Donald Trump shared comparison photos of himself and Obama in their teens, in what people are calling the funniest self-own since records began
If you ever feel the stirrings of imposter syndrome, just take a glance in the direction of six-times-bankrupted draft-dodger, Donald Trump, who has twice won the US presidential election based on his reputation as a great businessman, and patriot.
As his personal and professional failures mount up, he turned to the man who lives rent-free in his largely empty head to give his ego a totally unnecessary boost.

Whoever thought it was a good idea to add the spliff –
a. is racist
b. is terrible at photo-editing.
c. has grossly misunderstood how much the young Obama leaves the young Trump in his wake – with or without the edit.
What’s more – he wasn’t 20…
This is a picture of Donald when he was a teenager in high school. You'd think he'd know that. 😂 pic.twitter.com/1BkCjpFPFu
— Mary L Trump (@MaryLTrump) June 27, 2026
You can judge whether he’s lying by two tells – his lips are moving, or he’s writing it down.
People couldn’t quite believe the level of self-own Trump had achieved without even trying.
1.
We all know who the better hang is pic.twitter.com/BtOCSJ4ItQ
— Aaron Rupar (@atrupar) June 27, 2026
2.
It’s the first cope presidency pic.twitter.com/C884jCcKIy
— evan loves worf (@esjesjesj) June 27, 2026
3.
He lies so much he even lies about his age in this photo to make it seem he was wearing a military uniform when he was 20. pic.twitter.com/GcBXzcmOSS
— Ben Meiselas (@meiselasb) June 27, 2026
4.
Trump just uploaded a side by side comparison where Obama looks cool as fuck and he looks like a dork. Nice one Donald pic.twitter.com/wIEyzEVVVy
— Harry Sisson (@harryjsisson) June 27, 2026
5.
Guess which one ended up becoming a convicted felon. pic.twitter.com/8o39Pr5bjs
— Alex Cole (@acnewsitics) June 27, 2026
6.
Obama occupies the penthouse in Trump's demented mind pic.twitter.com/jTImDfBJaz
— Molly Ploofkins (@Mollyploofkins) June 27, 2026
7.
Joe Biden at 20 > Donald Trump at 20 https://t.co/7oqeO3J7gi pic.twitter.com/iBE8fNaEKA
— Chris D. Jackson (@ChrisDJackson) June 27, 2026
8.
FACTS: Obama did not just break Trump. Obama BULLDOZED Trump. His weird obsession with Obama is unexplained. He HATES the fact that this smart black man was a president and WAY MORE popular than him. Obama was COOL in high-school. Trump was a chubby DUMB DORK. https://t.co/f2i15JrMgU
— Dark Brandon (The 46) 🇺🇲 (@ajalexander944) June 27, 2026
9.
Obama Derangement Syndrome pic.twitter.com/3uXVLQPhol
— Republicans against Trump (@RpsAgainstTrump) June 27, 2026
10.
— MeidasTouch (@MeidasTouch) June 27, 2026
11.
Trump just posted a photo of Obama aura mogging him pic.twitter.com/TEU9QliLhR
— Adam Mockler (@adammocklerr) June 27, 2026