Both teams prepare for the biggest moment of 2016 – the Sept. 26 debate.

By Gabriel Debenedetti
09/04/16 – 07:11 AM EDT

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.

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