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Tipsheet

Harris' Digital Director Reveals the ‘Ominous’ Moment Where He Knew Something Was Wrong

AP Photo/J. Scott Applewhite

Semafor spoke with Kamala Harris’ former digital director, Rob Flaherty, and my, oh my, the tables have turned. For years, Democrats were the party that could tap into the culture, which partially explains Barack Obama’s 2008 and 2012 wins. Yet, as the party has become more educated, snobby, exclusionary, and dominated by elites, the vestiges of old empires are no longer suitable to win national elections. We’re in a new era: the GOP is a multiracial working-class party and young voters like Donald Trump. His crew also knew how to tap into the alternative media sphere that provided a solid foundation for a decisive win in the 2024 election. 

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It's now the Democrats who are out of touch and not in tune with the culture. It wasn’t for lack of trying. In retrospect, Flaherty and his team did try to break into alternative media space. Still, these platforms have an audience more attuned to Trump’s message than the stuffy platitudes of liberal elites. He admitted his team knew that those who weren’t political junkies were the group they needed to reach and underestimated Trump resonating on this medium. 

Flaherty also shanked the legacy media, adding that they’re no longer helpful in swaying elections. Everyone who digests news on these platforms is already a die-hard liberal supporter. They’re not as valuable. He also admitted the “ominous” warning he got when they tried to book the vice president for multiple interviews with sports media personalities who turned their backs on Harris. They wanted nothing to do with her. The inability of Kamala to break into that sphere also contributed to her defeat (via Semafor): 

The campaign needed to introduce Harris quickly to people who aren’t obsessed with politics. Sports is perhaps America’s last remaining monoculture, and Flaherty and the Harris team decided to book her on sports shows and podcasts. 

But one by one, the biggest personalities and shows politely turned them down. 

“Sports and culture have sort of merged together, and as sports and culture became more publicly and sort of natively associated with this Trump-conservative set of values, it got more complicated for athletes to come out in favor of us,” Flaherty, 33, told me in an interview last week. “It got more complicated for sports personalities to take us on their shows because they didn’t want to ‘do politics.’” 

[…] 

Faherty declined to say who turned Harris down, but she didn’t appear on key shows hosted by sports figures sympathetic to Democrats, like Colin Cowherd, Bill Simmons, or the Kelce brothers. (As Semafor first reported at the time, Harris did appear on All The Smoke, a popular but more niche basketball podcast, and NFL hall-of-famer Shannon Sharpe’s Club Shay Shay podcast.) 

The campaign’s failure to completely crack the sports sphere was, to Flaherty, ominous, and part of a larger trend in which some influencers who had felt comfortable engaging with the Biden White House, demurred when asked to help Harris make her case to their followers. “When it’s not cool to talk about politics,” he said, “you’re kind of afraid of the audience.” 

“Campaigns, in many ways, are last-mile marketers that exist on terrain that is set by culture, and the institutions by which Democrats have historically had the ability to influence culture are losing relevance,” he said. “You don’t get a national eight-point shift to the right without losing hold of culture.” 

[…] 

…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. 

[…] 

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. 

[…]

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. 

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Talk about a massive rebuild, but one that could be a force to be reckoned with—we must be on alert. Yet, voters seem to have been able to snuff out fake neo-populism since most of the messengers within the Democratic Party aren’t working-class, never have been, and don’t know what life is like outside of the Acela Corridor. The rage against those who can’t pay higher grocery bills is a prime example of that disconnect. That bill shouldn’t be back-breaking, guys. And to say ‘get a better job or an education’ is undoubtedly going to remain burned in the memories of many a Trump voter since these rants were posted on Instagram and social media. Flaherty also said Elon buying Twitter was also a critical moment in the 2024 election, as the platform pushes back, neutralizes, and slaps down liberal garbage. 

Yet, while this media discussion is primarily accurate, what about candidate quality? Harris blew through $1 billion, had top campaign talent, and got shellacked at the polls because she was a horrendous candidate who couldn’t deliver a coherent message on any issue. You can have all the money in the world and the media at your fingertips, but if the candidate is mentally defective, like Kamala, you’re not going anywhere.

And for Democrats, they have nobody who can win nationally right now. 

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