News of the Rev. Jesse Jackson’s health struggles has stirred many. It has me praying. And it has me remembering the hard lessons he taught, shaped in the trenches of our people’s ongoing fight for freedom.
Look around the world, and it is easy to find charismatic voices rising amid liberation movements. Black America has been blessed with such figures across generations — perhaps because we have been cursed with a freedom struggle that never really ends.
Through all that pain and hope, for nearly half a century, our most consequential and transformative leader has been the Rev. Jesse Louis Jackson, Sr.
Some dismiss his leadership as style over substance. “Keep Hope Alive!” they say. Sometimes with reverence. Sometimes half-mockingly. When I hear that latter tone, I’m reminded how privileged a life one must lead to think hope is just a slogan and not sacred labor.
They don’t understand the discipline it takes to help a people — or a nation — maintain hope in the face of adversity.
Last summer, at the Democratic National Convention in Chicago, Jackson invited me to join him and his family in their box. I sat beside my old mentor and friend, holding his hand as Vice President Kamala Harris accepted the nomination for president.
The symbolism of the location for the night was unmistakable. We were in the city that sent Barack Obama to the White House. But we were also in the city that decades before empowered Jackson to show America the question was no longer whether it would elect a Black president but when.
He demonstrated that truth not only through his presidential campaigns in 1984 and 1988 — campaigns that broke ceilings and forged coalitions but through the generations of leaders he encouraged and inspired.
The year after his last presidential run, Virginia elected its first Black governor, L. Douglas Wilder. New York elected its first Black mayor, David Dinkins. Both publicly named Jackson as someone who helped make their possibilities real.
And just this past January, at Chicago’s Martin Luther King Day celebration, Jackson’s impact was visible from City Hall to the state Capitol — a reminder that his legacy is not nostalgia, but political infrastructure.
A decade earlier, I was one of the few Black partners at any Silicon Valley venture-capital firm. I was told there had only been 36 Black men to hold such positions in the history of the Valley.
Then Jackson showed up. He stood before the boards of some of the largest technology companies in the world and told them plainly they needed to open their doors — not because it was charity, but because it was smart business.
Firms that had never once hired African American investors began doing so soon after. I asked one top executive if Jackson’s public and private confrontations of their leaders had influenced that shift. He didn’t hesitate: “He’s right. We need to change.”
That’s the core of Jackson’s leadership — not just breaking barriers himself, but inspiring others to do so. He helped ordinary people see themselves as leaders and compelled those with resources to recognize their responsibility.
In doing so, he became a beacon of hope and taught others to be beacons themselves.
He continues to model that courageous hope even now. His leadership lessons still empower others to help transform our world for the better.
In 2010, Jackson and I led a delegation of African American leaders to Senegal to mark the 50th anniversary of its independence. Nearly every head of state on the continent was present, including some notorious for human rights abuses.
I froze, unsure how to engage them. Jackson did not. He walked forward, shaking their hands and hugging each with warmth.
Later I pulled him aside. “I don’t see how I can do that,” I told him.
He looked me in the eye. “Someday somebody’s parent or wife will call me,” he said. “A soldier. A missionary. A businessperson. And they will want help getting his or her loved one free. How will I be able to convince that president to free them if he doesn’t know that I love and respect him as my brother?”
It was a lesson in diplomacy that changed everything for me. But it was more than diplomacy. It was a Christian pastor living out Jesus’s commandment to “love your neighbor as yourself.”
This wasn’t sentimentality. It was strategy. Integrity. Faith turned into action.
I stepped back into that room and greeted every leader there without judgment, without reservation. Not because each had earned it, but because transformation requires it.
Because hope demands it. Because, as Jackson taught, the work is helping each other become our best and never giving up on the faith that each of us can do better tomorrow than we did yesterday.
As Jackson fights to regain his strength in Chicago, his lesson stands: hope is not a feeling you wait for. It is a discipline you practice.
And he is still teaching us — by living it — that no matter how dark the moment may be, we must keep hope alive by continuing to fight for a better day.
Ben Jealous is a professor of practice at the University of Pennsylvania and former national president and CEO of the NAACP.