ii đ˘ LATEST UPDATE: From a writersâ strike podcast to open warfare, Kimmel and Colbertâs alliance becomes Trumpâs biggest late-night threat đĽ
Two late-night titans didnât just crack jokesâthey formed a united front, and Donald Trump saw it as a declaration of war.
Donald Trump has weathered criticism from comedians for years, but something different happened when Jimmy Kimmel and Stephen Colbert began moving in sync. What started as parallel punchlines evolved into a sustained, coordinated spotlight on Trumpâs controversiesâone that blended satire, solidarity, and timing so sharp it left Trump visibly rattled.
The flashpoint came as Congress voted overwhelminglyâ427 to oneâto advance transparency measures tied to long-buried records. Late-night seized the moment. On air, Colbert zeroed in on the lone dissenting vote, using humor to frame a broader narrative about secrecy, power, and accountability. The joke landed because it carried a sting: Americans were watching a rare show of bipartisan agreement collide with an administration accusedârightly or wronglyâof fighting disclosure at every turn.
What truly set Trump off, however, wasnât a single monologue. It was the alliance.
Kimmel and Colbertâs bond hardened during the 2023 Writers Guild strike, when late-night shows went dark and five hostsâKimmel, Colbert, Fallon, Meyers, and Oliverâdid something unprecedented. They launched Strike Force Five, a podcast conceived as both a morale boost and a financial lifeline for out-of-work staff. The show debuted on August 30, 2023, rocketed to the top of podcast charts, and ran for 12 episodes that proved rivals could become brothers-in-arms.
That collaboration mattered more than anyone realized at the time.
By April 2024, Kimmel took center stage at the Oscars and aimed a direct shot at Trump, reading a critical social post live and firing back with a line that sent the room into hysterics. Trump didnât laugh. He stewedâposting repeatedly, attacking Kimmelâs intelligence, and blaming him for ratings dips. The counterpunch came fast. Colbert went on air and drew a bright red line, defending Kimmel not as a colleague but as familyâhis âpodcast brotherââand promising to stand by him.
It wasnât just a joke. It was a signal.
From that moment, Trumpâs frustration appeared to intensify. Late-night monologues increasingly connected dotsâbetween money, influence, media pressure, and political retaliationâusing humor as a delivery system for claims Trump desperately wanted to swat away. Colbert mocked the spectacle of tech executives currying favor. Kimmel leaned into ridicule that felt personal, relentless, and impossible to ignore.
Then came July 2025, the moment supporters and critics alike describe as the real stress test of the alliance. Paramount, CBSâs parent company, agreed to a $16 million settlement with Trump tied to a lawsuit over 60 Minutes editing practices involving a Kamala Harris interview. The settlementâhotly debated and widely criticizedâlanded like a thunderclap across the media landscape. To many observers, it looked less like closure and more like pressure.
Colbert was suddenly in the crosshairs.
Rather than retreat, the partnership hardened. What viewers saw on screenâsharp jokes, mock outrage, cutting sarcasmâmasked a deeper calculation: together, Kimmel and Colbert were harder to isolate, harder to intimidate, and far more dangerous to ignore. Trumpâs public reactions only reinforced that perception, with posts and statements that seemed aimed as much at silencing critics as at winning arguments.
The irony is hard to miss. Trump has long portrayed comedians as irrelevant. Yet when two of the biggest names in late-night synchronized their firepower, his response suggested the oppositeâthat satire, when united and sustained, can cut closer to the bone than any op-ed or press conference.
In the end, this wasnât about a single joke or a single lawsuit. It was about power, pressure, and the unexpected force of solidarity. And for Trump, the real nightmare may not be the secrets themselvesâbut the fact that two voices he canât control decided to tell the story together.
