By High Plains Grifter
Before you spit out your oat-milk latte, hear the Grifter out.
Trump wasn’t cutting big checks to Jesse Jackson’s ’88 presidential run (far as the records show), but he sure as hell gave the man free prime office space at 40 Wall Street for Jackson’s Rainbow/PUSH Coalition Wall Street Project in the late ’90s. That initiative pushed corporations for more minority hiring, board seats, and economic access. In January 1999, Jackson introduced Trump warmly at the event, thanked him for the support, called him a friend who had been “inclusive,” and praised his commitment to underserved communities. In cutthroat Manhattan, that’s not nothing.
He also crossed paths plenty with the Rev. Al Sharpton back in the day. The two New York characters knew each other for decades through Atlantic City boxing deals and local events. Trump cut the ribbon at Sharpton’s National Action Network convention in 2002 and showed up again in 2006, posing with Sharpton, Jesse Jackson, and James Brown. They argued, made deals, asked each other for favors, the classic frenemy dance of big personalities in the city. Different tune once Trump ran as a Republican, of course. Then there’s Whoopi Goldberg on The View. Pre-2015, she openly called Trump a “friend” she liked as a person, even while disagreeing politically. Hugs, laughs, the works. Once he became a GOP threat? Instant personality transplant. Same script as half of Hollywood.
Judge Joe Brown, that no-nonsense former Tennessee jurist, has gone on record multiple times painting a different picture. He talks about Trump hanging out in Harlem circles back in the day, dating a “fine” Black woman (a model type he’d show up with on red carpets right before Melania), and dealing straight with Black entrepreneurs when banks wouldn’t. Brown claims Trump restructured or forgave loans for some brothers in the ’80s/’90s who got squeezed. Anecdotal? Sure. But Judge Brown ain’t exactly a Trump superfan, he’s just calling what he saw.
Trump helped get Nelson Mandela around on his 1990 U.S. tour(after 27 years in prison fighting against Apartheid) by providing a Trump Shuttle 727 (Mandela’s team paid for the charter when others dragged feet—not a freebie, but he didn’t hang up the phone either).
On policy, he signed the FUTURE Act, locking in permanent funding for Historically Black Colleges and Universities (around $255 million a year). Black college leaders took the checks even if they griped about the rest of the agenda. He pushed criminal justice reform via the First Step Act too, real dollars and second chances that hit Black communities hardest.
And the cultural cred? For decades Trump was straight catnip in hip-hop. Rappers stacked his name like a badge of honor: Lil Wayne rapping “Get money like Donald Trump,” Young Jeezy crowning himself “Donald Trump” in the hood, Nelly yelling “Bill Gates, Donald Trump, let me in now.” They weren’t singing about a villain, they were rapping about the ultimate boss move.
Hell, on The Apprentice he fired Black contestants left and right, just like he fired everybody else. That was the game. But he still crowned Randal Pinkett, the first Black winner and a Rhodes Scholar, as his top apprentice and stayed on friendly terms… right up until Trump committed the one unforgivable sin in elite circles: running for president as a Republican and shudders…winning!.
Look, this ain’t a claim that Trump walks on water or that every interaction was perfect. The man has a mouth like a jackhammer and controversies on all sides. But that’s exactly the point. If Bill Clinton’s Southern charm and scandal defense earned him “first Black president” poetry from a literary giant, then Trump’s decades of New York swagger, rap anthems, Harlem nights, HBCU checks, free Wall Street office space for Jackson, Sharpton convention appearances, and crowning a Black Rhodes Scholar on national TV at least qualify him for a tongue-in-cheek bronze medal as #3. So if Trump really is a racist, he has a funny way of showing it.
So go ahead, media, keep clutching your pearls and excluding Donald J Trump from his rightful place as a civil rights trailblazer. But if a saxophone and a scandal made Clinton the First, then the guy who turned “You’re fired!” into a catchphrase while the rappers were chanting his name deserves the third spot.
And I can’t wait to see the Polymarket odds on Barron Trump becoming our Fourth Black President in 2048.
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