How Harris aims to keep drawing eyeballs as the hard campaigning begins

(CNN) — At a leadership retreat for top aides in Wilmington last week, Jen O’Malley Dillon – the campaign chair hired by Joe Biden and retained by Kamala Harris – ticked through the battleground states and warned them: the vice president still did not have any one sure path to 270 electoral votes.

Pennsylvania looks rough, though very possible, by their internal numbers before the debate. North Carolina, disappointing Democrats every election for the last 15 years, is feeling better to them this time around than Arizona, which Biden narrowly won four years ago. Nevada and Georgia both seem possible, though depending on the poll, can take a lot of squinting. Michigan and Wisconsin are looking like the best of the bunch for Harris, according to the campaign’s internal numbers.

As pumped as Harris aides are about her debate performance earlier this week, they don’t think it changed any of that.

That makes for a lot of potential paths to victory based on the current and projected internal data, O’Malley Dillon told them last week, but multiple top aides on the Harris campaign told CNN they fear that if the election were held next Tuesday instead of eight Tuesdays from now, Trump still would be in a good position to win.

After two and a half slower weeks since she closed out her convention in Chicago, a number of leading Democrats are stressing out that Harris could be in danger of losing the excitement and good vibes they need to overpower what they expect to be high and devoted turnout for Trump.

But that is not the feeling in Harris campaign headquarters, where many conversations focus on the 5-6% of voters still showing up undecided in battleground states, the set opinions those voters have of Trump and the continuing interest they tend to say they have in learning more about Harris. Top aides tend to talk these days about “eyeballs” and “moments,” and however many different plays they can come up with. They will keep having Harris at big rallies, but slip smaller events in between, building out the affinity groups and leaning into targeted appeals like playing up the endorsement from former GOP Rep. Liz Cheney. Harris’ appearance with the National Association of Black Journalists next week, for example, scheduled for Philadelphia on National Voter Registration Day, was a very orchestrated choice.

“There’s a quiet confidence and security in what we’re doing and the mission, but no one thinks we have this in the bag,” said a Harris campaign aide. “It’s going to be a grind until Election Day, and after.”

Harris advisers are spending their days cutting campaign ads from the debate and poring through data that they believe may show she got an important sliver of a bump. An internal summary of the campaign’s “dial groups” measuring immediate reactions, which was described to CNN, says that Harris’ best rated moment was when she spoke about abortion and Trump’s worst rated moment was when he cited a fake story about immigrants eating pets. But a dozen leading Democratic operatives and officials told CNN they worry what will happen if the campaign reverts, as it has done this week after the debate, to the standard rhythm of bus tours and stump speeches and teases of an unconventional interview or two.

Some Democratic officials have been wishfully scrolling through Taylor Swift’s Eras Tour schedule – which features three shows each in Miami, New Orleans and Indianapolis in the lead up to the election — and have begun reach out to try to get Swift to translate her endorsement into campaign concerts. The dream scenario in the minds of several of the people talking about this: either joint or parallel Swift appearances with Beyoncé.

Harris has “become a cultural political icon — politics is too small to hold it. You’ve got to do something that transcends it,” said one top Democratic official trying to make the shows happen. “An unconventional campaign means you have to do unconventional things.”

Harris HQ focusing on impact more than policy

At campaign headquarters, aides are already working toward more appearances like Harris’ online conversation next week with Oprah Winfrey instead of any big speeches or more policy rollouts like her economic plans, unless the campaign sees ways to leverage those into grabbing more attention.

Yet Harris advisers are running into limits of the calendar: unless they succeed in goading Trump into accepting a second debate, the only big event left before Election Day is the Tim Walz-JD Vance vice presidential debate on October 1.

David Plouffe, former President Barack Obama’s campaign manager, is leading the push among Harris advisers for breakthrough moments and innovative appearances. Harris and many around her tend to be dismissive of the value of traditional media, and believe they get more of a boost from putting her in situations like hugging voters during a brief Sunday stop at a spice store in Pittsburgh than she ever would from any interview.

Plouffe’s role is in part affected by the simmering tension between different factions —carryover Biden aides, new staff who came with Harris, a clutch of Obama alumni who parachuted in together and the core group of advisers who tend to spend the most time with the candidate on the road and at the Naval Observatory — although the infighting looks nothing like the dysfunction of Harris’ 2019 bid.

O’Malley Dillon’s leadership retreat last week, for example, was part therapy for aides coming off their rollercoaster summer. But it was also part information sharing — amid the massive divergence in political conditions, ballot propositions and candidates that Harris aides believe could upend the trend of recent elections where states move in regional blocs.

This year, what Plouffe is running up against is Democratic trauma from the last two presidential elections that they’ll miss basics or take advantages for granted. Plouffe himself famously predicted in June 2016 that Hillary Clinton would win over 350 electoral votes, and that was before she was widely seen to have won all three of her debates. And four years ago, Biden’s polling lead this far out from November was clearer than any that Harris has.

Translating the summer enthusiasm into fall work without the enthusiasm draining won’t be easy, said Dan Kildee, a retiring Democratic congressman from the critical battleground of Michigan. He said he’s heartened that 35,000 new volunteers signed up in his state since Harris became the nominee, but he said that won’t matter unless they’re managed and deployed correctly.

“The heft of the campaign is greater, but the work is phone calls, it’s door knocks. It’s the kind of boring stuff done with enough volume and enough repetition that we increase it,” Kildee said. “Then there’s the special sauce: can we get some of that magic?”

Obama is expected to be central in that effort, with aides working to add to his usual slate of late fall battleground campaign rallies – in person or with online influencers, whom he’s been pushing to use their platforms to get followers to vote.

The first taste of that will come next Tuesday, for National Voter Registration Day: Obama already recorded videos and other content in Chicago and at home in Washington that his office estimates will be hitting 30 million users across social media, aimed at younger voters.

“Our boss always wants to push the envelope, and the teams are aligned there. We’ll definitely be having some fun,” an Obama aide told CNN. The former president will kick off his work at a fundraiser he’s hosting for Harris next week in Los Angeles.

Former first lady Michelle Obama, who delivered a rallying cry speech in Chicago, is not expected to campaign, instead sticking with her officially non-partisan voter registration efforts.

‘There’s not that many fish left in the sea’

When it comes to volunteers and on-the-ground organizers, Democrats believe they will have an edge over Trump. They think that’s particularly true after his handpicked new chairs shut down many of the in-state offices the Republican National Committee had opened, outsourcing much of his outreach and turnout operations to outside groups.

But much like when many were working on Biden’s campaign — although to a lesser degree — Harris aides and other Democratic operatives say they know they’re still running up against voters who aren’t and won’t ever really tune in or pay attention to any of the traditional ways of getting in touch.

“The big thing we know about those voters is that they weren’t responding before and they’re voters that don’t respond to traditional media,” said Ben Wikler, the Democratic chairman in Wisconsin, where a range of in-person and texting voter-to-voter community outreach has been underway since the spring. “But also we need everyone who does pay attention to traditional media—so we have to do both.”

Mitch Landrieu, the former New Orleans mayor who moved from being a Biden campaign co-chair to a Harris campaign co-chair, told CNN on Thursday that he’s realistic about the difference between the first 50 days of Harris’ campaign, when she was energizing Democrats whom Biden had sent panicking, and the 53 days left, when she has to try to close the deal.

“She’s still trending in the right direction. And every day she’s won. And every day we’ve actually gone up a little bit,” Landrieu said. “At some point in time, you have to stop expecting it to keep going up because there’s not that many fish left in the sea.”

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