Countdown with Keith Olbermann

Episode: "TRUMP DECLARES CRITICISM OF HIMSELF 'REALLY ILLEGAL' - BULLETIN 9.19.25"
Date: September 19, 2025
Host: Keith Olbermann

Episode Overview

In this urgent bulletin episode, Keith Olbermann reacts to President Donald Trump's unprecedented declaration during a White House news conference that criticism of himself is "really illegal." Olbermann frames this as a critical moment for American democracy, highlighting the broader climate of political intimidation, threats against media freedom, and the chilling effect of governmental overreach—particularly in the aftermath of FCC Commissioner Brendan Carr's pressure campaign on ABC and Disney, which led to Jimmy Kimmel's suspension. The episode weaves together these alarming developments, critiques the silence or acquiescence of major media leaders, and draws from historical precedent to underscore the dangerous path on which the Trump administration is heading.

Key Discussion Points & Insights

1. Trump Declares Criticism of Himself "Really Illegal"

[02:20–04:33]

• President Trump, during a news conference, stated:
  • "See, I think that's really illegal personally." ([Donald Trump, 04:25])
• The conference was initially meant to discuss business visa waivers but veered dramatically when Trump labeled negative media coverage and criticism as illegal.
• Olbermann stresses the gravity:

  "Donald John Trump cannot remain president after that. He cannot, you cannot declare that criticism of a president, any president, is illegal." ([Keith Olbermann, 04:33])

• Olbermann contextualizes Trump’s remark as unprecedented, even by Civil War or wartime standards.

2. Free Speech, "Cancel Culture," and Media Intimidation

[03:14–04:33], [08:01–13:25]

• Trump's comments were prompted by a question on free speech and the distinctions between cancel culture and consequence culture.
• Olbermann discusses the chilling effect of Trump's attitude, especially as it coincides with recent government threats against the media.
• The FCC, under Brendan Carr, reportedly threatened ABC and Disney to pressure them into removing Jimmy Kimmel’s show after his remarks about Charlie Kirk’s death:

  "What Carr said this week, we can do this the easy way or the hard way. These companies can find ways to take action on Kimmel or there is going to be additional work for the FCC ahead." ([Keith Olbermann, 06:21])

• Olbermann accuses the administration of blackmail-like intimidation and calls attention to serious threats against independent journalism.

3. The Jimmy Kimmel and Charlie Kirk Controversy

[06:21–08:03]

• Kimmel offered condolences for Charlie Kirk yet was removed from the air, allegedly under FCC pressure.
• Olbermann argues that Kimmel’s remarks were factual, not defamatory:

  "100% across the board, Kimmel's remarks about the late Charlie Kirk have been mischaracterized... Jimmy Kimmel started his segment about Charlie Kirk by expressing sorrow and his remorse…" ([Keith Olbermann, 07:41])

• Olbermann criticizes the reaction from media organizations, particularly ABC/Disney's lack of resistance.

4. Unlikely Criticism from Ted Cruz

[08:21–10:34]

• Senator Ted Cruz, often aligned with right-wing positions, surprisingly denounces the FCC and the administration's actions:

  "I gotta say, that’s right out of Goodfellas. That’s right out of a Mafioso coming into a bar going, 'Nice bar you have here. It’d be a shame if something happened to it.' ... I think it is unbelievably dangerous for government to put itself in the position of saying, 'We’re going to decide what speech we like and what we don’t.'" ([Ted Cruz, 09:39])

• Cruz warns such tactics could later justify silencing conservatives.
• Olbermann admits Cruz is "90% correct," only differing on references and the accuracy of calling Kimmel a liar ([Keith Olbermann, 10:42]).

5. Other Voices and the Media’s Response

[11:47–12:56]

• Michael Eisner, former Disney Chairman, publicly condemns ABC/Disney’s capitulation:

  “…the suspending indefinitely of Jimmy Kimmel immediately after the chairman of the FCC’s aggressive yet hollow threatening of the Disney company is yet another example of out of control intimidation.” ([Michael Eisner, 12:31]) “Maybe the Constitution should have said…’Congress shall make no law abridging the freedom of speech or of the press except in one’s political or financial self-interest.’” ([Eisner, 13:03])

• Olbermann notes many current media leaders and public figures remain silent, fueling the chilling effect on public discourse.

6. Historical Perspective: Theodore Roosevelt and the Value of Criticism

[13:17–13:55]

• Olbermann recalls a 1918 speech by Theodore Roosevelt, underscoring the deep American tradition of critical dissent:

  “To announce that there must be no criticism of the President... is not only unpatriotic and servile, but is morally treasonable to the American public.” ([T. Roosevelt, quoted by Olbermann, 13:27])

7. Final Warning: The Slippery Slope

[13:55–15:59]

• Olbermann warns that, if allowed to stand, Trump’s logic could lead to broad labeling of dissenters as “terrorists” (e.g., by designating critics as "Antifa").
• Urges media leaders and the public to defend free speech actively and not cower before political intimidation.

Notable Quotes & Memorable Moments

• Trump's Outrageous Claim:

  "See, I think that's really illegal personally." ([Donald Trump, 04:25])

• Olbermann's Response:

  "Donald John Trump cannot remain president after that." ([Keith Olbermann, 04:33])

• On FCC Blackmail Tactics:

  "We can do this the easy way or the hard way." ([Brendan Carr, paraphrased by Olbermann, 06:21])

• Ted Cruz on Abuse of Power:

  "That's right out of Goodfellas... It is unbelievably dangerous for government to put itself in the position of saying, 'We're gonna decide what speech we like and what we don't.'... We should not be in this business." ([Sen. Ted Cruz, 09:39, 10:09])

• Michael Eisner's Lament:

  "The suspending… of Jimmy Kimmel… immediately after the chairman of the FCC’s aggressive yet hollow threatening… is yet another example of out of control intimidation." ([Michael Eisner quoted by Olbermann, 12:31])

• Theodore Roosevelt’s Principle:

  "To announce that there must be no criticism of the President... is… morally treasonable to the American public." ([T. Roosevelt, quoted, 13:27])

Important Segment Timestamps

• 02:20–04:33: Trump declares criticism of himself illegal; Olbermann highlights unprecedented nature.
• 06:21–08:01: Deep dive into FCC threats; ABC/Disney suspend Kimmel; issue of media capitulation.
• 08:21–10:34: Ted Cruz voices rare, forceful opposition to government censorship/intimidation.
• 11:47–13:03: Michael Eisner’s public censure of Disney’s surrender and defense of free speech.
• 13:17–13:55: Historical perspective from Theodore Roosevelt on the patriotism of dissent.
• 13:55–15:59: Olbermann’s warning of further abuses and urgent call to action.

Tone

Olbermann’s delivery is urgent, pointed, and impassioned—a blend of outrage, historical gravitas, and journalistic clarity. He uses biting sarcasm (“I will have to go and lie down after saying that… Ted Cruz is as right as he ever has been”) and moral seriousness, underscoring the dangerous implications of the week’s events for American democracy.

Summary

This episode is a forceful, urgent warning about the erosion of free speech and the alarming rise of government intimidation against critics and journalists. Using Trump's extraordinary claim as the fulcrum, Olbermann explores a web of official threats, media compliance, rare dissent from within the president's party, and historical reminders of the value of criticism. He calls on leaders and the public to defend the First Amendment, making clear that criticism of power is not only a right—but a patriotic duty.