Jesse Jackson Dies at 84: His Shocking Relationship with Donald Trump Revealed

The passing of civil rights leader Jesse Jackson has reopened one of the most surprising political relationships of the last half-century — his long, complicated bond with President Donald Trump. Their story begins in the New York of the 1980s, runs through Trump’s business empire, touches the early days of Jackson’s presidential ambitions, and ends with Jackson becoming one of Trump’s fiercest critics before the two men exchanged final, respectful words decades later.

It’s a relationship that says as much about America’s transformations as it does about the two men.

In the hours after Jackson’s death at 84, President Trump reacted with warmth and a pointed reminder of their shared history.

“He was a good man, with personality, grit, and street smarts,” Trump wrote on Truth Social. “Someone who truly loved people. I was always happy to help Jesse along the way — no matter what the Radical Left says about me.”

It was a moment of unexpected reconciliation. And it stunned many Americans who only knew the pair as political combatants in the Trump era.

Decades earlier, Jackson and Trump often crossed paths in New York’s media and business world. Jackson led Operation PUSH and later the Rainbow PUSH Coalition, pushing corporations to hire and invest in minority communities. Trump was building skyscrapers, casinos, and a national brand.

The two weren’t political allies. But they weren’t enemies either.

Jackson, a two-time Democratic presidential candidate, once said Trump treated his campaigns with respect when many in the establishment mocked them.

“When others laughed or ignored us, Donald Trump showed up,” Jackson said during a speech in the 1990s. “He was curious. He was willing to take risks. And he listened.”

Their shared presence at boxing matches in Atlantic City — glitzy Trump Plaza events drawing stars, politicians, and moguls — symbolized that odd overlap between civil rights activism and Manhattan celebrity culture.

The turning point came in early 1999, when Trump appeared at Jackson’s Wall Street Project conference. Jackson publicly praised Trump for donating office space at 40 Wall Street and supporting minority business initiatives.

“He’s a terrific guy. We love him, and I’m here for him,” Trump said to the crowd.

Jackson reciprocated with gratitude. The clip would become political dynamite years later when Trump’s critics accused him of racism.

Trump used that moment to argue something simple: his record with minority communities pre-politics was real, long-standing, and on video.

The relationship collapsed the moment Trump entered partisan politics.

Jackson became one of his sharpest detractors during the 2016 election and throughout Trump’s presidency. He denounced Trump’s messaging and accused him of reopening old wounds.

“The idea of making America great again reopens the wounds in America’s immoral foundation,” Jackson said after Trump’s 2016 win.

He argued that Trump’s policies hurt the communities Jackson fought for. He delivered personal criticisms too, at one point saying, “Jesus would not qualify to enter Trump’s America.”

By Trump’s first term, their dynamic had shifted from friendly New York acquaintances to representatives of two competing visions for the country.

Trump consistently rejected accusations of racism — and often pointed to his old ties with Jackson as proof.

“I’m the least racist person you have ever interviewed,” he told reporters in 2018. He reminded the press that Jackson once praised him publicly for helping minority businesses get a foothold in finance and real estate.

His supporters shared the 1999 video widely during Trump’s campaigns, describing it as proof that the media’s narrative didn’t match history.

Their relationship, from its cordial beginnings to its later political flameouts, mirrors the transformation of American politics itself.

In the 1980s and 1990s, business leaders and civil rights figures could support each other occasionally despite ideological differences. By the time Trump became president, the political climate had hardened. The old lines of cooperation had vanished. Every relationship became partisan.

Yet Trump’s tribute in 2026 shows that the personal history between the two men never fully disappeared.

“Jesse had heart,” one longtime Trump associate told us. “They disagreed in the end. But Trump never forgot the guy he used to sit with at fights in Atlantic City.”

The story of Donald Trump and Jesse Jackson is not just a political biography. It’s a chronicle of America’s shifting eras — from New York’s golden age to a polarized nation and finally to a moment of reflection after Jackson’s death.

And in that story, Trump’s final words about Jackson stand out.

“He loved people,” the president said. “And I always respected that about him.”