How Philanthropy Lost Touch with Working-Class Americans—in Three Acts
Since Inauguration Day, I’ve been watching closely to see what those inside the bubble of institutional philanthropy are actually saying out loud. This week, David Callahan said some things that struck me as more than the usual analysis. It read like a quiet indictment. He noted that many progressive foundations, early on, locked into the idea that Trumpism was simply a “whitelash” — a wave of racial resentment from white voters — and built their grant-making strategies around that belief. They assumed Trump’s racism and nativism would automatically drive multiracial solidarity on the left. That assumption became strategy. And strategy became how and what they funded.
But, if these institutions so badly misread the rise of Trump, it raises a harder question: have they been out of touch, not just with conservatives, but with the broader public itself? What if the disconnect wasn’t ideological, but civic? What if Big Philanthropy stopped listening to working-class Americans a long time ago?
Perhaps Callahan isn’t ready to go all the way there, but he gestures in that direction clearly enough. “Things are turning out very differently,” he admits. In truth, they turned out the opposite of what many progressive funders expected. Trump and other Republicans have made gains with voters of color—especially Latino men—across two election cycles. The right, not the left, is now closer to assembling a multiracial working-class coalition.
Tellingly, Callahan acknowledges that Trump’s support base goes far beyond the caricature many on the left clung to: “While Trump’s base does include the most racist, sexist and xenophobic voters in America,” he writes, what progressives missed—thanks to a lack of curiosity, confirmation bias, and groupthink—was the broader appeal of Trump’s message: disruption, resentment of elites, and the promise of an outsider willing to break the system. But the foundations in Callahan’s orbit didn’t want to hear that. They funded the story they believed in, not the one unfolding on the ground.
And, now, in a moment of political backlash and financial scrutiny, those same institutions are asking everyday Americans to stand with them against proposals for increased oversight and higher excise taxes on their endowments. It’s a tough ask. Because the truth is most people haven’t seen that tax-incentivized wealth show up in meaningful ways—not in their neighborhoods, not in their schools, not in their civic life. When Big Philanthropy backed the wrong theory of change and cut itself off from the concerns of working-class Americans, it made a trade-off. And now the cost of that trade is coming due. Loyalty depends on relatability—without it, the politics don’t matter.
What’s difficult for some to grasp is that this isn’t the beginning of the story. We’re already in the third act—and maybe, for philanthropy as we know it, the final one. Not because foundations will disappear, but because the public’s patience with institutional self-congratulation is running out. The gap between how Big Philanthropy sees itself and how working-class Americans experience it has grown too wide to ignore. If they want to survive with any moral authority intact, it needs to understand how we got here. That means rewinding the tape to at least the second act when the drift began.
The Second Act: The Drift
To his credit, Callahan isn’t just naming uncomfortable truths; he’s doing his homework. In tracing how funders lost the plot, he points to people like Patrick Ruffini, whose book Party of the People: Inside the Multiracial Populist Coalition Remaking the GOP has been praised as “the book that predicted the 2024 election.” Ruffini doesn’t reduce the Trump coalition to a caricature. Instead, he looks closely at how culturally conservative, working-class voters—across race and region—have drifted from the Democratic Party and found something familiar, if not always comfortable, in the GOP. Callahan draws on Ruffini’s analysis to explain how this realignment happened and why elite institutions, including philanthropy, didn’t see it coming.
The story Ruffini tells—focused on the past decade of voter trends—doesn’t revolve around policy or platforms. It’s about identity, instinct, and disconnection. In places like Starr County in South Texas, once deep-blue Democratic strongholds, Trump made historic gains not by offering a detailed plan but by tapping into a cultural mood. Working-class voters who felt alienated from elite liberal norms on religion, gender, speech, and the role of government didn’t flip all at once. They drifted. And that drift became a pattern. In Ruffini’s terms, it wasn’t persuasion. It was a preference cascade. Once voters saw people like them switching sides, they began to wonder if they should too.
Callahan doesn’t sugarcoat it. He points out that progressive institutions assumed Trump’s racism would harden loyalty among voters of color—that his extremism would spark intersectional solidarity. But that assumption overlooked something basic: many of these voters were never ideologically progressive to begin with. Their loyalty was shaped by other forces like community, tradition, habit, and local infrastructure. Many voters weren’t responding to Trump’s ideas, but to the absence of a deeper sense of place and connection. It wasn’t ideology that anchored them; it was relationship. And once those supports weakened, their votes became more fluid. In the absence of civic rootedness, partisan loyalty became just another preference—one that could shift, drift, or disappear altogether.
