For a presidency that has thrived on spectacle, deflection, and relentless grievance, nothing prepared Donald Trump for the night two late-night juggernauts teamed up and turned him into the biggest national punchline of 2025. It happened during “Brooklyn Week,” a chaotic, weirdly electric media crossover where Jimmy Kimmel appeared on The Late Show and Stephen Colbert walked onto Jimmy Kimmel Live—simultaneously. What unfolded was not comedy. It was a coordinated cultural takedown. A two-network ambush. A tag-team humiliation so precise and so deeply sourced that even loyalists admitted it rattled the former president in ways no prosecutor ever has.
Trump, watching from Florida, cracked first.
THE NIGHT THE WAR BEGAN
The segment that set the entire disaster in motion didn’t even involve Trump at first. Colbert joked about Trump receiving a gold crown in South Korea—a symbolic gesture about the ancient Shilla dynasty. But to Colbert, it was perfect satire fuel: a president who craved royal treatment being presented with a literal crown just weeks after millions of Americans marched chanting, “We don’t want a king.”
Colbert didn’t stop there. He roasted Trump texting Kim Jong-un like a desperate teen—“Should I text him now? No, it’s too soon. Okay I’ll text him again but keep it casual… I love you.” The crowd howled.
But this was only Act I.
THE REAL MOTIVE: TRUMP CAME FOR THEM FIRST
Before the joint attack, both comedians were battling their own political fires.
Colbert’s show was canceled by CBS in July 2025—officially due to finances. Unofficially, everyone inside the building whispered the same truth:
Colbert publicly called Paramount’s $16 million settlement with Trump a “big fat bribe,” and the network panicked.
Kimmel was suspended by ABC in September, after Trump’s FCC chair Brendan Carr threatened the station’s broadcast license. It was the closest America had come to state-ordered censorship of a comedian in modern memory.
So instead of backing down, the two men did what Trump feared most:
They joined forces.
THE OSCARS: KIMMEL’S VIRAL PUNCH
Kimmel struck first.
At the Oscars, standing in front of Hollywood royalty—Robert Downey Jr., Emma Stone, Jodie Foster—he pulled out his phone and read Trump’s rant mocking him:
“Has there ever been a worse host than Jimmy Kimmel at the Oscars?”
Then Kimmel delivered the killshot:
“Thank you, President Trump. I’m surprised you’re still awake. Isn’t it past your jail time?”
The Dolby Theatre exploded.
Jodie Foster doubled over laughing.
Trump’s aides scrambled.
THE OBSESSION: TRUMP CAN’T LET GO
Normal politicians move on.
Trump doesn’t.
For seven straight months, he kept re-posting the same Oscars clip like it was evidence in a conspiracy case.
He attacked Kimmel again in April 2024.
Then October.
Then again in winter.
And always in ALL CAPS.
At one point, he even confused Kimmel with Al Pacino—blasting Kimmel for a mistake Pacino made during an award announcement.
Kimmel’s response:
“Jimmy wasn’t even presenting that award, my dude.”
THE MELANIA TWIST
Then the flashpoint arrived.
Multiple reports surfaced that Melania despised Trump’s plan to demolish the East Wing to build a ballroom. Colbert weaponized the story:
“I too would be concerned if I was expected to slow dance with Donald Trump.”
The audience lost it—and Trump reportedly “erupted in profanity” behind the scenes.
THE IQ MELTDOWN
If there’s one insult Trump always returns to, it’s IQ.
He claimed Jasmine Crockett and Alexandria Ocasio-Cortez were “low IQ,” prompting Colbert to propose the ultimate televised stunt:
The James C. Kimmel Cognitive Aptitude and Mental Brilliance Invitational.
It was genius—because everyone knew Trump would never take a real cognitive test on live TV.
COLBERT’S EXPLOSIVE COUNTERSTRIKE
Then came Trump’s fatal mistake.
He posted another attack:
“Colbert is boring. Not funny. Needs to be fired.”
Colbert walked out the next night, stared directly into the camera, and unleashed the most iconic line of his career:
“Would an untalented man be able to compose the following satirical witticism?
Go f*** yourself.”
The crowd erupted into a standing ovation.
People chanted “STEVEN! STEVEN!”
Trump went nuclear.
THE CANCELLATION — AND TRUMP’S CELEBRATION
CBS then announced Colbert’s contract would not be renewed.
Trump celebrated:
“I LOVE that Colbert got fired. Kimmel is next!”
Colbert laughed:
“Kimmel, I am the martyr. There is only room for one on this cross.”
KIMMEL SUSPENDED — AND COLBERT GOES FULL DEFCON 1
When Kimmel was suspended after Trump’s FCC threats, Colbert dedicated his entire show to defending him:
“Tonight, we are ALL Jimmy Kimmel.”
He accused Trump of behaving like an autocrat.
David Letterman emerged from retirement, calling Trump an “authoritarian criminal.”
It was a cultural earthquake.
THE ULTIMATE HUMILIATION: SEPTEMBER 30, 2025
Then came the night Trump could not survive.
Kimmel appeared on Colbert’s show.
Colbert appeared on Kimmel’s.
The same jokes.
The same receipts.
The same timeline of corruption, incompetence, ego, and obsession.
It was the first-ever dual-network coordinated political roast in television history.
They mocked:
• Trump’s rage over soybeans
• His meltdown over China tariffs
• His love letters to Kim Jong-un
• His spelling disasters (“covfefe,” “Nambia,” “muterers”)
• His self-comparisons to dictators
• His paranoia toward comedians
• His gold obsession
• His threats toward networks
• His obsession with ratings
• His weird fixation on Kimmel’s Oscars monologue
• His inappropriate comments toward young audiences
• His self-appointed “king” image
• His endless grudges towards female critics
It was fact-checked comedy. Weaponized satire. A cultural court hearing with jokes sharper than subpoenas.
TRUMP’S 3 A.M. MELTDOWN
At 3:08 a.m., Trump unleashed 12 posts on Truth Social in 90 minutes.
All caps.
Misspellings.
Personal attacks.
Threats against networks.
Rants against “failing comedians.”
Weird insults about soybeans.
A paragraph about Melania’s jacket.
Accusations that AOC “couldn’t pass a test.”
Claims he would “CRUSH Colbert in an IQ duel.”
The meltdown was so extreme that even conservative commentators called it “unhinged.”
And the comedians?
They didn’t say a word.
They didn’t need to.
The world had already seen the damage.
