Kamala Harris’ digital chief on Democrats ‘losing hold of culture’

In July of 2023, a year before Harris became the nominee and as the Republican primary campaign was underway, I spoke with Flaherty, who was then running digital strategy for the White House.

There, he had helped shape the White House’s alternative media strategy, working to help support its own network of die-hard supporters, and dishing out exclusives to alternative liberal media; some of Biden’s first interviews after he nominated then-Judge Ketanji Brown Jackson to the Supreme Court last month went to the popular Substack writer and professor Heather Cox Richardson and the left-leaning news YouTuber Brian Tyler Cohen.

Flaherty was also paying close attention to how the race was being run on the Republican side. Donald Trump was leaning into new podcasts, and his opponents were tapping a large network of right-leaning and conservative personalities to amplify their message.

Then, he acknowledged that the Republican Party had done a better job building up its alternative digital media ecosystem with podcasters, YouTube streamers, and friendly pundits. But he argued that the then-Biden campaign would overcome those obstacles by better navigating the “personalized internet,” by which sophisticated algorithms feed Americans highly specific information tailored to their tastes and online behavior.

Speaking with me again last week, Flaherty said that remained their theory of the case the entire time. The campaign knew from the beginning that the race was going to come down to voters who do not pay attention to politics or mainstream news and instead get their information from people on YouTube, their friends’ Instagram stories, or links or memes dropped in a group chat.

This firstly meant a shift in paid advertising from previous campaigns. Instead of just blanketing the airwaves in the battleground states, the campaign also invested heavily in ads on YouTube, recognizing the rapid growth in streaming. That’s where, the campaign’s data showed, many of Harris’ key voters were spending their time.

More importantly, this meant building out a strategy focused more on podcast appearances and interviews with influencers than on traditional media. Flaherty said the campaign skipped opportunities to talk to the major legacy news outlets because of Harris’ extremely limited time and its survey data, which showed that their audiences overwhelmingly supported Harris already.

“There’s just no value — with respect to my colleagues in the mainstream press — in a general election, to speaking to the New York Times or speaking to the Washington Post, because those [readers] are already with us,” Flaherty said.

Flaherty isn’t dismissive of television and other legacy media. “One of the most important moments of the campaign for the vice president was her interview with Bret Baier. That was a huge fundraising moment. It was a huge social moment,” he said.

“When Trump did the McDonald’s thing, it was smart, because it was a thing that obviously drove television coverage, but it also drove social media engagement too,” he said. “And those things often happen in tandem, but they don’t always, and so it was the sweet spot. It drove traditional coverage and nontraditional media. I don’t think TV is dead. It’s still probably the most important thing, but it’s the literal TV and what’s on it that matters.”

As the campaign wore on, though, Flaherty said he realized their failure to gain traction in certain corners of media reflected a deeper problem — one that wasn’t solved when Harris replaced Biden on the ticket. The Harris campaign, representing what many voters saw as an embodiment of the status quo, was running contrary not just to ideological distrust of establishment figures but to media trends. The media successes of 2024 were independent, nontraditional online personalities who themselves were avatars of the rewards of going up against the Establishment.

“The reason folks are seeking alternative sources of media and are turning away from political news is because they don’t trust our institutions. They don’t trust elites, they don’t trust the media, they don’t trust all this stuff. So the party of elites and institutions is going to have a hard time selling to people in these places,” Flaherty said.

“It’s not as simple as, like, ‘Go to Joe Rogan and talk about how great democracy is and the importance of preserving the independence of the DOJ,’ or whatever. You’ve got to speak their language. And I think there are plenty of cultural touchpoints. I mean, Joe Rogan was at least recently, for Medicare for All. Theo Von is really against money in politics and the way that pharma has flooded our communities with opioids. Those are all things that Democrats have something to say on. But as long as we seem like the party of the system, the people who are anti-system and are looking for anti-systemic media — we’re gonna have a hard time connecting with them.”

Nowhere was this more clear than within the “manosphere” of podcasters and content creators like Rogan and Von. To them, Trump had become less toxic and more based, and he rewarded his supporters with access. Flaherty said the Trump campaign successfully used new media to reshape culture, while Democrats found that the mass media institutions that had long largely supported them were weaker than these new cultural drivers.

