Donald Trump and Kamala Harris sprint toward September debate

WASHINGTON — With the summer political conventions complete, the traditional nine-week sprint from Labor Day to Election Day begins, as the Harris-Walz and Trump-Vance campaigns look to shore up their bases and win over the undecided voters political analysts say pay closer attention to the race in the fall.

After a fast-moving summer that saw former Republican President Donald Trump survive an assassination attempt and Democratic Vice President Kamala Harris ascend to the top of the ticket after President Joe Biden withdrew from the race, both candidates are ramping up their campaign appearances and fundraising appeals.

"Hold on to your hats, it's going to be wild and woolly," said Republican campaign strategist Michael Dawidziak, of Bayport, who worked for the campaign of the late President George H.W. Bush.

Polls show Harris giving Democrats a bump since entering the race, but she and Trump remain in a statistical dead heat in most battleground states, where polls show the race is within the margin of error.

Harris leads Trump by an average of 1.7 percentage points in national polls conducted between Aug. 5 and 26, according to poll tracking website Real Clear Politics. But the polling gap is much narrower in battleground states, where Trump averages a 0.01 edge over Harris.

As Trump and Harris work to close the polling gap, here are five things both campaigns are gearing up for.

Debate prep

Both candidates have agreed to square off for the first time in a Sept. 10 debate hosted by ABC News in Philadelphia.

The debate’s earlier-than-usual timing — with past presidential debates typically occurring in late September and October — gives both campaigns the chance to reach more undecided voters who historically already have made their choice by October, said Conor Dowling, a political science professor at the University at Buffalo.

"There's certainly going to be a few more undecided voters in early September compared to late September," Dowling said. "I think for Harris it's about solidifying support and maybe trying to gain a little more, and then for Trump, it's also about trying to maybe gain a little more support among undecided voters, maybe by trying to appeal to those folks who maybe were supportive of [Robert F. Kennedy] Jr."

Kennedy ran as an independent, but suspended his campaign Aug. 23 and immediately endorsed Trump, who later named Kennedy as an honorary co-chairman of his presidential transition team.

The debate rules were finalized after both campaigns argued over whether microphones can be kept on throughout the debate. Ultimately, debate organizers said it will not allow mics to be kept on when it's not a candidate's turn to speak. Other rules include no written notes from the candidates and no live audience. While the Trump campaign has accepted the rules, the Harris team maintains it has not signed off on them, according to Harris' senior adviser Brian Fallon.

Republican JD Vance and Democrat Tim Walz are scheduled to face off Oct. 1 at a vice-presidential debate hosted by CBS News in New York City.

Battleground blitz

As Harris looks to build upon the 2020 map to victory that ushered her and Biden into the White House, including flipping Georgia, Trump will look in part to replicate his 2016 map where surprise wins in Wisconsin and Michigan gave him the edge in the Electoral College, despite losing the popular vote to Democrat Hillary Clinton.

"At this point in a campaign, with the respective party faithful all revved up from the conventions, they both should be pivoting toward moderate voters who decide any close election, and the place where you’ll find more of these unaligned swing voters is the suburbs," said Lawrence Levy, executive dean of Hofstra University’s National Center for Suburban Studies and an expert in suburban politics.

Expect both campaigns to spend a lot of time in the swing state of Pennsylvania, which Trump won in 2016, but Biden flipped four years later. Trump, who was leading Biden by an average of four percentage points in state polls during the summer, has seen that margin virtually vanish to an average of less than one percentage point — 0.02 — since Harris’ entry, according to Real Clear Politics.

Across the battleground states of Arizona, Georgia, Michigan, Nevada, North Carolina, Pennsylvania and Wisconsin, Trump only holds a 0.01 point polling lead over Harris, according to the latest analysis posted by Real Clear Politics on Aug. 27.

"It's kind of down to a few states, and they've got to figure out which messages and which targeted issues work in those states," said Democratic campaign strategist Hank Sheinkopf of the challenge ahead for both campaigns.

An 'October Surprise'?

Political campaigns tend to brace themselves for an "October Surprise" — a term coined in the 1980s for scathing news that could change the course of the election.

In 2016, just as Trump was grappling with a dip in support and calls to suspend his campaign following the early October emergence of an "Access Hollywood" tape where he could be heard boasting off camera about grabbing women without their consent, his opponent Clinton would come to deal with her own October surprise, when then-FBI Director James Comey announced two weeks before Election Day that he was reopening an investigation into her use of a private server for State Department emails.

Dawidziak said because of all the twists and turns the presidential race has taken this summer, voters already may be conditioned to expect the unexpected.

"Because Harris has been vice president for four years and Trump's been president, and this is his third time he's running, there's not a lot unknown about these candidates, so if there's going to be an October surprise, it's probably going to be self-generated," said Dawidziak, referring to potential gaffes and missteps on the campaign trail. 

Transition preparations

Both campaigns have started building their presidential transition teams, a move usually taken in the final months of an election, to allow the eventual victor to have key appointees and staff in place.

The Trump campaign has named Kennedy and former Democratic Rep. Tulsi Gabbard as honorary co-chairs of his transition team. The group is currently led by Linda McMahon, who served as Trump’s Small Business Administration administrator, and billionaire financier Howard Lutnick.

Harris has asked Yohannes Abraham, who served as executive director of the Biden-Harris 2020 transition, to aid with the transition effort, according to The Associated Press. Abraham currently serves as the Biden administration’s ambassador to the Association of Southeast Asian Nations.

The federal government typically provides office space and resources to both campaigns to aid their transition staff, but the campaigns must first accept the aid. In 2016, Trump came under scrutiny for bucking the tradition of using federal office space for his transition and instead relying on his Trump-branded properties, including Trump Tower. In 2020, Trump stonewalled Biden's transition efforts, directing White House officials to delay the release of information to Biden's transition team as Trump refused to accept the election results.

Max Stier, the president and CEO of the nonpartisan, nonprofit Partnership for Public Service, which historically has aided candidates with the transition effort, said a smooth transition process is critical to the public trust.

"Only about half of the country expects a peaceful transfer of power after this upcoming election, and this increased doubt is driven in part by a lack of trust in the presidential transition process itself," Stier said in a statement. "One way to help to rebuild this weakened trust is for both Harris and Trump to demonstrate that they are taking the necessary steps to plan for a smooth and effective transfer of power. Accepting the [General Services Administration’s] support will send a much-needed signal to the public that they are doing just that."

Raising money, money, money

This presidential campaign cycle is on pace to be the most expensive to date — with both campaigns projected to spend a combined $2.16 billion on media ads, up 17% from the 2020 campaign, according to a recent report by AdImpact, a political advertising analysis firm.

Both campaigns will look to squeeze in as many high-priced fundraisers as they can between major campaign events, Dawidziak said.

"Every campaign has very valuable advance teams whose job is to schedule campaign fundraisers. They’re the ones who will say, ‘We can get to this fundraiser and still get to this rally by six o’clock.’ I would assume both campaigns have top-notch advance teams," Dawidziak said.

Long Island has been part of both campaign's fundraising strategy — Trump held a fundraiser in Bridgehampton on Aug. 2, and second gentleman Doug Emhoff hosted a trio of East End fundraisers this summer in Water Mill, Fire Island Pines and Sag Harbor.

By Laura Figueroa Hernandez

laura.figueroa@newsday.com@Laura_Figueroa

Laura Figueroa Hernandez is the White House correspondent and previously covered New York City politics and government. She joined Newsday in 2012 after covering state and local politics for The Miami Herald.