camp. A defiant Trump will double down on the America-first message that he thinks got him this far in the first place. The Democrat's allies will continue to blanket the battleground airwaves with stinging attacks on Trump’s character. And three weeks into the month, early voting periods will open, state by state.


But nothing is more crucial for either contender than Sept. 26, when Clinton and Trump will meet at Hofstra University for the first presidential debate. Both campaigns have come to the conclusion that for the Republican nominee to compete in the homestretch, he needs a shock to the system and the Hempstead, New York, forum offers his best opportunity.

“The wildness and unpredictability of the last 16 months?” said Democratic Colorado Gov. John Hickenlooper. “It's only going to increase. It’s not going away. Hold onto your hat."

Clinton’s camp is already wary. After watching Trump try to refocus after a staff shakeup in the second half of August, stick to his teleprompter-loaded remarks, travel to Mexico to stand next to an elected head of state and then deliver a hard-line immigration speech lauded by conservative Republicans, operatives at the highest rungs of the Democrat’s operation admit to mounting worry about his ability to pare deficits in the battleground states in which she is leading by roughly 5 points or less.

At the center of senior Clinton aides’ pre-debate concern is the belief that Trump’s past few days demonstrate how low the bar is for his performance to be called a success. If simply standing next to the Mexican president is perceived as a win for Trump’s image, they complain, appearing across from Clinton will likely further elevate his standing. Indeed, Clinton’s inner circle is eager to tamp down any sign of confidence, no matter her current lead or the Electoral College map.

Trump’s inner circle agrees the stakes are high — internally acknowledging that Clinton is on track to win the White House unless the response to his debate performance is titanic. But the Republican and his allies are entering September with renewed confidence, buoyed by a narrowing in national polling, even if he remains behind in swing-state surveys. The RealClearPolitics national polling average, for example, has him down just 4.1 percentage points, a nearly halved margin from Clinton’s post-convention peak of 7.9 points in early August. The “Let Trump be Trump” faction of his rollicking campaign has claimed dominance in his debate-focused strategy sessions, while his operatives in Manhattan and suburban Washington puzzle through how to run a base-turnout election that gives him a realistic shot at 270 electoral votes.

But like just about everything in 2016, Trump’s and Clinton’s approaches to debate prep could not be more different.

The Democrat started her prep weeks ago, diving into policy briefing materials compiled by her internal teams while meeting with the experienced Democrats organizing her debate operations, often at her home outside New York City and occasionally on the campaign trail during her quiet August. Her team is led by debate veterans Ron Klain and Karen Dunn. Campaign chairman John Podesta, chief strategist Joel Benenson, and senior consultants Mandy Grunwald and Jim Margolis are also involved. So is lawyer Robert Barnett — another longtime coach — though his primary focus is on running mate Tim Kaine’s debate.

Clinton has stuck to consulting with this inner circle, which thinks general-election debates are policy discussions and that Trump can’t emerge unscathed in the eyes of undecided voters from a substantive test on the issues.

“I don’t think there’s any question — especially when it seems like the electorate is firming up and it seems like there are less and less undecideds at this point” — that the debate is an inflection point, said Democratic Ohio Rep. Tim Ryan, a prominent Clinton supporter. “It does feel like Trump’s hit some sort of a ceiling. If there’s any way to break that loose, he’s got to somehow magically understand foreign policy and complexities of domestic policy, and have to tell the truth, too."

Some political professionals surrounding Trump, meanwhile, have been urging him to start preparing for the first debate for six months, said former Massachusetts Sen. Scott Brown, an early Trump supporter, counting himself among the allies suggesting that approach.

Trump didn’t heed that advice, only recently convening his own debate-focused team of campaign CEO Steve Bannon, campaign manager Kellyanne Conway, former Fox News chief Roger Ailes, son-in-law Jared Kushner and other family members to plot strategy. He’s also consulting with former New York City Mayor Rudy Giuliani, New Jersey Gov. Chris Christie, retired Lt. Gen. Mike Flynn and Brown, said one person involved in the process, who also noted that radio host Laura Ingraham’s role is a frequent topic of discussion.

Those surrounding Trump don’t expect him to dig through policy binders, and they’re skeptical he'll participate in a mock debate — expecting him to focus instead on the top-line optics when debating a longtime pol.

