For generations, philanthropy has been a stabilizing force in moments of civic strain, moving resources where markets and government fall short—funding civil rights litigation when equality was contested, backing HIV/AIDS research and advocacy when public response lagged, and supporting recovery efforts after disasters like Hurricane Katrina.

Today, as the United States enters another volatile election cycle and democratic institutions face renewed pressure, that role is being tested in real time.

And precisely when it is most needed, philanthropy is failing to meet the moment—not because it lacks money, but because it lacks courage. 

Philanthropy commands over $1 trillion in assets in the U.S. alone, yet distributes just above the 5% legal minimum each year. At the same time, most funding remains restricted and risk-averse, with nearly 70% of nonprofits reporting that funders avoid bold or flexible investments. And all this at a time when, according to a recent report from the Center for Effective Philanthropy, 69% of nonprofits have reported funding cuts while 65% report increased demand for their services. 

Even as needs mount, the philanthropy sector behaves as if the greatest risk is to itself, while our communities and our democracy shoulder the consequences. 

The underlying problem is that fear—not imagination—still sets the terms, reinforcing systems that prioritize the safety of institutions and wealth over the well-being of communities, and control over partnership. 

In Minneapolis, Los Angeles, Philadelphia, and across the country, communities are carrying the weight of this moment. Local organizers and civic leaders are risking harassment, political targeting, violence, and censorship. They are defending voting rights, protecting vulnerable families, and holding fragile coalitions together.

Simply put, those with the fewest resources are bearing the greatest risk. The question before us is: how do we show up for them?

Communities already possess the shared understanding, deep relationships, vision, and wisdom required to thrive. What they are denied is resources and trust. This is where our courage comes into play.

Too often, philanthropy misjudges where the real risk lies. For grassroots leaders and activists, the risk is immediate and personal—their safety, their livelihoods, and their freedom. Yet inside our institutions, we behave as though the greater danger is to ourselves.

In practice, this has created a form of self-preserving philanthropy. We move slowly. We demand reporting. We avoid the issues most likely to provoke those in power. We prioritize insulating our endowments for a hypothetical future while others absorb the immediate consequences of action. But in a moment like this, safety for institutions often means exposure for communities.

To be clear, the philanthropy sector does face real risks: regulatory, political, reputational. But those stewarding the largest endowments are also the most protected. If courage means acting despite fear, then it is our responsibility to move through discomfort and not hide behind it.

So what does that courageous philanthropy require?

There are high-profile exceptions. Philanthropist MacKenzie Scott’s large, unrestricted gifts drew admiration not only for their scale but also for embodying a different posture: trust leaders, fund them generously, and step back. But her model is newsworthy precisely because it is unusual. The fact that trust-based, unrestricted giving is still treated as exceptional tells us how far the sector is from meeting this moment.

Unrestricted funding should be the baseline, not the breakthrough.

If those closest to injustice are also closest to the solutions, then philanthropy must be willing to shift the power dynamic and follow their lead. Too often, proximate leaders are treated as grantees to be managed rather than partners to be trusted—asked to prove themselves repeatedly within frameworks that were never built for them. If we truly believe communities hold the knowledge and vision to thrive, then our role is not to design a strategy but instead, to resource it.

That shift demands something deeper than flexible capital. It demands relationships.

Courageous philanthropy invests in people, not just plans. It places real bets on leaders and stands with them long enough for the work to unfold. It remains steady through backlash and is flexible when conditions shift. Sustaining this work requires more than project grants; it requires long-term partnership rooted in humility, not oversight.

Taken together, this is a posture shift. It requires staying when the path is unclear and funding through backlash rather than retreating from it. It asks us to align our risk tolerance with the risks organizers shoulder every day.

If philanthropy wants to be worthy of this moment—and this election cycle—we must do more. We must change how we show up. We must move closer, share power, and act with urgency.

History will not measure our sector’s success by the size of our endowments or the sophistication of our strategies. It will measure whether we put our capital and credibility on the line when democracy was under assault, or whether we protected our institutions while communities carried the risk alone.

Philanthropy means “love of humanity.” If that is true, the question before us is not whether we have the resources. It is whether we have the courage to use them—and the humility to change how we lead—now, as the country enters another defining test for democracy.