President Donald Trump appeared to be trying to score a quick online win over Barack Obama. Instead, the internet handed him another humiliation.

The 80-year-old president spent Saturday posting a stream of AI-generated images and throwback content on Truth Social, including one bizarre image showing himself as God holding the world on his shoulders. But it was a different post that set off the biggest wave of mockery.

Trump shared a side-by-side image comparing himself as a young man to former President Barack Obama as a teenager. The apparent goal seemed obvious: make Trump look disciplined and presidential while casting Obama as less serious.

But the internet saw something very different.

In the photo, Trump is shown in uniform at the New York Military Academy. He labeled the image as himself at age 20, though the picture is actually from his 1964 high school yearbook, when he was 17.

Next to it was a photo of Obama at age 18, cigarette in mouth, during his freshman year at Occidental College in Los Angeles.

The comparison immediately backfired.

“We all know who the better hang is,” one social media user joked.

Another said Obama was “aura mogging” Trump, using internet slang for someone who looks effortlessly more confident, cool and dominant.

Others quickly pointed out the irony of Trump using a military school photo, despite never serving in the military. Trump received five draft deferments during the Vietnam War era, including four for education and one medical deferment.

“His parents sent him to a military boarding school for behavioral issues & bullying,” one user wrote on X. “Now he uses the photo to pretend he was in the military.”

Trump attended New York Military Academy, a boarding school about an hour north of New York City. His father, Fred Trump, reportedly sent him there after concerns about his behavior as a teenager.

One former roommate at the academy, Art Davie, previously told The Daily Beast that Trump already had an outsized opinion of himself as a teen.

“He was an egomaniac when he was 16,” Davie said. “He was a great flag waver for himself. He wanted everyone to recognize he was the GOAT in everything he did out there.”

Obama’s photo, meanwhile, came from his college years, when he posed for candid black-and-white portraits taken by a fellow student in her Los Angeles apartment. The cigarette in the image reflects a habit Obama has publicly discussed trying to quit.

But if Trump expected the old photo to make Obama look bad, critics say he badly miscalculated.

The backlash only grew after another user posted a different comparison: Obama at age 46 during his 2008 presidential campaign beside Trump at 46 with Jeffrey Epstein, the convicted sex offender who was once part of Trump’s social circle.

That version of the comparison was far less flattering for Trump.

“Obama Derangement Syndrome,” one person wrote, flipping Trump’s own favorite insult, “Trump Derangement Syndrome,” back at him.

“He talks about ‘TDS’ but he has ‘ODS,’” another user added, claiming Obama “lives rent-free” in Trump’s head.

The White House did not immediately respond to a request for comment.

Trump’s fixation on Obama has been a recurring theme for years. According to CNN, Trump has mentioned Obama’s name an average of 1.8 times per day since the former president left office.

But the attacks do not appear to have damaged Obama’s standing with the public. A CNN/SSRS survey conducted in June found that 57 percent of Americans had a favorable view of Obama, compared with 34 percent for Trump.

Obama himself addressed Trump’s repeated references to him during a recent appearance on the All The Smoke podcast, calling the behavior “very strange.”

“Obviously, you know, I have a room in his head—a suite in his head,” Obama said.

For Trump, the throwback post may have been meant as a dig at his longtime political rival.

Instead, critics say it turned into yet another reminder that Obama may still be living in his head rent-free.


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