Introducing Rev. Jesse Jackson Sr. as a Founding Architect of Grassroots Philanthropy
On February 17, 2026, America lost one of its most consequential voices. Rev. Jesse Louis Jackson Sr. — preacher, organizer, two-time presidential candidate, and founder of the Rainbow PUSH Coalition — died peacefully at his home in Chicago at the age of 84. The tributes poured in immediately, as they should. But this series is not simply a eulogy. It is a reclamation.
Because what most tributes will not tell you — what the obituaries rarely capture — is that Rev. Jesse Jackson Sr. was one of the earliest and most sophisticated practitioners of what we now call grassroots philanthropy. Decades before the nonprofit sector had a playbook, before GoFundMe existed, before impact investing had a name, Jackson was building the architecture of community-powered giving, movement-funded advocacy, and coalition-driven change.
He was doing it from pulpits and protest lines, from convention stages and community halls. And the sector is still catching up to him.
“He didn’t just keep hope alive. He kept resources alive — and he taught communities that they were the resource.”
A Fresh Lens on a Familiar Legacy
When we think of Jesse Jackson Sr., we think of the man at the balcony of the Lorraine Motel. We think of the 1988 Democratic National Convention, the booming voice, the soaring rhetoric. We think of “Keep Hope Alive.”
What we rarely think about — and what this series is here to argue — is the philanthropic infrastructure he was quietly, persistently, brilliantly building beneath all of it. The fundraising model. The coalition architecture. The community-as-donor philosophy. The donor retention strategy hiding in plain sight inside his most famous slogan.
Over the course of four articles, we will walk through five pillars of Rev. Jackson’s philanthropic legacy, and trace how each one maps onto the principles that drive the most successful nonprofit and fundraising work today. We will close by looking at who carries this forward — and what it means for all of us who work at the intersection of community, generosity, and change.
Why This Matters Now
The philanthropic sector is at an inflection point. Institutional donors are pulling back. DEI funding is under pressure. Grassroots movements are scrambling for resources. The old models of top-down philanthropy are straining under the weight of a world that has changed faster than the sector’s structures.
Into this moment steps the memory of a man who never waited for institutional permission to build something meaningful. Rev. Jesse Jackson Sr. understood — decades before the sector articulated it — that the most durable philanthropy is the kind that comes from the community itself. That ordinary people, pooling extraordinary conviction, are not just beneficiaries of generosity. They are its source.
That idea is not nostalgic. It is the answer to the questions the sector is wrestling with right now.
The Foundation: The Church as Philanthropic Infrastructure
Before we can understand what Jackson built, we must understand what he stood on. The Black church was already the most sophisticated philanthropic institution in America. It collected resources weekly. It distributed them locally. It mobilized people around shared values. It was, in the truest sense, a community foundation with a congregation.
Jackson understood this instinctively. He did not build from scratch — he scaled what already existed. His early work with Operation Breadbasket was rooted in the church’s economic leverage: organized congregations deciding, as a body, where to invest their collective purchasing power and where to withhold it.
That instinct — meet people where their generosity already lives — is the first and perhaps most enduring lesson for modern fundraisers. The most successful campaigns today, whether a capital campaign for a community hospital or a crowdfunding surge for disaster relief, succeed because they tap into existing communities of trust. Rev. Jackson understood that principle before it had a name.
“The most durable philanthropy comes from the community itself. Rev. Jackson knew this before the sector had language for it.”
What’s Coming in This Series
In Part Two, we explore how Rev. Jackson’s Operation Breadbasket and the founding of PUSH pioneered what we now call economic philanthropy — and how his presidential campaigns became the first large-scale proof of concept for small-donor fundraising.
In Part Three, we examine the Rainbow Coalition as a masterclass in donor diversification, and unpack why “Keep Hope Alive” was one of the most effective donor retention strategies in American history.
And in Part Four — published in honor of his funeral services in March — we look at who carries this legacy forward today, and what it means for every one of us who believes in the power of community to change the world.
The sector is still catching up to Rev. Jesse Jackson Sr. It is time we named that — and learned from it.
Fondly,
Monique
Rest in power, Rev. Jesse Louis Jackson Sr. | October 8, 1941 – February 17, 2026
This is Part 1 of 4 in the “Honoring Rev. Jesse Jackson Sr.” series. Next: Part Two — The Economics of Justice
