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Here's Hillary Clinton's Back-to-School To-Do List

Labor Day may no longer be the kickoff of presidential campaigns, but it marks their homestretch. Here is Hillary Clinton’s to-do list.
Image: Hillary Clinton
Democratic presidential candidate Hillary Clinton gestures as she speaks at a campaign event at Truckee Meadows Community College, in Reno, Nev., Thursday, Aug. 25.Carolyn Kaster / AP

Labor Day may no longer be the kickoff of to presidential campaigns, but it now marks their homestretch: Americans come back from vacations, spend more time watching TV (including political ads, news and debates), and begin to focus on the election.

Heading into the holiday, Hillary Clinton enjoys some obvious advantages over Donald Trump that most presidential candidates would kill for: She’s ahead in the polls, has raised more money, has run more ads, built the bigger ground game, enlisted more bold-named allies, peeled off more defections from the opposing party and inherited a better electoral college outlook.

It’s easy to see why Democrats are feeling confident, with David Plouffe predicting to Politico Friday that Clinton is already sitting on 347 electoral votes — a landslide over the 270 needed to win.

“I think the campaign is fundamentally over,” said veteran Democratic strategist Bob Shrum. “It formed in August, post-convention. Trump always had a very steep mountain to climb. And instead of climbing the mountain, he keeps falling off it.”

Related: FBI Releases Notes From Interview With Hillary Clinton

But as the past two weeks have demonstrated, Clinton also faces some major persistent challenges, which help explain why many Democrats closer to Clinton remain nervous.

The first two weeks of August were some of the best of Clinton’s campaign. With the Olympics and Trump’s self-sabotage attracting all the attention, Clinton plugged away blissfully out of the gaze of cable news, getting her message out in the local press and in paid advertising, which she had almost entirely to herself.

The second two weeks of August, however, were a return to the oobleck of scandal and media haranguing that Clinton has slogged through so often in her public life. She used the time to stockpile a whopping $143 million in August, which will keep her from having to leave the campaign trail in September or October.

But all that time behind closed doors helped a newly improved Trump campaign advance their own message about Clinton's ethics and inflamed relations with the press. Her polling lead slipped as the race tightened.

Related: DNC Expands Footprint in Arizona, Georgia, Utah

The final two months of the campaign are far more likely to look like the second half of August than the first.

As people in their orbit like to say, nothing comes easy for the Clintons, and there’s a history of snatching defeat from the jaws of victory. To prevent that, here is Clinton’s Fall to-do list:

Find a detente with the press: It’s been more than 270 days since Clinton held a formal press conference and complaints about access have poisoned relations with her press corps to the point that it sometimes eclipses the news she wants to get out.

Trump has held 17 press conferences this year, and while few voters, if any, will cast their ballot based on press conferences, the perception that Clinton is hiding from tough questions plays into a potent existing narrative that she is not being forthright — something Trump is eager to exploit with his “Hiding Hillary” meme.

August was the worst month of Clinton’s 2016 campaign in terms of press access, with just two national news interviews (both via telephone), one sit-down with Jimmy Kimmel (who not a journalist), one short Q&A with journalists at a conference (which went poorly), and only two open campaign events (at which she did not take questions).

And unlike President Obama or other former candidates, Clinton has not allowed press into her fundraisers, which consumed much of the month.

But at least some change is coming. Clinton will look to at least defuse the tension on Monday when she travels on the same plane as her press corps for the first time this year — something Trump does not do — and potentially take questions. After decades of strained relations with the media, Clinton may not be pals with the reporters who cover her, but she can at least lower the heat.

Stabilize her image: No matter what Clinton does, Americans don’t seem to like her. She remains the least popular Democratic nominee in polling history, and a Washington Post/ABC News poll clocked her this week with the worst approval rating of her entire 25 years in national public life.

Democrats close to Clinton’s campaign say the issue is not a major barrier to victory since the damage is already baked into the cake, after more than a year of persistent questions on her email server and the Clinton Foundation.

But if Clinton wins, she’ll have a hard time governing effectively unless she can begin to improve the way people see her.

Make sure the election is a referendum on Trump: Since Clinton can’t win the election on her popularity, her saving grace is Trump — the only major party nominee in history whose numbers are worse than hers.

