John Oliver Exposes Trump’s ‘Epic Run’ of ‘Losing Fights’

DONE WINNING

The late-night host explained why the president is losing his “air of invincibility.”

John Oliver
HBO

John Oliver exposed Donald Trump’s uncanny ability to pick “losing fights.”

The late-night host returned with a new episode of HBO’s Last Week Tonight, where he had plenty to unpack, from the 79-year-old president’s AI-generated image of himself depicted as Jesus to his ongoing war of words with the pope.

Oliver, 48, noted Trump’s viral Truth Social post in which he ranted about Pope Leo XIV. Amongst his many complaints, Trump claimed that the Chicago-born pontiff is “weak on crime.”

“In terms of insults,” Oliver said, Trump’s remark “just doesn’t work.”

Donald Trump
"Whatever air of invincibility he had last year is fading fast," theorized John Oliver about the president. Nathan Howard/Reuters

“It’s like saying this possum is weak on Balkan geography: OK, but who gives a s--t? It’s not a possum’s job to correctly place Bosnia and Herzegovina on a map. Her job is to eat garbage, hang upside down, and, by this evidence, f--k,” he quipped, displaying photographs of a possum surrounded by offspring.

Oliver turned to display the now-infamous image of Trump surrounded by disciplines and holding a celestial orb of light in his palm. After intense backlash, the president deleted the image and insisted that the photograph was meant to depict him as a doctor. That excuse, said Oliver, was “pretty weak.”

“Oh, that makes sense, a doctor!” he said. “You know how when you go to the doctor, and you get checked in by a nurse and a few bald eagles, and then the doctor comes in and he’s wearing an ancient tunic and says, ‘We’re gonna get you started on antibiotics and on orbs of light born from my very skin. Take them with food.’”

The president's account deleted the image of him like Jesus from Truth Social on Monday. Donald J. Trump/Truth Social.
The president’s account deleted the image of him like Jesus from Truth Social last week. Donald J. Trump/Truth Social

Oliver then mocked the president for his feud with the pope, saying that this “battle of words has not gone well for Trump.”

“Plus, I don’t think they’d see eye to eye on much other than maybe whether it’s a good idea to cover your workplace in more gold s--t than seems physically possible,” he quipped.

Pope Leo XIV presides over a Prayer Vigil and Rosary for Peace, in Saint Peter's Basilica at the Vatican, April 11, 2026.
John Oliver posited that Trump is losing the “battle of words” with Pope Leo XIV. Remo Casilli/Reuters

According to Oliver, this series of blunders is yet another reminder of the president losing his ability to win a fight.

“The point is, Trump seems to be on an epic run of picking losing fights, and whatever air of invincibility he had last year is fading fast,” Oliver said. “All of which is a pretty good reminder that one day he is gonna be gone.”

Obsessed with pop culture and entertainment? Follow us on Substack and YouTube for even more coverage.