Trump remembers Jesse Jackson as 'good man,' 'force of nature'
The Unlikely Alliance: Understanding the Jesse Jackson-Donald Trump Relationship
In the hours following the passing of the Reverend Jesse Jackson at age 84, a remarkable thing happened. President Donald Trump took to Truth Social to offer a tribute that was equal parts memorial, defense of his own record, and characteristically pointed political commentary . "Jesse was a force of nature like few others before him," Trump wrote. "I knew him well, long before becoming President. He was a good man, with lots of personality, grit, and 'street smarts'" .
For those who have watched American politics over the past decade, this moment of presidential praise for a civil rights icon might have seemed jarring. After all, Jackson had become one of Trump's most vocal critics during his presidency, condemning his immigration policies and rhetoric as "dangerous, divisive, and diversionary". Yet their relationship stretches back nearly four decades a complex history that defies simple categorization and offers valuable lessons about political alliances, personal relationships, and the nature of public service.
From a conservative perspective, the Jackson-Trump relationship illuminates something important: the difference between transactional politics and transformational change, and the enduring value of engaging across ideological lines even when profound disagreements remain.
The New York Years: When Worlds Collided
To understand how a Manhattan real estate developer and a civil rights leader from the Jim Crow South developed any kind of relationship, one must understand the New York of the 1980s. It was a city of overlapping elite circles—business, media, entertainment, and politics where figures like Trump and Jackson inevitably crossed paths .
Jackson was then at the height of his national influence, having run for the Democratic presidential nomination in 1984 and gearing up for another bid in 1988. Trump, meanwhile, was ascending as a real estate mogul whose name was becoming synonymous with luxury and ambition. They attended the same high-profile events, including heavyweight championship fights at Trump Plaza in Atlantic City in 1988, 1989, and 1991—glitzy, televised spectacles that drew politicians, celebrities, and business leaders together .
Jackson later recalled that Trump took his presidential campaigns seriously when many in the establishment dismissed them. "When many others thought it was either laughable or something to avoid, he came to our business meeting here in New York because he has this sense of the curious and the will to risk to make things better," Jackson said .
This is a point conservatives might appreciate: Trump, whatever one thinks of his style, has never been afraid to engage with figures outside his immediate orbit. He showed respect for Jackson's ambition and his message at a time when doing so offered no obvious political advantage for a man who was then a Democrat.
The 40 Wall Street Decision: More Than Real Estate
The most tangible evidence of this early relationship came in 1997, when Trump made a decision that would become a footnote in both men's histories but a telling one. He announced he would donate office space to Jackson's Rainbow PUSH Coalition at 40 Wall Street, a building he was renovating .
This was not a small gesture. The Wall Street Project, Jackson's initiative to expand minority access to corporate America and financial markets, needed a physical presence in the heart of New York's financial district. Trump provided it for years, at no cost.
At the January 1998 conference marking the opening of the space, the dynamic between the two men was on full display. Trump, with his characteristic blend of self-deprecation and self-promotion, joked about Jackson's negotiating skills. "He's a very tough negotiator when it came to rent, I wanna tell you that. This man is definitely setting a new standard for paying low rent," Trump told the panel. "I said, Come on, Jesse, you gotta give me something. He said nothing. I said, Alright, what the heck. So he's tough" .
Jackson, in turn, praised Trump's seriousness of purpose. "One can miss his seriousness and his commitment, for his success is beyond argument," Jackson said. He added that Trump possessed a "sense of the curious and the will to risk to make things better" .
From a conservative perspective, this exchange reveals something often missing from today's hyper-partisan environment: the ability to acknowledge good faith efforts across political divides. Trump, a businessman, was supporting an organization dedicated to expanding economic opportunity in minority communities. Jackson, a civil rights leader, was willing to accept help from a source outside his usual political coalition. Both understood that progress on issues like minority business development required partners wherever they could be found.
The 1999 Wall Street Project Conference: A Moment of Praise
The relationship reached perhaps its warmest moment in January 1999, when Jackson invited Trump to speak at the Rainbow PUSH Coalition's Wall Street Project conference. There, Jackson introduced Trump warmly and again thanked him for providing the office space at 40 Wall Street, which he said was "to make a statement about our having a presence there" .
Trump, for his part, praised Jackson as "a terrific guy" and declared, "We love him and I'm here for him" . He spoke about his record as a builder and employer, pointing to his construction projects as creating jobs for large numbers of minority workers. He argued that expanding access to capital and opportunity in urban communities was both good business and good policy .
This moment captured on video and later circulated by Trump supporters during his presidential campaigns represents a high-water mark in their relationship. It also serves as a useful corrective to the simplistic narrative that Trump has always been persona non grata in the civil rights community. Jackson, no naif when it came to assessing political figures, saw enough in Trump to share a stage with him and offer public praise.
The Partisan Turn: When Politics Pulled Them Apart
If the story ended there, it would be a pleasant tale of cross-cultural cooperation in the spirit of colorblind opportunity. But politics, as it so often does, intervened.