The latest Fox News poll shows Clinton ahead of Trump on issues that had been seen as his strong suit — the economy and fighting terrorism — while he has slid below her on trust and honest, two of her biggest weaknesses.

Clinton’s core message has been that Trump is not fit to be president, which implicitly plays to her strengths of experience, competence and steadiness. “When she's been at her best is when she does that compare and contrast. Campaigns are choices,” said Democratic strategist Chris Lehane.

With plenty of material to attack Trump with, Clinton will look for new opportunities to call attention to the contrasts between the two candidates.

Weather the storm: The final two months of the campaign will be ugly. Following the hiring of Breitbart chairman Steve Bannon as CEO, Trump again signaled his commitment to trash Clinton with his hiring this week of David Bossie, the President of Citizens United, whose anti-Clinton documentary prompted the namesake Supreme Court campaign finance ruling.

There’s the FBI notes from their investigation in Clinton’s email server, released Friday, the upcoming release of her State Department schedules, new emails from Judicial Watch, whatever Julian Assange is sitting on at Wikileaks and who knows what else.

Clinton may decide it’s better to take her licks by not responding to every question rather than to elevate the drip-drip-drip into something more serious, but it will be an uncomfortable ride either way.

Win the first debate: When Democrats think about what could possibly go wrong for them, the first thing most consider is a bad debate. Clinton is an expert debater while Trump is a novice whose record in the Republican primary was mixed at best.

But Trump is unpredictable and his rock-bottom expectations will be easy to surpass. Former Obama aides still remember the president’s poor performance in the first 2012 debate as one of the lowest moments of the campaign. “[Trump's] last remaining shred of hope is the debates,” said Shrum.

That’s why Clinton is leaving as little to chance as possible by spending hours preparing for the debate as aides try to come up with every possible attack Trump could throw at her.

Assemble the team: Democrats have yet to deploy the full firepower of their surrogate arsenal, but it’s coming, say Clinton aides. Bernie Sanders will hit the trail for Clinton in New Hampshire on Monday, Bill Clinton is coming back from Siberia on Tuesday to campaign in North Carolina, and President Barack Obama and his Vice President Joe Biden will be out again soon. As down ballot races pick up steam, almost every Democratic candidate in America will amplify Clinton’s message by using Trump as a cudgel against their Republican opponents.

Meanwhile, Trump is facing off against the Democratic hordes almost entirely by himself, with major Republicans either abandoning him or fleeing the cameras to avoid being asked about him.

Maintain air of superiority: Political operatives talk about two “tracks” for getting your message out: “Earned media” (the press) and “paid media” (advertising). Clinton aides realized months ago that they could never compete for Trump in the earned media space, give his preternatural ability to make the world pay attention to him.

But Clinton is outspending Trump 10-to-1 on the paid airwaves while also continuing to increase her cash in the bank, thanks to prodigious fundraising.

Not only has Trump been slow to raise money and then spend it on ads, but the deep-pocketed super PACs that typically boost Republicans have stayed on the sidelines. The cavalry is not coming for Trump and every day that goes by is another without the fundamentals of the race changing in his favor.

Get out the vote: Early voting in some states starts in just three weeks, and eventually 35 states and the District of Columbia will allow people to cast ballots before Election Day. Clinton’s campaign has spent the past 18-months building a state-of-the-art field and data program, updated from Obama’s 2012 operation, that will grow to thousands of paid staffers. Trump is lagging well behind with just 88 offices to Clinton’s 291, according to a PBS NewsHour tally.

Political scientists say good get-out-the-vote operations are worth about 1-3 percentage points, which is more than enough to win a close presidential election. And with so many paths to victory and superior resources, Clinton will continue working to spread Trump thin by making him defend places like Arizona and Georgia.

Shore up white swing states: While Clinton is over-performing in diverse red states like Arizona and Georgia, she’s underperforming in predominantly white swing states like Nevada and Iowa, which have large populations without a college degree.

Clinton may not need these states to win, but both went for Obama in 2008 and 2012 and have down-ballot races Democrats want to win, so she’d like to find a way to win, too.