It is a time-honored rule of the modern American presidency that the commander-in-chief should appear above the fray of late-night television. But Donald Trump has never been one for tradition.
In the early morning hours of Friday, May 22, the 79-year-old president proved he was not only awake, but dialed into CBS for the final moments of a late-night institution. Just an hour after the curtain fell on The Late Show with Stephen Colbert, Trump took to Truth Social at 1:52 a.m. ET to deliver a breathless, victory-lap review of his chief comedic rival’s final bow.
“Colbert is finally finished at CBS,” Trump wrote, caps-locking his satisfaction. “Amazing that he lasted so long! No talent, no ratings, no life. He was like a dead person. You could take any person off of the street and they would be better than this total jerk. Thank goodness he’s finally gone!”
The late-night swipe capped off a bitter, year-long saga that bridged the worlds of political vengeance, massive corporate media consolidation, and the shifting boundaries of free speech.
A Star-Studded Farewell and a Corporate Axe
Thursday night’s finale marked the end of an era: a 33-year run for The Late Show franchise on CBS, tracing back to David Letterman’s seismic debut in 1993. Colbert, 62, didn’t go quietly. He packed the Ed Sullivan Theater with a parade of Hollywood heavyweights—including Bryan Cranston, Paul Rudd, Ryan Reynolds, and Jon Batiste—before leading a star-studded, emotional sing-along of The Beatles’ “Hello, Goodbye” alongside Paul McCartney and Elvis Costello.
Yet, the celebratory atmosphere couldn’t entirely obscure the stark political reality behind the show’s sudden demise.
The dominoes began to fall in July 2025. Colbert used his monologue to fiercely criticize CBS’s parent company, Paramount, for agreeing to a $16 million settlement with Trump over a 2024 60 Minutes interview with Vice President Kamala Harris—a lawsuit mainstream First Amendment experts widely dismissed as meritless.
“I believe this kind of complicated financial settlement with a sitting government official has a technical name in legal circles,” Colbert told his audience on July 14, 2025. “It’s a ‘big, fat bribe.’”
Three days later, CBS announced it would not renew Colbert’s contract, citing financial constraints. The timing, however, raised immediate eyebrows across Washington and Wall Street. At that exact moment, Paramount was aggressively pursuing a high-stakes merger with Skydance, led by tech billionaire and Trump ally David Ellison. The deal required the rubber stamp of the Trump administration’s Federal Communications Commission (FCC). On July 25, just over a week after Colbert’s cancellation, the FCC approved the merger.
Trump wasted no time taking credit, even while attempting a tongue-in-cheek denial.
“Everybody is saying that I was solely responsible for the firing of Stephen Colbert from CBS,” Trump posted on July 29, 2025. “That is not true! The reason he was fired was a pure lack of TALENT.”
The Chilling Effect on Late-Night
Colbert was not the only casualty in what critics view as a broader chilling effect on late-night political satire. In September 2025, ABC temporarily pulled Jimmy Kimmel Live! off the air following a controversial monologue targeting the administration.
Now, the corporate and political stakes are rising even higher. Nearly a year after taking the reins at Paramount, Ellison is eyeing an astronomical $111 billion merger with Warner Bros. Discovery—the parent company of CNN. The deal must clear regulators at the FCC and a Department of Justice currently led by Attorney General Todd Blanche, Trump’s former criminal defense lawyer.
The administration has made no secret of its enthusiasm for Ellison’s media empire. Since taking over CBS, Ellison installed Bari Weiss as editor-in-chief of CBS News, shifting the network’s editorial tone toward more favorable coverage of the president and his allies.
The contrast with other networks is sharp. In March 2026, Defense Secretary Pete Hegseth openly lambasted CNN during a Pentagon press briefing, declaring, “The sooner David Ellison takes over that network, the better.”
From Guests to Adversaries
The animosity between Trump and Colbert is a stark departure from how their relationship began a decade ago. Trump appeared on The Late Show just once, in September 2015, as his populist campaign began its historic rise in the Republican primaries. At the time, Trump praised the comedian, telling him, “I watched last night… It was a good show.”
But as late-night comedy transformed into the frontline of the political resistance during Trump’s first term, the relationship soured permanently. By the time Trump returned to the Oval Office, his obsession with his late-night critics had only intensified.
“I don’t watch it—purposely, I don’t watch it,” Trump insisted to Fox News in September 2025, before echoing the exact phrase he would use in his 2 a.m. post on Friday. “I could get people off the street to do a better job than Colbert… I don’t find him good.”
For his part, Colbert appeared at peace with the abrupt ending of his tenure, choosing to view the absurdity of the situation with a trademark dose of perspective.
“The ending of the show aside… we’re clowns,” Colbert said in a recent interview. “How much does it diminish the office of the presidency to even notice what we say?”
As Trump was firing off his early-morning posts from the White House, Colbert was already packing his bags for the president’s home turf. The comedian scheduled a trip to Washington, D.C., on Friday to attend his brother Tommy’s wedding.
“I mean, you can’t do this forever,” Colbert reflected on his exit. “You have to think about, well, when is the right time to end your tenure? I didn’t think this soon, but I mean, who knows? I’m going to get drunk and sing with my family.”