Countdown with Keith Olbermann

Episode: DE-FUND THE TRUMP DICTATORSHIP
Date: October 27, 2025
Host: Keith Olbermann (iHeartPodcasts)
Summary by Podcast Summarizer

Episode Overview

This episode of Countdown with Keith Olbermann takes direct, urgent aim at the authoritarianism of Donald Trump’s current presidency, detailing a litany of alleged illegal and dictatorial acts by Trump and his administration. Keith argues for a bold, state-led financial resistance—urging blue states to withhold federal tax payments until Trump resigns. The show features his trademark biting analysis, the “Worst Persons in the World” segment lampooning public figures, and an extended “Things I Promise Not to Tell,” this time recounting his firsthand involvement in the infamous 2000 World Series Clemens-Piazza bat incident. As usual, Olbermann’s style is passionate, acerbic, and packed with political, media, and sports anecdotes.

Key Discussion Points & Insights

1. Special Comment: Trump as a Lawless Dictator

[01:47–15:40]

• Keith Olbermann catalogs a series of alleged illegal acts by Donald Trump in the White House, including:

  • Deploying thugs and military against dissenting states (“Nothing Trump has done in sending in thugs and military... is legal.” [01:54])
  • Using Stephen Miller to intimidate state governors (specifically Gov. Pritzker, Illinois).
  • Instituting policies targeting Hispanics described as “ethnic cleansing,” with raids, deportations, and kidnappings.
  • Sending “election monitors” to blue states, interfering with state voting.
  • Accepting funds from international sources for personal gain and facilitating foreign influence operations.
  • Military actions without Congressional authorization, e.g., sending battleships to Latin America, ordering killings in international waters.
  • Undermining House and Senate authority, and joking about being both Speaker and President.

• Call to Action:

  • Urgent demand for blue state governors to withhold federal tax payments to the national government until Trump resigns.
  • Quotes “no taxation without representation” and urges governors to take legal responsibility to shield civilians from federal prosecution.

• Notable Quote:

  “We must have a state-led tax payment boycott… It is essential that governors like Newsom and Pritzker and Hochul … protect their citizens who are being subject to taxation without representation and without democracy.” ([07:30])

• Olbermann’s Motivation:

  • Argues that economic measures are currently the only effective check on Trump.
  • Acknowledges potential global economic turmoil but deems it preferable to an unchecked dictatorship.

2. The Kaleidoscope of Trump Outrages & The Ark Joke

[15:40–21:30]

• Olbermann reflects on the difficulty of keeping up with Trump’s daily stream of outrageous statements and actions.

• Ridicules Trump's claim of "building an ark," mocking the President’s confusion between “ark” and “arch” and the absurd fundraising for his projects:

  • “So you’re building an ark, huh, buddy? Okay, how many things a week does Trump say that would get anybody else in this country forcibly committed?” ([17:45])

• Ties the “ark” to broader corruption—Trump diverting funds, ballooning costs for private ballrooms and hangars.

3. Social Security, Obamacare Cuts, and International Intrigue

[21:30–25:45]

• Details cuts in Social Security (lower cost-of-living adjustments) and Trump’s version of Obamacare (massive cost increases).
• Accuses Trump of interfering in foreign elections (e.g., attempting to “buy” Argentina’s presidency for libertarian candidate Javier Milei).
• Critiques the deep state as “self-preserving,” pushing back against calls for moderation by Democrats:

  “The guy who says I will put Trump behind bars come hell or high water is the one who gets the nomination.” ([25:20])

4. Voter Intimidation and DOJ Election “Observers”

[25:45–31:26]

• Decries sending federal election monitors to Democratic-leaning counties in California and New Jersey as blatant intimidation, drawing parallels to Jim Crow.
• Details involvement of Trump DOJ’s Harmeet Dhillon (labeling her “10th rate lawyer”), and suggests that governors call out state National Guards to arrest federal “observers” if they attempt to intimidate or interfere.
• Mocks the rationale for sending monitors:

  “The irregularities are Republicans can’t win in those counties. There aren’t enough of them. This is how voting works. You have more votes, you win. The translation is we can’t win so we have to fix the election.” ([29:30])

5. Coverage of Graham Platner, CNN, and Nazi Symbol Controversy

[31:26–34:16]

• Discusses the scandal involving Maine Senate candidate Graham Platner, who tried to cover up a Nazi tattoo and was caught blatantly lying about it.
• Lambastes Platner’s dismissive reactions and calls for his renunciation by supporters, including Bernie Sanders.

6. Media Critiques: Fox News, CBS News, Right-Wing Audience Drift

[36:45–44:45]

• Satirizes TV executives’ belief that right-wing viewers can be moved from Fox to CBS; specifically, CBS’s rumored hiring of Fox’s Brett Baier as anchor:

  “It’s like deciding you’re going to move a river by picking up the water in the palms of your hands.” ([42:02])

• Recounts a sports media anecdote about ESPN2 and executives’ misjudgments, emphasizing the folly of trying to transplant entire audiences.

7. Media-Political Corporate Corruption

[44:45–48:00]

• Calls out Comcast/NBC and others for paying into Trump’s “ballroom” project to avoid prosecution, questioning whether such bribes are ethical, even if self-preservational.
• Critiques ABC, Disney, and CBS for failed moral leadership and cynical corporate behavior.

8. Bill Maher, Andrew Cuomo, and Hand-Waving Away Misconduct

[48:00–52:00]

• Roasts Bill Maher for endorsing Andrew Cuomo as “normal” and for downplaying Cuomo’s record of sexual harassment (“maybe he was a little too handsy, a little too Italian, a little too touchy”—mocked by Olbermann at [51:21]).
• Shares personal stories of being advised not to shake Maher’s hand prior to taping due to his alleged quirks.

