Chicago gathered this week to mourn and honor the life of Rev. Jesse Jackson Sr., the longtime civil rights activist and political hopeful whose influence reshaped both grassroots organizing and national electoral politics. 

Thousands of mourners quietly streamed through the Rainbow/PUSH Coalition headquarters on the city’s South Side, where Jackson lay in repose, paying their respects to a man whose voice helped redefine Black political power in America. 

Among those who eulogized Jackson was Rev. Al Sharpton, who spoke emotionally about the final hours of Jackson’s life and their decades-long bond.

“About 2:30 in the morning, I received a text from Jesse Jackson Jr. that Reverend Jackson had passed,” Sharpton said during the memorial event. “A couple of hours later, his son Yusef called me and put me on speakerphone, and I prayed with the family as they stood around his bed. Even when you know someone is very ill, when the moment comes, you’re not prepared.” 

While Jackson’s moral leadership in the civil rights movement is widely known, speakers and attendees throughout the week emphasized another part of his legacy: his role as a political architect who expanded the boundaries of who could seek power in the United States.

Sharpton traced their relationship back nearly seven decades, recalling that he first met Jackson when he was just 12 years old, after being appointed youth director of Operation Breadbasket under Jackson’s leadership. 

“He was about 27. I was 13, and ever since then, for 69 years, we bonded,” Sharpton said. “He was a hard taskmaster, but he was more responsible than anyone for teaching me activism.”

Jackson’s presidential campaigns in 1984 and 1988 were watershed moments. At a time when Black candidates were rarely taken seriously on the national stage, Jackson mounted campaigns that were unapologetically ambitious. He won millions of votes, carried multiple states, and forced the Democratic Party to confront issues it had long sidelined, including economic inequality, voter suppression, labor rights, racial tensions and U.S. Jackson also influenced U.S. foreign policy towards Black and developing nations. He even coined the phrase "African American" from "Black American" to shift the focus from racial ("Black" or "colored") to a cultural and ethnic identity.

His Rainbow Coalition strategy brought together Black voters, working-class communities, young people, labor organizers, and marginalized groups across racial lines, a political framework that would later become standard but was radical at the time. 

By the end of the 1988 primary season, Jackson had finished second overall, winning 11 contests and earning nearly seven million votes. His campaigns laid critical groundwork for future generations of candidates and helped normalize the idea of Black presidential viability decades before it became reality.

Chicago was the foundation of Jackson’s political life. From the South Side, he built a national organizing machine that, much like its moniker (Windy City) suggests, blended protest with policy and moral pressure with electoral leverage. Rainbow/PUSH became a hub for voter registration drives, corporate accountability campaigns, and international human rights advocacy. He also often fought against the mostly white “machine” of Daley-era politics. 

Local and national leaders who attended the services noted that Jackson understood something many others did not: protest alone was not enough. Political participation—votes, campaigns, negotiations, and policy demands—was essential to sustaining civil rights gains.

Mayor Brandon Johnson and Rev. Al Sharpton were among those who reflected on Jackson’s insistence that Black communities engage power directly, even when the political system was hostile or dismissive. 

"Reverend Jackson meant so much to the people of the globe, but to me personally, was a mentor and a friend and a brother, and he will be forever missed,” Johnson told reporters just outside the doors of the service. “I'm grateful for his life and his legacy and the transformation that he has brought to the globe.” 

Jackson’s political career was not without controversy. Mourners acknowledged that he often ran ahead of public opinion, pushing conversations others were unwilling to have and entering political spaces where he was told he did not belong. 

That willingness to challenge party leadership, corporate interests, and U.S. foreign policy became a defining feature of his career. Through negotiations, boycotts, and diplomacy, Jackson positioned himself as both an agitator and a power broker, expanding the scope of Black political leadership beyond protest and symbolism. 

As funeral events concluded in Chicago and plans moved ahead for additional services in South Carolina and Washington, D.C., the tone throughout the week was one of responsibility as much as remembrance.

Jackson’s family and longtime allies emphasized that his work remains unfinished, particularly as the nation grapples with renewed attacks on voting rights, widening economic inequality, and persistent racial injustice.

The message that echoed through the services was clear: Jesse Jackson’s legacy was rooted in hope as action—organized, strategic, and unapologetically Black.

In the city that shaped him and that he helped transform, Chicago bid the leader farewell and reflected on his lifelong commitment to positioning Black people to believe in their power and use it to chanfe the world.