Yet this is only the second act. There’s still more homework left to do. This was the quiet unraveling of assumptions—the movement of people who no longer felt held by the institutions that once shaped their choices. It was the moment when identity stopped predicting behavior and gut instinct took the wheel. Ruffini gives us the map. Callahan has the courage to point to it. And, together, they help us see how elite institutions—political and philanthropic alike—missed the ground shifting beneath them. But this realignment didn’t begin in 2016 or 2020. To understand why the drift happened at all, we have to start at the beginning with the first act, when the civic scaffolding that once held people in place began to disappear.
The First Act: The Collapse
Erika and I raised our family in Pennsylvania. And, like a lot of folks who live here, we’ve watched as our state has become a regular focus of national attention, especially during election season. Western Pennsylvania, in particular, is sometimes treated as a political weathervane—a place people point to when they want to explain what’s happening with working-class voters in America. In Rust Belt Union Blues: Why Working-Class Voters Are Turning Away from the Democratic Party, Lainey Newman and Theda Skocpol take that focus seriously and give it real depth. They don’t just examine how people voted. They look at what held those votes in place for so long and what caused that structure to come undone.
In small communities around Pittsburgh, union halls once served as the backbone of civic and political life. They weren’t just places for contract negotiations; they hosted fish fries, weddings, retirement parties, and ward meetings. Politics didn’t feel distant or abstract. It was part of the rhythm of life. Voting Democrat wasn’t about a specific issue platform. It was about who you were. Party loyalty, as Newman and Skocpol write, was “in large part about socially embedded identities and mutualities.” And, for a long time, that identity was clear. In the mid-twentieth century, one retiree told the authors, “there wasn’t a Republican in the world who took care of the working guy.”
But, over time, that ecosystem began to disappear. Some of it was economic: industry declined, jobs vanished, unions weakened. Some of it was cultural: national politics grew louder while local institutions grew quieter. And some of it was neglect: the party stopped investing in the very places where its relationships had once been strongest. As those civic bonds broke down, the loyalty that came with them began to fade. Workers didn’t switch sides overnight; they just no longer felt tethered. And, once that connection frayed, something else inevitably filled the space. As the union halls went dark, other institutions filled the gap. More than 250 NRA-affiliated gun clubs operate within 100 miles of Pittsburgh. Thirty-four megachurches are active across the state—six in that same radius. When one form of belonging fades, another is always ready to take its place.
This is the first act: the part of the story that moves slow enough to ignore until it’s too late. And it’s the hardest kind of story to make sense of because it doesn’t show up in polling data. It requires listening over time, noticing what’s gone quiet, and asking questions we’ve been trained not to ask. As much as the pundits want us to think otherwise, this didn’t start with Trump. It started with loss—with a slow unraveling of the institutions that once made people feel like they belonged somewhere. Everything that followed began right here. And if this sounds like a warning meant only for Big Philanthropy, it’s not. Nonprofit leaders across the country, especially those whose organizations once shared a local presence with labor halls, should take this reckoning just as seriously.
Out of Touch and Asking for Help
I admire that Callahan is pushing his colleagues to make sense of themselves. But I’m not sure he’s naming the deeper truth—the one that undercuts what I suspect is his greatest concern. Progressive philanthropy’s response to Trumpism has never really been about changing the electorate. It’s been about signaling virtue within its own circles. The real audience was never the disillusioned voter in western Pennsylvania or the Latino working-class dad in South Texas. It was theater for the boardroom, the funder collaborative, the social feed. The programs were designed to impress peers, not to engage the working-class Americans who would eventually show up at the polls.
And that’s the problem. No matter which act you start with, the conclusion is hard to escape: just as many are saying about the DNC, institutional philanthropy is out of touch with working-class Americans. It’s out of touch with their values, their realities, their civic lives, and their needs. That’s true in red towns and blue ones. It’s true among voters who drifted right and among voters who simply stopped showing up. And it’s not a recent misstep. It’s a long pattern nearly three-quarters of a century in the making. The institutions that once connected people to public life have been slowly eroded, underfunded, or ignored. And philanthropy, by and large, has watched it happen from a distance.
Instead of righting that wrong, these elite institutions doubled down on top-down strategies built on abstraction and self-assurance. They assumed that moral clarity, demographic inevitability, and national messaging would carry the day. And, now, in a moment of real vulnerability, they are turning to the very people they overlooked and asking them to defend tax privileges, protect endowments, and rally around institutions that never really showed up for them in the first place.
Whether there’s much time left to change course, I’m not sure. But I’m confident of this: double-checking the locks on the vaults or spinning a better story won’t help. The path forward is slower, harder work; proximity; humility; and real, reciprocal relationships.
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, Founder, Responsive FundraisingWriting Projects
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