Over the weekend, President Donald Trump’s attempt to drag former President Barack Obama with a throwback photo post quickly turned sour. Users quickly pointed out the comparison actually worked more in Obama’s favor than in his.  

On Truth Social, Trump shared two images: a side-by-side photo of himself in a military academy uniform and Obama as a college student, smoking a cigarette. Apparently, it was a jab meant to highlight the sharp contrast between the two men and their younger selves.

Instead, the post sparked jokes, criticism, and reignited commentary about Trump’s fixation on his predecessor.

“Curious what the messaging goal is here,” former Obama aide and “Pod Save America” co-host Tommy Vietor wrote. “One guy looks like a good hang while other looks like he would’ve been fragged by his unit in Vietnam (if he hadn’t gotten five deferments).”

Some online users mocked the move as “Obama Derangement Syndrome,” a twist on Trump’s own “Trump Derangement Syndrome” line for critics. Others focused on the image details, noting that Trump’s photo was from his yearbook at the New York Military Academy and showed him as a teenager, not 20, as the post suggested.

The timing of the post also felt messy: only days earlier, Obama shrugged off Trump’s repeated attacks in an appearance on the “All the Smoke “podcast, calling his obsession with him “strange” and saying it says more about Trump’s priorities than his own. 

“The idea that I’d be worrying about somebody who came before and me trying to measure like, ‘What’s he done today?’ Look, constantly worrying about that is a strange thing to me,” Obama said. “It shows me somebody who is not focused on the American people and the job they’re supposed to do.”

Obama also joked that he has “a suite” in Trump’s head, referring to frequent comments online that he lives “rent-free” in Trump’s head.

For many users, the side-by-side did the opposite of what Trump likely intended: it made Obama look cool, confident, and fully unbothered.