Twice in the 1980s, Jackson ran for the Democratic presidential nomination, losing out both times, but not without having a major impact on the party's politics.
During this time, Jackson got to know Trump, then a real estate mogul, and the two were pictured together at boxing events.
Trump's initial foray into politics - he explored the idea of running for president on the Reform Party ticket - didn't go anywhere, but Jackson offered positive remarks about him, praising him for his business record and willingness to engage with minority communities.
When Trump decided to run for president in 2015, he used Jackson's words of praise to prove he wasn't racist. By then their relationship had cooled off and Jackson became a vocal critic, warning that Trump's rhetoric "seeded these clouds" of division and fear.
In 2016, Jackson told BBC Radio 4 that Trump was a symptom of a "mean-spirited divide" emerging in the U.S.
"He is a factor in that, but it's not just Trump, it's the followers of Trump who really believe that somehow they have lost... the blacks and browns and Muslims, we've globalized capitol by globalizing human rights," Jackson said.
Jackson concluded, "We've been used as scapegoats for deeper and deeper economic and cultural fears. But we're not the cause of them."
There's no doubt that Jackson was a champion of minorities, social justice, and a catalyst for forwarding civil rights for all Americans.
Setting that aside for a moment, there was a 40 plus year relationship between Trump and Jackson. Did Jackson know - or suspect - that Trump was a racist during those decades? Trump certainly had a record of demeaning minorities, especially blacks. Newspaper accounts listed his racial improprieties throughout those years.
Before Trump got into politics, he donated some of his office space in Manhattan to Jackson's Rainbow/PUSH Coalition.
Fast forward to the 2016 election, Jackson endorsed Democratic opponent Hillary Clinton against Trump. If they weren't already on the outs that cemented the new phase of the Jackson Trump relationship
In 2020, Jackson endorsed Bernie Sanders in the Democratic primary. He was honored as a civil rights icon at the 2024 Democratic National Convention.
So, what can we deduce from that long relationship that eventually went sour?
Maybe Jackson had a Road to Damascus revelation along the way. Whatever happened the two went down vastly different political roads.
As it Stands, like all great men Jackson was a complex man who left behind a civil rights legacy that will continue to go down into history.
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