Jeanette Taylor, the alderwoman of Chicago’s 20th Ward, first met the Rev. Jesse Jackson in 2012. At the time, she was an organizer with the Kenwood Oakland Community Organization, and her executive director insisted that she meet him. Taylor was nervous: She knew his national stature, his speeches, his mystique — and “sometimes when you know people for their work, you don’t think that you’ll ever get to meet them,” she told Capital B.

But Jackson, she said, was kind, funny, and empathetic. Their relationship deepened in 2015, during a hunger strike that Taylor helped to lead over the closure of Dyett High School. While city officials mocked the protesters, Taylor recalled, Jackson was one of the few pastors who offered them space to sleep and gather.

On Friday, Chicago will host a “people’s celebration” of Jackson, followed by a homegoing service on Saturday. The event will cap off a series of commemorations of the titan of U.S. politics, Civil Rights Movement leader, and Democratic Party power player who died in February at 84.

Jackson was a complicated figure who meant the world to so many Black Americans. He provided the first proof of concept that a Black presidential candidate could mobilize voters nationwide when he competed in Democratic primaries for president in the 1980s, a model that was adapted and modernized by the presidential campaigns of Barack Obama.

But in Chicago and other cities, Jackson is being celebrated not just as a charismatic leader and effective organizer, but as a man who nurtured, mentored, and developed multiple generations of Black leaders. 

Now, as people grieve, those who worked directly with Jackson are reflecting not only on the coalition he created as the founder of the human and civil rights organization Rainbow PUSH, but also on how he influenced them, where he came up short, and who will fill his shoes.

Taylor often drives by the Rainbow PUSH headquarters, not far from her office. 

Recently, she’s watched mourners gather there, people standing together to pay their respects to Jackson, who established the organization in 1996, and led it until 2023

“It’s just — it’s heartbreaking,” said Taylor, 50. “It’s surreal.”

“There was already a hole when he got sick,” she added, referring to Jackson’s health problems in recent years. “But we just thought that he would bounce back. Nobody wants their heroes to die. We want them to live forever.”

Jackson’s influence on leaders in Washington, D.C.

David Johns, 44, is the executive director of the National Black Justice Collective, a Washington, D.C.-based group that focuses on the needs and experiences of Black LGBTQ Americans. 

He met Jackson around 2007. What Johns remembers most is that Jackson made room for him and other young leaders. At monthly gatherings of Black-led organizations in Washington, when Jackson attended, he ensured that younger advocates were heard — “not in a performative way,” Johns said, “but to ensure that our perspectives were included in not only the conversation, but also the analysis and the subsequent action.”

Johns often returns to Jackson’s 1984 Democratic National Convention speech, in which he described the U.S. as a richly textured piece of fabric.

“The white, the Hispanic, the Black, the Arab, the Jew, the woman, the Native American, the small farmer, the businessperson, the environmentalist, the peace activist, the young, the old, the lesbian, the gay, and the disabled make up the American quilt,” declared Jackson, credited as the first person to say “gay” or “lesbian” in a major convention speech.

Johns told Capital B, “I’ve always appreciated, in my work, that there should be much more room for intersectional approaches to how we all live this thing called life.”

Jackson’s influence in South Carolina, his home state

The remains of the late Rev. Jesse Jackson are brought to the South Carolina State House via a caisson on March 2. (Joshua Boucher/The State/Tribune News Service via Getty Images)

Those who encountered Jackson’s movement in the 1980s saw the roots of the organizing that would become the “rainbow coalition.”

Lawrence Moore, 70, who lives in Columbia, South Carolina, and is the chair of the social justice nonprofit Carolina for All Education Foundation, first met Jackson in 1976, as a college student, when Jackson was eyeing the White House. By 1988, Moore was helping to coordinate Jackson’s presidential campaign efforts in the Palmetto State.

“Jackson created more of a movement, where people believe in a vision,” Moore said of Rainbow PUSH, describing what was less a political campaign than an unbreakable affiliation. “I’ve never seen a ‘former’ Jackson supporter. Everybody I know who supports Jackson, it’s a lifetime thing.”

On Monday, Moore stood among thousands who had gathered in Columbia to honor Jackson in his home state. A procession marched a mile from the funeral home to the State House. Andrew Young, an early civil rights leader who once served as executive director of the Southern Christian Leadership Conference, was there, along with other longtime allies.

Moore told Capital B that Rainbow PUSH built something lasting — a “family, a nation of people who believe in humanity and believe in one another.”

Jackson’s influence on Obama

When Obama launched his presidential campaign in 2007, he followed some of Jackson’s blueprint for building power by explicitly courting a multiracial, cross-movement alliance.

Obama’s campaign modernized the strategy, pairing it with digital organizing and a new generation of activists. But the underlying logic was familiar: join together Black voters, young people, labor activists, immigrants, LGBTQ Americans, progressive white Americans, and more under a shared political narrative.

At times, the relationship frayed, including in 2008, when Jackson made crude remarks about Obama during his presidential campaign. Obama accepted Jackson’s apology, brushing aside the episode as the race intensified.

“He was human,” Taylor said. “But you can’t deny that he stood up for Black children, Black people, Black communities.”

Months later, when the Illinois Democrat won the White House and delivered his victory speech in Chicago’s Grant Park, Jackson stood in the crowd, visibly moved and emotional — a civil rights veteran watching a barrier fall after decades of struggle.

Can Jackson’s movement survive without him?

Jackson still appears at the top of the masthead of Rainbow PUSH, on the organization’s website, listed as founder emeritus. Under him appears one of his sons, Yusef D. Jackson, listed as the chief operating officer of the organization.

In a statement issued the day Jackson died, Rainbow PUSH said, “His legacy will continue to inspire future generations through the tireless, dedicated work of the Rainbow PUSH Coalition, an organization rooted in the progressive fight for social change.”

But on the day of the Chicago funeral, the question many who knew him are now asking is what it will take to sustain the organization’s work.

Ameshia Cross, a Chicago native and political analyst, grew up seeing Rainbow PUSH as a fixture of South Side life. “You can’t not know about Rainbow PUSH in Chicago,” she told Capital B. As an adult, she later volunteered and worked with the organization, hosting Affordable Care Act enrollment drives and partnering on education initiatives.

To Cross, the coalition’s mission feels as relevant as ever.

“What we saw even before this administration was a pitting of Black Americans and Latinos against each other,” Cross said. “I see Rainbow PUSH as a vision of unification, one that stands as a beacon and a pillar,” she added. 

Cross recalled being a college student when Jackson pushed her to speak before thousands of people at a Rainbow PUSH event.

“This was a man who saw the importance of me being encouraged to speak in front of thousands of people,” she said. “It mattered to me to have him look at me as somebody who could do something.”

Moore said that those who want to keep Jackson’s legacy alive must act. “We the people, now, need to make sure that we stand up,” he said.

Back in Chicago, Taylor has been thinking about that responsibility, too.

“I’m just praying that we take Jackson’s lessons and apply them to our own lives, and create more Jacksons — more people who will stand up for our communities and do what’s right, even when it’s uncomfortable,” she said. “What would he tell us? To keep hope alive.”

Brandon Tensley is Capital B's national politics reporter.