Jesse Jackson Changed Chicago. And It Changed Him.

Mr. Jackson, who spent much of his life in the city, died at his home there on Tuesday. “He ushered in new politics in Chicago,” one longtime organizer said.

In 1964, a young Jesse Jackson spurned a chance to study law at Duke University and headed north instead, enrolling in a seminary on the South Side of Chicago.

He later dropped out, just months shy of graduation. But Mr. Jackson found a home in Chicago, making it his family and political power base of the next six decades.

It was in Chicago where Mr. Jackson disrupted the city’s famed political machine, controlled by the white establishment and the Daley family, who held the mayor’s office for generations. Mr. Jackson pushed Chicago politics to the left, organizing boycotts of local businesses when they refused to stock goods from Black contractors or hire Black workers. From the South Side headquarters of the Rainbow PUSH Coalition, he gave local, state and national political candidates a valuable stage, even as his own political power dwindled with age.

And he loudly advocated on behalf of the Black community, the working class and the homeless, often irking local officials along the way.

Even after the Daleys had stepped away from City Hall, Mr. Jackson remained a regular presence on its fifth floor, where Chicago mayors welcomed him as an ally, negotiator, elder statesman and sometimes foe.

“He wanted access to the fifth floor, and he had it,” Rahm Emanuel, the mayor from 2011 to 2019, said on Tuesday. “He was simultaneously confrontational, challenging, but collaborative and cooperative. He had all those tools in his toolbox.”

At the Jackson family home on the South Side, where Mr. Jackson died early Tuesday, his eldest daughter, Santita, said that in Chicago, Mr. Jackson learned “great lessons” and forged relationships, however complicated, with the city’s leaders.

“Chicago welcomed him, and what he wanted to do for Chicago was make it a welcoming place for everybody,” she said. “He worked to do that throughout his life.”

It was in Chicago that Mr. Jackson, at 24, was chosen to lead a chapter of the Southern Christian Leadership Conference’s Operation Breadbasket, a national economic development campaign that used boycotts to pressure white businesses to hire Black workers and to purchase goods and services from Black contractors. For too long, Mr. Jackson would say, residents of Black neighborhoods in Chicago had faithfully voted for Democratic candidates without exercising their own considerable power as a voting bloc.

Local officials in Chicago clashed with Mr. Jackson so often that people in his inner circle sometimes said, half-jokingly, that he was more popular outside the city than within it.

“His most important contribution was to be part of a movement that helped to break the Black community away from the old Daley machine,” said Don Rose, a political consultant who worked with Mr. Jackson regularly for decades. “He was important in the city’s politics even though he never really won anything.”

Mr. Rose recalled the pressure that Mr. Jackson and his organization inflicted on Richard J. Daley, who served as mayor of Chicago for 21 years. At the 1972 Democratic National Convention, Mr. Jackson helped seat an insurgent delegation in a blow to Mr. Daley.

Later that year, Mr. Jackson organized voter registration drives and worked to convince Black voters to cast their ballots for a Republican over Edward V. Hanrahan, a Democrat who was supported by Mr. Daley but unpopular with Black voters, in a critical state attorney’s race.

“He ushered in new politics in Chicago,” said Hermene Hartman, an organizer and close friend of Mr. Jackson’s. “He grew Black businesses, he grew Black representation.”

Mr. Jackson’s failed presidential campaigns in 1984 and 1988 were widely seen as having paved the way for Barack Obama’s successful presidential bid in 2008.

The Rev. Michael Pfleger, pastor of St. Sabina Church on Chicago’s South Side, had been close with Mr. Jackson since the 1970s.

“He was really serious about the concept of a rainbow coalition, which I think he got from his mentor, Dr. King, who really believed that until we come together as Black, white and brown, we’re never going to win,” Father Pfleger said. “He never gave up on that.”

At the Rainbow PUSH Coalition, Mr. Jackson still presided over candidate forums during mayoral campaigns in recent years. In 2020, he showed up in Kenosha, Wis., after a high-profile police shooting, and encouraged younger activists, though they saw him as more of a legend than a leader.

In 2023, Mr. Jackson stepped down as the head of Rainbow PUSH but remained a regular presence at political rallies, campaign events, conventions and protests in Chicago.

In his final years, when Mr. Jackson’s health was in decline from Parkinson’s disease, he still attended events in a wheelchair, his voice that was once famed for its oratory reduced to a whisper.

Leigh Giangreco and Robert Chiarito contributed reporting.

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