Trump pits his military academy photo against teenage Obama after 'obsession' jab
WASHINGTON, DC: Donald Trump dusted off an old photo to deliver a fresh jab at Barack Obama, days after the former president accused him of being "obsessed" with him.
The 80-year-old president was on another social media posting spree on Saturday, June 27, when he shared a striking side-by-side image that contrasted his polished military school portrait with a college-era photo of Obama puffing a cigarette.
Trump just posted a photo of Obama aura mogging him pic.twitter.com/TEU9QliLhR
— Adam Mockler (@adammocklerr) June 27, 2026
Trump's post comparing his youthful self and Obama
Trump’s taunting post featured a photograph of him in a military uniform from his time at the New York Military Academy.
In 1959, when he was 13, his father, Fred Trump, sent him to the private military-style boarding school in Cornwall-on-Hudson. He remained at the academy for the next five years, graduating in 1964.
Right next to Trump’s pinned-up image was a photo of a college-aged Obama, wearing a Panama hat, and smoking what appears to be a cigarette, a habit the former president has admitted he's struggled with since his teen years.
Photographer Lisa Jack took the photo during his time at Occidental College.
While Trump captioned the photos, “D. Trump, 20” and “B.H. Obama, 18,” his niece and frequent critic, Mary Trump, was among those who pointed out that Trump attended the military academy as a teenager, graduating in 1964 at 17.
Trump’s posting spree didn’t just include a taunting dig at Obama but also a post comparing him to the Greek mythological character Atlas.
Trump posts himself as ATLAS holding up Earth with American flag pic.twitter.com/Y8sEkqQaB2
— RT (@RT_com) June 27, 2026
On Saturday, the Republican leader posted what appears to be an AI-generated image depicting himself literally holding the world on his shoulders. He is on one knee and is draped in an American flag.
The image appears to reference Atlas, the Titan from Greek mythology, condemned to carry the celestial heavens on his shoulders.
Obama thinks he 'has a suit' in Trump's head
Trump’s taunting comparison post came after Obama said he thinks the 80-year-old has an “obsession” with him, existing in a “suite in his head.”
'All the Smoke' podcast co-host and former NBA player Matt Barnes spoke with Obama about Trump being “very fascinated with you and your family,” but did not name the 47th president.
🚨WATCH: Barack Obama on Donald Trump:
— THE GLOBAL WATCHDOG (@glwatchdog) June 27, 2026
I obviously, you know, have a room in his head. Rent-free.
Look, first of all, 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.… pic.twitter.com/c8or4FqusJ
He praised Obama for meeting Trump’s “negativity and racism with class” before he asked if Obama ever wants to “cuss his a– out sometimes?”
“The thing about it is, look, you’ve got to ask him what it is,” Obama said before Barnes added, “The obsession.”
“The obsession,” Obama repeated. “I obviously have a room in his head, a suite in his head.”