Trumpland

Why Trump’s Obsession with Obama is Even More Twisted than You Think

JEALOUS, MUCH?

Donald Trump’s obsession with Barack Obama isn’t about politics, writes Don Lemon. It’s about race, resentment and the lie that white mediocrity deserves power.

Opinion
Donald Trump, Barack Obama
Photo Illustration by Eric Faison/The Daily Beast/Getty Images

Don Lemon is the host of The Don Lemon Show on YouTube.

Rome didn’t fall in a day. It collapsed over time, hollowed out by greed, distraction, corruption and ego. If America falls, it won’t be from war, disease or even an insurrection. It will be because one man couldn’t take a joke.

I remember the 2011 White House Correspondents’ Dinner vividly. I didn’t attend that year; I anchored live coverage for CNN. That night, President Barack Obama stood before a ballroom full of journalists and lawmakers and delivered—as was tradition—a few barbs.

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One was aimed squarely at Donald J. Trump.

Trump had, at that time, spent years promoting a racist lie that Obama wasn’t born in the United States. In his speech, Obama exposed the divisive absurdity with his trademark calm and wit.

“No one is prouder to put this birth certificate matter to rest than ‘The Donald,’” Obama said. “And that’s because he can finally get back to focusing on the issues that matter: Like, did we fake the moon landing? What really happened in Roswell? And where are Biggie and Tupac?”

“All kidding aside,” he continued, addressing Trump directly, “We all know about your credentials and breadth of experience. For example, just recently, in an episode of (The) Celebrity Apprentice, at the steakhouse, the men’s cooking team did not impress the judges from Omaha Steaks. There was a lot of blame to go around, but you recognized that the real problem was a lack of leadership. So ultimately, you didn’t blame Lil Jon or Meat Loaf. You fired Gary Busey. And these are the kinds of decisions that would keep me up at night.”

Donald Trump and Melania Trump pose on the red carpet as guests make their way to the White House Correspondents Dinner at the Washington Hilton Hotel on April 30, 2011, in Washington, D.C.
Donald Trump and Melania Trump pose on the red carpet ahead of the 2011 White House Correspondents Dinner. Something shifted in that moment as Obama's jokes rang true. Trump had been ridiculed before, but never like that, writes Don Lemon. Never so effortlessly. Never so deservedly. That night wasn’t a punchline. It was a prelude. The Washington Post/The Washington Post via Getty Im

The laughter came fast and full. Not cruel, but cleansing. The way truth feels when it’s finally said aloud. The room saw it. Obama saw it. And Trump felt it.

He didn’t laugh. He didn’t blink. He sat frozen, jaw clenched. Seething.

Something had shifted. Not in the room. In him. The moment didn’t just bruise his ego. It cracked something open.

It wasn’t the joke that broke him. It was the realization that the world was laughing. Not with him, but at him. And that the man commanding that laughter was Black.

What we’re witnessing now, this slow collapse of democratic norms and personal vendetta masquerading as leadership, began that night, with a joke and a grudge.

This week, Trump told reporters his Department of Justice should investigate Obama for treason, echoing baseless claims pushed by former Democrat turned MAGA loyalist Tulsi Gabbard. It wasn’t a slip or a misstatement. It was a warning. A fantasy made public. Over the past week, he has similarly shared AI video of Obama being arrested, as well as a viral meme placing himself and Obama in a photo of the 1994 police chase of O.J. Simpson.

Trump doesn’t want justice. He wants revenge. He wants to erase the man who reminds him of everything he can never be. Because the truth, the one that eats away at him, is that Trump is envious of Barack Obama. He always has been.

Trump said that the Department of Justice should investigate Obama for treason.
Trump has said that the Department of Justice should investigate former President Obama for treason. Andrew Harnik/Getty Images

Trump envies Obama’s education. He envies Obama’s elegance. He envies Obama’s marriage. (Barack and Michelle are a partnership. Trump and Melania often look like a ceasefire.) And he envies that Obama is loved. Deeply. By millions around the world who still see in him something aspirational. By history.

Trump wants that. But he’ll never earn it. So he’s spent more than a decade trying to destroy it. And what’s worse is that he started to believe his own myth. He read too much of his own press. He convinced himself that the character he played on TV—the tough boss, the dealmaker, the billionaire—was real. He mistook ratings for respect. The media helped. They fed the illusion because it sold ads and clicks. They gassed him up and made him look competent.

Of course, his followers fell for it. They had to. Because he became their idea of what a successful white man should be: loud, shameless and undeservedly rich. He makes the mediocre feel superior by reminding them that excellence can still be ignored.

Trump has been attacking Obama on social media after Tulsi Gabbard accused the former president of committing “treasonous conspiracy.”
Trump has been attacking Obama on social media after his Director of National Intelligence Tulsi Gabbard accused the former president of committing “treasonous conspiracy.” Meg Oliphant/Getty Images

It’s the same cultural trick we’ve seen for generations. The formula hasn’t changed. It’s how white artists mimicked Black brilliance, profited off it and were labeled icons while the originators were left behind.

To Black America, and to anyone paying attention, it’s stunning—but not surprising. Trump is the political cover band. The tribute act. A hollow imitation of leadership dressed up in flags and grievance.

This isn’t political theater. It’s racial psychodrama. And I say this as a Black man in America who’s not only seen this story before, but has lived it. Baldwin wrote about it. Douglass survived it. Malcolm called it what it was. And Obama, for eight years, stood in its center without flinching.

America has always punished Black men who lead with confidence, who command respect without begging for it, who step into rooms and don’t shrink. That’s what Trump saw that night. A man he couldn’t intimidate. A man who didn’t have to lie to be loved. A man who made him feel small.

Still, Director of National Intelligence Tulsi Gabbard has claimed Obama officials needed to be investigated and charged—including Obama himself.
Tulsi Gabbard has accused Obama and his top national security officials of manipulating intelligence in order to link Trump to Russian election interference. Chip Somodevilla/Getty

And now he has become the Trojan horse for a movement built on the illusion of white competence. He’s cleared the way for others like Gabbard, Sean Duffy, Pete Hegseth, Pam Bondi and Kristi Noem to ascend on “vibes,” not merit. They are, by their own standards, the DEI hires. They rage against diversity, equity and inclusion, but what they really mean is that they’re mad the playing field is no longer tilted entirely in their favor. It’s about maintaining the illusion that they are owed power, no matter what.

The illusion of white merit has always been protected by something much older and uglier—white supremacy. Trump is just its most cartoonish vessel.

Trump demanded Obama’s birth certificate because he assumed it could erase his legitimacy—and confer it. But no paper, no title, no presidency will ever give him what Barack Obama earned with brilliance, composure and a Blackness he will never stop fearing.

Trump's loyal supporters have gradually been losing faith in the president.
Are some Trump's loyal supporters gradually been losing faith in their president? Jeff Kowalsky/AFP via Getty Images

That’s what “Make America Great Again” really means. A longing for the days when men like Trump didn’t have to compete with men like Obama. When power was inherited, not earned.

Trump wasn’t robbed of greatness. He was never great to begin with. And that lie is collapsing. The fear is showing. The rage is louder. The mask is off.

Because here’s the truth America still struggles to face: Black brilliance doesn’t need permission to exist. And white mediocrity can no longer count on immunity.

With research contributed by Peter Rothpletz.

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