Letterman Slams Trump: 'Expect Ridicule,' Crowns Kimmel 'Resistance' Leader
David Letterman, 2019. Photo courtesy of Zach Catanzareti under CC BY 2.0.
David Letterman just dropped a truth bomb on late-night TV's front lines. Sitting down with Jimmy Kimmel, the former "Late Show" host didn't hold back about President Donald Trump's place in the spotlight. "If the leader of the free world is a fool," Letterman said, "the leader of the free world, then, should expect and examine every bit of ridicule he receives," as reported by The Daily Beast.
The jab wasn't just a throwaway line. It came wrapped in praise for the resilience of late-night hosts who keep pushing back against the administration's attempts to silence them. Letterman reportedly singled out Kimmel, Stephen Colbert, and Seth Meyers for their "masterful job of defending democracy" through satire, even as the pressure to shut them down mounts, according to Entertainment Weekly.
The 'Resistance's Unlikely Champion'
Letterman's comments came during a rare appearance on "Jimmy Kimmel Live!" where he crowned Kimmel "the leader of the resistance" against Trump's presidency, as reported by Fox news. The title was met with Kimmel's self-deprecating humor, calling himself "the totally ineffective leader of the resistance."
The irony is thick. Letterman, who retired from late-night years ago, feels safer calling out the president than the hosts currently on air. Kimmel's show was pulled temporarily after his controversial comments about the assassination of conservative activist Charlie Kirk, a move widely seen as a response to political pressure.
The suspected murderer of Charlie Kirk is Tyler Robinson. Kimmel's comments reportedly suggested the assassin was a Trump supporter, which sparked backlash and led to his suspension.
Despite the suspension, ABC renewed Kimmel's contract through 2027, signaling a commitment to keeping his voice on the airwaves even as Trump publicly demanded his firing. Trump's social media attacks have targeted Kimmel repeatedly, calling him "a man with NO TALENT and VERY POOR TELEVISION RATINGS" and demanding he be removed from the air, as reported by Entertainment Weekly.
Late-Night's Frontline Battle
Letterman didn't just praise Kimmel. He also applauded Colbert and Meyers, who have faced their own share of Trump's ire. The president has called for Meyers to be "fired immediately" after critical commentary, with FCC Chair Brendan Carr amplifying those calls on social media, as reported by The Daily Beast.
Yet, all three hosts have reportedly secured contract extensions that will keep them on air for the foreseeable future. Fallon and Meyers renewed their deals with NBC through 2028, while Kimmel's recent one-year extension with ABC runs through May 2027,
Letterman expressed relief at not having to navigate this minefield himself. "I'm so glad to be out from under this mess," he said, as reported by The Daily Beast, acknowledging the high stakes for those still in the trenches.
When Comedy Meets Politics
The tension between late-night hosts and the Trump administration has been a defining feature of the current political climate. Letterman's remarks highlight the role satire plays in holding power accountable, even as the administration pushes back hard.
The attempts to silence dissent have reportedly included threats to pull shows, public calls for firings, and pressure on networks. Paramount's decision to end "The Late Show" with Colbert in 2026 came shortly after Colbert criticized the company for settling a lawsuit with Trump. Some saw this as capitulating to political pressure.
Kimmel's suspension after his Charlie Kirk comments was another flashpoint. The network's swift action followed public outcry and pressure from Trump's FCC chair. But Kimmel's return to air and contract extension suggest a pushback against censorship.
The Price of Speaking Out
Letterman's words underscore a stark reality: speaking truth to power in today's political climate carries real risks. The veteran comedian's relief at being retired contrasts sharply with the precarious positions of current hosts who face threats to their careers for doing what late-night has traditionally done — poke fun at those in power.
"You see how that makes me look good," Letterman joked, as reported by Fox News, acknowledging the irony of his safer perch while praising Kimmel's courage.
For viewers, this ongoing battle plays out nightly on screens across the country. The resilience of these comedians, despite the administration's efforts to silence them, reflects a broader struggle over free expression and the role of media in democracy.
What's Next for Late Night?
With contracts secured and audiences engaged, Kimmel, Colbert, and Meyers seem poised to continue their critical commentary. Letterman's endorsement adds weight to their efforts, framing their work as essential to defending democratic values.
As Letterman put it, "Thank God for you, thank God for others, SNL and everybody else... I think it's the way things need to be in a democracy that's seemingly this crippled," as reported by Entertainment Weekly.
The stakes remain high. The administration's repeated calls to silence dissenting voices have not succeeded — yet the tension between political power and free speech continues to simmer, with late-night comedy at the heart of the fight.
You can bet the spotlight will stay on this battle, with Letterman's words echoing as a reminder: if you're the leader of the free world and you act foolishly, ridicule is not just inevitable — it's part of the job.
References: Letterman Hammers 'Fool' Trump: He Should 'Expect Ridicule' | David Letterman praises Jimmy Kimmel as the 'leader of the resistance' | Letterman calls Kimmel 'leader of the resistance' against Trump