“It’s more than just young men. It’s a broader ecosystem,” he said. “Democrats have historically had these really close relationships with institutional media, institutional culture — Hollywood and the traditional press. There’s this entire cultural ecosystem that the Trump campaign did a really good job of cultivating over a long period of time.”

Flaherty also acknowledged that Elon Musk’s purchase of X, née Twitter, played a major role in the campaign, further tilting the scales of online culture and information towards Trump.

“Its importance was twofold. One, it was where you reach elites and high-information people. But two, it was also the kind of place where politics could sort of careen into culture. And so it was a really important central node, even if it wasn’t the farthest-reaching platform,” he said. “Having that node be fundamentally controlled by, effectively, an arm of the Trump campaign was not good. Really a problem. And so Elon obviously sort of achieved his ends there. It was obvious that center-left and left content was being throttled compared to right content.”

But while the campaign came to believe it was fighting an uphill battle against culture moving in the opposite direction, it also made some strategic errors of its own, based on faulty assumptions.

Flaherty said that one place he underestimated the Trump campaign was the central part of the former president’s digital strategy. The Harris campaign thought that the Trump team’s decision to continue talking to the manosphere meant he would simply be reaching the same audience over and over. But the “incredible frequency” of those appearances helped build the former president’s credibility with that audience, which seeped out, Flaherty said.

He also said the Harris campaign never quite figured out one of its earlier strategies, which was to get its messaging organically into family group chats and private media, partially because they couldn’t nail what kind of content would spread that way.

“I think that’s one that ended up being a lot harder to execute on,” he said.

Over the last several weeks, many professional Democrats I’ve spoken with feel that they have successfully identified their problem. But the next steps for Democrats’ media strategy are uncertain. When I met Flaherty this week in New York, he was contemplating his own professional future, and what his role would be — if any — in shaping the next four years of media strategy for his party and finding a way to regain the upper hand online.

To Flaherty, part of this starts with putting real effort into building the left and center-left’s own independent media ecosystem, divorced from the nonpartisan media that has historically satiated Democrats’ appetite. Flaherty said the one silver lining of the election was that many hardcore Democratic partisans have begun to waver from their satisfaction with legacy media.

“They’re never going to not trust The New York Times, and they’re never going to distrust the Washington Post,” he said. “But I think that in a Trump era, you’ll start to see frustrations with the mainstream media come to a boil. And I think there will be smart people who try to fill the gap — more individuals who create content on left and center-left messaging.”

Flaherty said that Democrats need to invest in boosting independent partisan friends online — as well as content creators and media figures who haven’t been explicitly political but could reflect liberal and progressive values — to counter the surging online pro-Trump right.

“We need a whole thriving ecosystem. It’s not just Pod Save America, though I think we should have more of them. It’s not just Hasan Piker. We should have more Hasan Pikers. It’s also the cultural creators, the folks who are one rung out who influence the nonpartisan audience. Those things all need to happen together,” he said. “And the reality is, it’s not going to be big media organizations. It’s going to be a network and a constellation of individual personalities, because that’s how people get their information now.”

Flaherty said he believes the ecosystem needs to grow “in order to sort of simulate demand. As people run away from cable, the center-left starts to distrust mainstream media, and as the mainstream media outlets become more reliant on their mostly center left subscribers — all of this is going to kind of happen in tandem.”

In the weeks since Trump’s reelection, savvy and clueless media observers alike have chalked up Harris’ problems in the media to small decisions, like her failure to appear on Rogan’s podcast (a moment that Flaherty acknowledged was a missed opportunity).

This misunderstands a simple aspect of the media strategy that we gleaned from speaking with both the Trump campaign and the Harris campaign about their approaches to new media.

Ultimately, their media strategies weren’t particularly different. Both campaigns leaned hard into alternative new media — Trump because he could reach large audiences and avoid annoying questions about various political scandals, Harris because her campaign felt the younger and nonwhite voters Democrats had long relied on were less tuned into legacy media.

The outcomes were different because — from sports podcasters to longform talk comedy bros — the current class of online influencers and their audiences preferred both Trump’s style and his anti-establishment message.