Trump pits his military academy photo against teenage Obama after 'obsession' jab

Trump shared a striking side-by-side image that contrasted his polished military school portrait with a college-era photo of Obama puffing a cigarette
Donald Trump was on another social media posting spree on Saturday, June 27, when he shared a striking side-by-side image of himself and Barack Obama in their younger days (AP Photos)
Donald Trump was on another social media posting spree on Saturday, June 27, when he shared a striking side-by-side image of himself and Barack Obama in their younger days (AP Photos)

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'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.

President Donald Trump addresses the crowd as he departs after speaking at the Faith & Freedom Coalition's policy conference at the Washington Hilton, Friday, June 26, 2026, in Washington. (AP Photo/Julia Demaree Nikhinson)
President Donald Trump addresses the crowd as he departs after speaking at the Faith & Freedom Coalition's policy conference at the Washington Hilton on Friday, June 26, 2026, in Washington (AP Photo/Julia Demaree Nikhinson)

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. 

CLARKSTON, GEORGIA - OCTOBER 24: Former U.S. President Barack Obama speaks during a campaign event for Democratic presidential nominee, U.S. Vice President Kamala Harris, at the James R Hallford Stadium on October 24, 2024 in Clarkston, Georgia. Harris and Republican presidential nominee, former U.S. President Donald Trump, continue campaigning in battleground swing states before the November 5th election. (Photo by Alex Wong/Getty Images)
Former President Barack Obama speaks during a campaign event for former Vice President Kamala Harris at the James R Hallford Stadium on October 24, 2024, in Clarkston, Georgia (Alex Wong/Getty Images)

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.



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.



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.”

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