"She says she’s preparing," Brown said. "She’s well versed in this area; she’s been running for offices for decades now. She’ll have a national built-in advantage because she’s been a politician her whole life, and you’re running against someone who hasn’t. He’s not as filtered as she is; she hasn’t driven in 20 years. She seems kind of uneasy hanging out with people; she can’t yuk it up like one of the guys or gals and talk about the Red Sox or the Jets. Trump can — he brings the everyman appeal."

Clinton’s prep team has, accordingly, puzzled through making her look trustworthy, suggesting ways for Clinton to pin down Trump on policy and expose his lack of knowledge.

“In a two-person debate; it’s not going to work to say, ‘I’ll take care of this; I know more than the generals, believe me,’” said former Pennsylvania governor and longtime Clinton friend Ed Rendell. “You actually have to be substantive."

But they remain concerned about Trump’s unpredictability, as Clinton privately acknowledges to donors. Before selecting its stand-in, her campaign was flooded with tentative offers from supporters eager to play the Trump role in mock sessions — even getting one from former Michigan Gov. Jennifer Granholm. (She was kidding, she said: “I’m probably too short.”)

Still more complications are piling up: Clinton friends say she is leaving open the possibility that Trump agrees to only one debate, increasing the urgency of appealing to as many constituencies as possible in 90 minutes. They also expect him to threaten to pull out of the debate in the weeks leading up to it as a way to heighten the drama, and to agitate for the inclusion of Libertarian candidate Gary Johnson — a fate the Clinton camp is desperate to avoid.

Her team is also grappling with the difficulty of preparing the candidate to debate an opponent so inconsistent that he could either throw personal insults, mocking her in the way he did his GOP primary opponents, or offer a more presidential presence, as he attempted last week in Mexico.

“It’s a difficult thing to debate a chameleon,” Hickenlooper said.

Trump forces are eager to cultivate the unpredictability mystique. They’re also eager to lower expectations.

“The debates may turn out not to be the spectacle people think they are: Both candidates are seasoned debaters at this point,” said former Georgia Rep. Jack Kingston, a Trump adviser. “I just don’t see Hillary Clinton slipping in a debate."

Nonetheless, new confidence has burst into Trump’s everyday interactions since he installed Bannon and Conway, say associates. Bannon has convinced Trump to stick to scripted speeches written by him and policy aide Stephen Miller, which people in Bannon’s orbits see as a critical development.

That’s not to say there aren’t still competing centers of influence within the Trump infrastructure, as Kushner plays an outsize role and Giuliani finds himself ever more firmly ensconced. But those guiding Trump have concluded that turning the remaining months into a base election — the kind of appeal with which the candidate is most comfortable — is his only realistic path to victory.

Clinton’s team and her supportive super PAC, Priorities USA Action, have booked tens of millions of dollars worth of television airtime for Trump-savaging ads over the coming stretch, but Trump’s campaign has promised to go on air only in the coming week, pulling together a small buy that isn’t supplemented by much super-PAC firepower as major Republican donors remain on the sidelines.

Clinton’s cash-rich camp, meanwhile, has been eager to expand the map, adding an initial Arizona purchase to its portfolio last week, while leaders of the super PAC have been meeting and holding conference calls to consider expanding into Arizona and Georgia — two states where the group has been actively polling for weeks.

This week Clinton’s campaign is shifting into a get-out-the-vote mode while she also maintains her sideline pursuit of poachable Republicans. Her team will continue touting prominent GOP endorsements: Former California gubernatorial candidate Meg Whitman even introduced Clinton at multiple closed-door August fundraisers in California. There, the candidate explained her approach to Republicans interested in Trump, according to one Bay Area attendee. Clinton divides Trump voters into two baskets, she said: the everyday Republicans — her targets — and what she called “the deplorables” — the "alt-right" crowd she excoriates and has no hope of wooing.

Clinton will substantially ramp up her campaign travel schedule in September, focusing on national security issues this week. Her team will also step up its surrogate activity, planning at least one major appearance from Clinton, Kaine, former President Bill Clinton — who will reappear on the trail after some time focused on fundraising — President Barack Obama, Vice President Joe Biden and Sen. Bernie Sanders every day.

That starts Monday, with Sanders in New Hampshire, Biden in Pennsylvania, and Bill Clinton in Michigan and Ohio.

But all that is simply a way to count down to the moment that might seal their presidential fate.

“Debates,” said Ryan, "are really the only opportunity to try and shift a campaign."

Eli Stokols contributed to this report.