9. Cheryl Hines on RFK Jr., Katie Miller, and Stepford Wives

[52:00–54:00]

• Lampoons Cheryl Hines (RFK Jr.’s wife) for her robotic defense of her husband’s integrity on Katie Miller’s podcast, likening her answers to “Stepford wife” responses.

10. Anna Paulina Luna’s Social Media Faux Pas

[54:00–56:20]

• Mocks Rep. Anna Paulina Luna for falling for a satirical account, Rep. “Jack Kimball” of California’s “54th district” (which does not exist), in a row about No Kings protest funding.
• Attributes her gullibility to a lack of knowledge, saying “54 is... double or triple her IQ.”
• Awards her “worst person in America” distinction in this segment.

11. “Worst Persons in the World” Segment

[36:45/After Commercials; Main segment highlights]

- Tied for Bronze:

• ICE in D.C.: A man was arrested for playing Darth Vader's theme (Imperial March); Olbermann delights at the ACLU's Star Wars-tinged legal brief (“the law might have tolerated government conduct of this sort a long time ago in a galaxy far, far away…” [37:00]).
• Kayleigh McEnany: Mocked for her upbeat reporting about Hamburger Helper sales as an indicator the economy is fine (“People are starving to death already. Isn’t that great? And you helped.” [38:54])

- Runner-Up:

• Anna Paulina Luna for the “Jack Kimball” debacle.

- “Winner”:

• Andrew Cuomo, for a xenophobic attack on a likely NYC mayoral opponent, suggesting he would “be cheering” a 9/11 recurrence (54:00+), and for generally destroying the Cuomo family name.
• Olbermann’s verdict:

  “I think to say this about somebody who is likely to be the next mayor of New York indicates a total lack of responsibility or interest in anybody alive except himself. I think he should go to hell.” ([56:10])

12. Extended Anecdote: Piazza, Clemens, and the Shattered Bat

“Things I Promise Not to Tell” [56:18–end]

• Olbermann recounts in detail his proximity to and coverage of the infamous 2000 World Series moment when Yankees pitcher Roger Clemens threw a piece of broken bat in Mike Piazza’s direction.
• Details on-field confusion, interactions with players and coaches, and why he didn’t ask Clemens about the incident first in a postgame interview (to avoid Clemens walking away).
• Recalls obtaining part of the broken bat from a Mets clubhouse attendant (“You gonna bring back garbage? Throw it out, keep it, whatever, what do I care?” [1:08:10]), subsequently being threatened with a lawsuit by Piazza in the press, but never directly in person—only to later attempt, unsuccessfully, to give the bat back for charity.
• Shares strange interactions with Piazza, his agent, and Red Sox owner John Henry—each time the bat returned, Piazza’s behavior got odder, insisting he wouldn’t sign or acknowledge the artifact.
• Concludes with his bemused frustration at Piazza and the bat’s odd afterlife, the only rational actor being the Yankees’ strength coach:

  "Which means that on top of everything else, Jeff Mangold is smarter than John Henry and I put together." ([1:19:05])

Notable Quotes & Moments (with Timestamps)

• On state tax resistance:

  “It is time to cut him off financially, to take the one measure that will force an end to this Trumpian madness… Stop transmitting federal taxes from the states to the national treasury until Trump resigns as President.” (Olbermann, [06:40])

• Absurdity of Trump regime:

  “Trump is now a rogue dictator... And the only thing that works in America right now, money used as a weapon must be used to freeze him where he stands...” (Olbermann, [11:55])

• On media executives’ folly:

  “It’s like deciding you’re going to move a river by picking up the water in the palms of your hands.” (Olbermann, [42:02])

• On “deep state” myths:

  “There is a deep state. It is not nefarious. It is simply self-preserving.” (Olbermann, [25:00])

• Mocking Anna Paulina Luna:

  "I know for people like Anna Paulina Luna, the number 54... might as well be the same as 294 million. It's an inestimably large number that's double or triple her IQ." (Olbermann, [55:39])

• On Andrew Cuomo’s NYC mayoral comments:

  “I think to say this about somebody who is likely to be the next mayor of New York indicates a total lack of responsibility or interest in anybody alive except himself. I think he should go to hell.” (Olbermann, [56:10])

Segment Timestamps

• Opening Rant/Special Comment: [01:47–21:30]
• Voter Intimidation & DOJ Election “Observers” [25:45–31:26]
• Media Critiques, Brett Baier Story, Sports Media [36:45–44:45]
• Worst Persons in the World: [36:45–56:20]
• “Things I Promise Not to Tell”: Clemens/Piazza Bat and Aftermath: [56:18–end]

Tone and Style

• Language: Blunt, sardonic, at times profane (“That’s how effing crazy this asshole is.”)
• Attitude: Incendiary criticism of Trump and the political/media establishment.
• Humor: Self-deprecating; sharp lampooning of public figures' stupidity and duplicity.
• Personalization: Olbermann’s anecdotes infuse the show with unique, first-person storytelling.

Conclusion

Keith Olbermann uses this episode to sound a sustained alarm against what he terms the Trump dictatorship, laying out an uncompromising case for economic resistance and state defiance. His commentary is interlaced with media industry insights, comedic takedowns, and a legendary sports anecdote illustrating both absurdity and the impermanence of public crisis. For listeners new or old, the episode captures Olbermann’s particular blend of politicized urgency, media critique, and human quirk.

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