When Trump launched his presidential bid in 2016 as a Republican, the dynamic shifted dramatically. Jackson, a lifelong Democrat who had twice sought the party's nomination, became a fierce critic. He condemned the tone and substance of Trump's rhetoric, particularly on immigration and race .
In the days after Trump's 2016 victory, Jackson did not mince words. "The idea of making America great again reopens the wounds in America's immoral foundation, born in sin, and shaped in inequity," he said . He warned of a "tug of war for the soul of America" and criticized Trump personally, saying, "Trump says you must be able to speak the language of English, [be] qualified, and have a job skill. Jesus would not qualify to come in Trump's country" .
By 2019, Jackson was describing Trump's attacks on minority lawmakers as fueling white nationalist extremism . The man he had once praised for his "sense of curiosity" and "will to make things better" had become, in Jackson's view, a threat to the communities he had spent his life advocating for.
For conservatives, this turn is both understandable and disappointing. Understandable because Jackson was, after all, a man of the Left who had built his career within the Democratic Party. Disappointing because it suggests that the personal relationships and cooperative efforts of the 1990s could not survive the partisan pressures of the 2010s. The office space at 40 Wall Street, the friendly introductions, the shared laughter about rent negotiations—all of it was washed away by the tidal wave of political polarization.
Trump's Defense: A Record to Stand On
Throughout his political career, Trump has faced accusations of racism charges he has consistently denied. And in his tribute to Jackson following the civil rights leader's death, Trump used their history together as part of his defense.
"Despite the fact that I am falsely and consistently called a Racist by the Scoundrels and Lunatics on the Radical Left, Democrats ALL, it was always my pleasure to help Jesse along the way," Trump wrote. He then enumerated specific actions he had taken: providing office space for the Rainbow Coalition "for years" at 40 Wall Street; responding to Jackson's request for help in passing criminal justice reform; securing long-term funding for Historically Black Colleges and Universities; and supporting Opportunity Zones, which he called "the single most successful economic development package yet approved for Black business men/women".
From a conservative perspective, this is not mere self-defense it is a legitimate point about results. Whatever one thinks of Trump's rhetoric, his administration did achieve significant policy outcomes that benefited minority communities. The First Step Act represented the most substantial criminal justice reform in a generation. Opportunity Zones have channeled billions in investment to distressed communities. HBCUs received unprecedented federal support.
Jackson, to his credit, had advocated for all of these things. And Trump, to his credit, delivered on them. The relationship between the two men, whatever its later strains, had produced tangible results.
The Obama Complication
No discussion of Jackson and Trump would be complete without addressing the complicated figure of Barack Obama. In his tribute to Jackson, Trump inserted a pointed observation: Jackson "had much to do with the Election, without acknowledgment or credit, of Barack Hussein Obama, a man who Jesse could not stand".
This was not mere mischief-making. There is a genuine historical point here. Jackson's presidential campaigns in 1984 and 1988 laid much of the groundwork for Obama's historic 2008 victory. Jackson expanded the Democratic electorate, built multiracial coalitions, and demonstrated that a Black candidate could compete for the presidency . Yet the relationship between Jackson and Obama was strained. In 2008, Jackson was caught on a hot mic saying he wanted to "cut [Obama's] nuts off" for what Jackson perceived as the candidate talking down to Black Americans.
For conservatives, this episode illustrates something important about the civil rights establishment and Democratic Party politics. The relationship between generations of Black leadership is more complex than the unified front presented to the public. Personal rivalries, policy disagreements, and competing visions all exist beneath the surface.
Lessons for Conservatives
What should conservatives take away from the Jackson-Trump relationship?
First, engagement matters. Trump's willingness to provide office space and appear at Rainbow PUSH events did not transform Jackson into a Republican, nor should it have. But it did create channels of communication and cooperation that eventually produced policy outcomes conservatives can be proud of. The First Step Act and Opportunity Zones were not gifts to the Left; they were conservative reforms that addressed real problems in ways consistent with conservative principles.
Second, personal relationships can survive political disagreements but only just. The friendship between Jackson and Trump, such as it was, could not withstand the intensity of contemporary partisan conflict. This is a loss. When political opponents can no longer share a stage or acknowledge each other's good faith, the country is diminished.
Third, results matter more than rhetoric. Jackson praised Trump in the 1990s for his willingness to engage. Trump, in turn, delivered policies Jackson had long advocated. The rhetoric of the 2016 campaign and the Trump presidency undeniably caused pain to many, including Jackson. But the policy record deserves honest assessment.
Finally, the Jackson-Trump relationship reminds us that American politics is not always as simple as the cable news narratives suggest. A real estate developer who would become a Republican president and a civil rights leader who would become his critic once found common ground. That ground was not vast it was a few thousand square feet of office space at 40 Wall Street. But it was enough to produce something of value.
In his final tribute to Jackson, Trump wrote that the civil rights leader "loved his family greatly, and to them I send my deepest sympathies and condolences. Jesse will be missed!". Whatever their political differences, whatever the strains of the Trump presidency, that sentiment stands as a testament to a relationship that spanned nearly four decades and to the possibility, however fragile, of finding common purpose across the divides that separate us.