Donald Trump woke up Saturday and chose to embarrass himself. Again. And Barack Obama didn’t even have to show up.
The 80-year-old president had already spent the morning posting AI images of himself as a character from Greek mythology holding the world on his shoulders.
However, he was not done. Something in his mind made him take a shot at Barack Obama.
Trump posted vintage pictures of himself and Obama side-by-side. The idea was to make his predecessor look bad. But similar to his Iran war, it did not go as planned.
On Obama’s side, many saw an 18-year-old at Occidental College, rocking a wide-brimmed hat cocked just right. He also had a cigarette hanging out of his mouth, looking like he invented cool. Obama wasn’t even trying.
That was the problem for Trump.
When people saw the president’s photograph, they saw a stiff kid in a military uniform from his 1964 New York Military Academy yearbook. Interestingly enough, he labeled the shot as “D. Trump, 20.” The problem with the label is that he was 17 when the shot was taken. He got his own age wrong.
Trump’s own niece, Mary Trump, caught it first.
“This is a picture of Donald when he was a teenager in high school,” she wrote on X. “You’d think he’d know that.”
Critics on social media had a field day dragging him.
“Trump just uploaded a side-by-side comparison where Obama looks cool as f—k and he looks like a dork. Nice one Donald,” one person posted. Another added, “Trump just posted a photo of Obama aura mogging him.”
Someone dropped a video next to it — Obama’s Presidential Center opening on one side, Trump’s National State Fair on the other. One looks cool and the other not so much.
lol
— I’m Not That Short (@SheBleedsHipHop) June 28, 2026
“Living rent-free!” somebody wrote, dropping a GIF of Obama posted up comfortably inside Trump’s brain like he owns the place.
hahaha
— I’m Not That Short (@SheBleedsHipHop) June 28, 2026
Then more people started making their own comparisons.
Perfect 👌🏻!!!
— Betsy T (@bubblestrapp) June 27, 2026
One meme put “Obama in 1991 surrounded by law books, first ever Black president of Harvard Law Review” directly next to a photo of Trump with his former associate Jeffrey Epstein.
Obama takes up a lot of space in Trump’s head
— Gigi 😏 (@Gigisaysthis1) June 27, 2026
Another person skipped the subtlety entirely and put Trump’s mugshot beside Obama’s Nobel Peace Prize.
This is the one, above all others that will piss Trump off the most. You guys with large number of followers need to repost this in hopes that somehow Trump gets to see it!! The pic Trump posted almost threw me over the edge. I despise him with every fiber of my being!
— PastyWhiteWoman (@pastywhitewoman) June 27, 2026
“This is the one, above all others, that will piss Trump off the most,” the caption read, “The pic Trump posted almost threw me over the edge. I despise him with every fiber of my being!”
None of this is new.
Trump mentioned Obama’s name in 2019 an average of 1.8 times per day, according to Michigan Chronicle.
Seven years later, he is still tearing Obama down.
Many wonder what the original wound is between the two.
That goes back to April 30, 2011, at The White House Correspondents’ Dinner. Obama stood at that podium and roasted Trump in front of the entire press corps while Trump sat in the audience and took it. That was the night something broke inside him.
Obama takes up a lot of space in Trump’s head
— Gigi 😏 (@Gigisaysthis1) June 27, 2026
I’ve always thought that. Knowing so much more about his fragile ego it all begins to make sense.
— Nancy (@Nancyf4gtr) June 27, 2026
Saturday’s photo post was just the latest proof that it never healed.
Obama finally addressed the whole situation on the “All the Smoke” podcast with Matt Barnes and Stephen Jackson. Barnes asked him about Trump.
“Obviously, you know, I have a room in his head — a suite,” he said. Then he twisted the knife. “When I was president, the last thing I had time to do was worry about what somebody said or what my predecessor did. They’re gone. I’ve got work to do.”
And now Chicago has decided to make it physical.
The month a proposal was introduced to the city council to rename the stretch of North Wabash Avenue where Trump Tower sits to “Barack Hussein Obama Way,” NBC Chicago reported.
A sign would go up directly outside 401 N. Wabash Ave. The proposal dropped the night before the grand opening of the Obama Presidential Center.
But what might be the most nerve-wracking thing is that the results of a new CNN poll show 57 percent of Americans view Obama favorably. Trump sits at 34 percent.
Trump posted an old photo Saturday morning, trying to win. By Saturday night, his own building had a street named after the man living in his head. Obama didn’t campaign for it. He didn’t ask for it. He didn’t even respond. He never has to.
Cool people never let them see them sweat.
