Did Jesse Jackson like Donald Trump? They once collaborated
- - Did Jesse Jackson like Donald Trump? They once collaborated
Kinsey Crowley, USA TODAYFebruary 18, 2026 at 1:45 AM
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Did Jesse Jackson like Donald Trump? They once collaborated
Famed civil rights activist Rev. Jesse Jackson died at age 84 on Feb. 17.
"It is with profound sadness that we announce the passing of Civil Rights leader and founder of the Rainbow PUSH Coalition, the Honorable Rev. Jesse Louis Jackson Sr.," the organization said in a statement. "He died peacefully on Tuesday morning, surrounded by his family."
Jackson had a storied public career, from advocating alongside Martin Luther King Jr. to running to be the Democratic presidential nominee twice to receiving the Presidential Medal of Freedom.
He has long fought to broaden the Democratic umbrella, but he crossed paths with President Donald Trump long before the New York businessman became the face of the Republican Party. In fact, they once considered themselves friends. Here is what to know:
More: Jesse Jackson, towering icon of civil rights, dies following lengthy illness
1 / 38See Jesse Jackson mingle with athletes and celebrities through the yearsSinger Aretha Franklin sits court side with Reverend Jesse Jackson during the NBA basketball game between the Detroit Pistons and Miami Heat in Auburn Hills, Michigan Feb. 11, 2011.Jesse Jackson once collaborated with Trump before endorsing his opponents
Before Trump got into politics, he donated some of his office space in Manhattan to Jackson's Rainbow/PUSH Coalition. The New York Times reported in 1997 that Jackson and his organization were headed to Wall Street to put pressure on corporations to advance Black and minority employees within their companies.
In a 1999 press conference about the project, Jackson called Trump a "friend" and "in terms of reaching out and being inclusive, he's done that, too," before introducing Trump to speak.
"Jesse started off by saying, 'most of the wealth in this country is in the hands of a few.' And I thought to myself: is that a bad thing?" Trump said at the press conference prompting laughs. He noted how Jackson had asked for the office space for free. "He's a very tough negotiator ... Nah, he's a terrific guy. We love him, and I'm here for him."
Fast forward to the 2016 election, Jackson endorsed Democratic opponent Hillary Clinton. Talking to Bloomberg Television about his history with Trump at the Democratic National Convention in 2016, Jackson called him "affable and social," but recalled how things started to change when Trump promoted the birther movement. Jackson was critical of Trump's campaign messages on foreign policy, immigration and repealing Obamacare.
"These ideas are not just conservative, they are somewhat way off the main line. They could destabilize the country," he told Bloomberg. He also declined to weigh in on whether Trump is racist, saying he didn't want to make the campaign about "branding."
In 2020, Jackson endorsed Bernie Sanders in the Democratic primary. Jackson was honored as a civil rights icon at the 2024 Democratic National Convention, appearing on stage in a wheelchair and receiving a standing ovation.
What did Donald Trump say about Jesse Jackson's death?
Trump posted on Truth Social on Feb. 17, discussing their previous relationship and arguing that it countered accusations that he is racist.
"I knew him well, long before becoming president. He was a good man, with lots of personality, grit, and 'street smarts.' He was very gregarious - Someone who truly loved people!" the post read.
"He loved his family greatly, and to them I send my deepest sympathies and condolences. Jesse will be missed!"
Did Jesse Jackson really dislike Obama?
Trump's Truth Social post also said Jackson helped elect former President Barack Obama, "a man who Jesse could not stand."
Jackson, a two-time presidential hopeful himself, publicly supported Obama. But during the 2008 campaign, Jackson made some critical comments about Obama that he later apologized for, saying he thought he was off the record.
When Obama won that election, Jackson cried, as recounted by a CBS News reporter who interviewed him the morning after.
"We are a better America today," Jackson told CBS in 2008. "America is a work in progress, and last night we saw that that work in a most magnificent way expressed."
Contributing: Reuters; USA TODAY's Trevor Hughes, Rachel Barber
Kinsey Crowley is the Trump Connect reporter for the USA TODAY Network. Reach her at [email protected]. Follow her on X (Twitter), Bluesky and TikTok.
This article originally appeared on USA TODAY: Donald Trump's post on Jesse Jackson death mentions past relationship
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