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Civil rights leader Rev. Jesse Jackson, who passed away on February 17, 2026, once praised Donald Trump at a 1999 event for his inclusivity and commitment to underserved communities, according to authenticated video footage that recently resurfaced.
The video clip, which has garnered millions of views across social media platforms including Instagram, X, and Facebook, shows Jackson introducing Trump at a January 14, 1999, gathering in New York for Jackson’s economic initiative called the Wall Street Project.
In his introduction, Jackson described Trump as “a friend” with a serious commitment to success “beyond argument.” He specifically noted Trump’s support for the Wall Street Project by providing space at 40 Wall Street, “which was to make a statement about our having a presence there.”
Jackson also acknowledged Trump’s involvement in his presidential campaigns in 1984 and 1988 when “many others thought it was either laughable or something to avoid.” He praised Trump for having “this sense of the curious, and a will to risk to make things better.”
“Aside from all of his style and his pizzazz, he’s a serious person who is an effective builder for the people,” Jackson said before introducing Trump to speak on “challenges and opportunities to embrace the underserved communities.”
The New York Times reported on the 1999 event but did not specifically mention Trump’s presence, possibly because other notable figures, including then-President Bill Clinton, were also in attendance. This wasn’t the first time Jackson and Trump had collaborated—C-SPAN footage confirms Trump spoke on a panel alongside Jackson at the Wall Street Project’s conference in January 1998 as well.
Getty Images archives contain dozens of photographs of the two men together, primarily from a 1988 Mike Tyson boxing match, indicating their paths crossed multiple times throughout the years before Trump entered politics.
While Trump did not formally begin his political career until his 2015 presidential campaign, he had floated the idea of running for president as early as 1987. Jackson, who remained a lifelong Democrat, would later become critical of Trump’s policies and presidency.
Following Trump’s 2016 election victory, Jackson wrote in an opinion piece for The Guardian: “He has a lot of reaching out to do. For the sake of the country and the world, I pray his arms are long enough. Yet, reaching out is not enough. He must also embrace and include those he has pushed away.”
The relationship between the two prominent figures illustrates the complex evolution of their public interactions over decades. The authenticity of the 1999 video clip has been verified, confirming that Jackson indeed praised Trump for his business acumen and support of initiatives aimed at underserved communities long before Trump’s controversial political career began.
The circulation of this historical footage following Jackson’s death offers a glimpse into their earlier relationship, which stands in stark contrast to the political divisions that would later emerge between the civil rights leader and the future president.
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10 Comments
Interesting to see this historical footage of Rev. Jackson praising Trump’s community outreach efforts. It provides useful context on their relationship at the time, beyond just the current political narratives.
Agreed, it’s important to examine these kinds of nuanced relationships, rather than just relying on partisan talking points.
The resurfacing of this footage is a useful reminder that political figures’ relationships and views can evolve over time. It’s worth looking at the full arc, not just isolated moments.
Exactly. People’s positions can shift, especially on complex issues. A more holistic perspective is needed to properly assess this kind of situation.
This is a complex issue with a lot of history. While Trump and Jackson had some points of alignment, their overall records and politics were quite different. It’s worth digging deeper to understand the full context.
Good point. Real-world relationships are often more complicated than the simplified versions we see in the media. Fact-checking and nuanced analysis are important here.
This raises some interesting questions about the nature of political alliances and how they can shift. It’s a complex topic that deserves careful, balanced examination.
Agreed. Oversimplifying these kinds of relationships often leads to a distorted understanding. Thoughtful analysis is required to really get at the nuances.
The footage provides a glimpse into a relationship that was more multifaceted than the current partisan narratives suggest. It’s a good reminder to look beyond surface-level portrayals.
Absolutely. Real-world political dynamics are rarely black and white. Digging into the details and historical context is crucial for a more accurate understanding.