Countdown with Keith Olbermann – “TRUMP IS DROWNING” (12.18.25)

Podcast: Countdown with Keith Olbermann
Host: Keith Olbermann
Episode Date: December 18, 2025
Episode Title: TRUMP IS DROWNING

Overview

In this episode, Keith Olbermann delivers his scathing analysis of Donald Trump’s rapidly deteriorating presidency as 2025 comes to a close. Centering on plummeting poll numbers, political blunders, internal leaks, and the fallout from damning statements by Trump’s chief of staff Susie Wiles, Olbermann presents what he calls a “remarkable week” defined by chaos, incompetence, and a pervasive sense of drowning in scandal and failure. Woven into his political commentary are Olbermann’s signature segments: personal anecdotes from his career, “Worst Persons in the World” roundup, and sharp-tongued observations on current events and media figures.

Key Discussion Points and Insights

1. Trump’s Presidency “Drowning” – Approval and Political Failures

Timestamps: 02:26–08:51

• Cratering Poll Numbers:

  • Trump hits a new low with just 38% approval in a Marist poll, described as "[h]is worst number this term. Worst overall since 2018" (04:18).
  • Notable breakdown: Approval on the economy is only 36%, with a mere 33% trusting Republicans on economic matters. Major demographic groups now registering strong disapproval, including rural Americans, non-college-educated white women, and suburban voters (04:44).

• Legislative Embarrassment:

  • Republicans forced a vote to extend Obamacare subsidies against Trump’s wishes.
  • “So much failure, so many Ls, so little time to cackle.” (02:42)

• Foreign Policy Gaffe in Venezuela:

  • Trump tries a “wag the dog” move, sending an American armada to surround Venezuela, but Olbermann points out the absurdity: “Did you park a battleship on the border with Brazil? Donnie, you flatulent moron.” (03:22)
  • Trump’s justification vacillates between narcoterrorism and oil theft, mockingly called out by Olbermann.

2. Susie Wiles and Selective/Illegal Prosecutions

Timestamps: 08:51–20:42

• Susie Wiles Tapes and Legal Fallout:

  • Trump’s chief of staff, Susie Wiles, is recorded admitting to Trump’s vindictive impulses:
    • “I don't think he, Trump, wakes up thinking about retribution, but when there's an opportunity, he will go for it.” (09:18)
    • About Comey: “People could think it does look vindictive. I can't tell you why you shouldn't think that.” (09:23)

• Legal Implications:

  • Olbermann asserts that these taped admissions can be used to throw out all prosecutions against Trump’s political enemies—Smith, Comey, Fauci, Letitia James, Adam Schiff, et al.—and open the door to lawsuits for selective prosecution.
  • “Retribution means selective prosecution. And selective prosecution is illegal.” (09:39)
  • The magnitude: “That’s 465 other Trump victims this year alone. Everybody from Jerome Powell to Jimmy Kimmel, all of whom may now have some kind of legal case against Trump and his drowning arguments.” (10:36)

• Wiles’ Further Revelations:

  • She claims to have convinced Trump to limit his retribution efforts to the first 90 days of his second term—then notes that he reneged. This, Olbermann says, is “guilty foreknowledge” and “potential criminal charges for everybody who tried to enact vengeance for their Dracula in the White House.” (11:07)
  • Wiles on Trump: “He has the personality of an alcoholic… Trump doesn’t drink, but acts like he does. The alcoholic’s personality, complete with a view that there’s nothing he can’t do. Nothing.” (15:31)

3. Culture, Legacy, and Administration Sniping

Timestamps: 12:39–21:40

• Wiles vs. the MAGA World:

  • Wiles further launches broadsides at major players:
    • “J.D. Vance has ‘been a conspiracy theorist for a decade’ whose reasons for backing Trump are ‘sort of political’.” (13:58)
    • She calls budget director and “2025 Reich Marshall” Russell Vogt an “absolute zealot.”
    • Elon Musk is “an avowed ketamine user whose actions often leave her ‘aghast’ and ‘are not always rational.’” (14:25)

• Damage Control and Political Calculus:

  • Wiles’ evasive responses and lack of direct denial feed Olbermann’s thesis that the White House is “writing Trump off because he is drowning.” (18:42)
  • Olbermann explains her vanity, calculation, and the “fading Trump brain” as causes for such risky candor.

4. The “Rob Reiner Tweet” and Far-Right Disinformation

Timestamps: 21:45–26:32

• Fake Tweet and MAGA Backlash:

  • Trump’s allies circulate a blatantly fake, obscene tweet attributed to filmmaker Rob Reiner, with Olbermann ridiculing both the faker and the gullibility of Trump loyalists:
    • “It was kind of encouraging to see how many of his sheep were still appalled by what Trump wrote. But… the dumber ones had to try to rationalize Trump’s irrationality.” (22:40)
  • Laura Loomer is targeted: “...the Reiner tweet was of course a fake, just like Laura Loomer’s face.” (24:39)

• Right-Wing Deflection and Olbermann’s Rebuttal:

  • Jack Posobiec, Brett Weinstein, and Trump himself attempt to contrast reactions to the deaths of Charlie Kirk and Rob Reiner, with Olbermann clarifying:
    • “The killing of political commentators is indefensible. I believe this firmly.” (25:29)
    • “How are you comparing Charlie Kirk, who contributed nothing to this country, to Rob Reiner?” (26:06)

5. "Worst Persons in the World" Segment

Timestamps: 29:01–36:56

• Laura Ingraham:

  • Mocked for mistaking Ontario, Canada for a U.S. state in response to a Doug Ford announcement:
    • “Laura, Doug Ford is the premier of Ontario. Ontario, which is in Canada, which is a different country than ours.” (29:29)

• NYC Councilwoman Vicki Paladino:

  • Skewered for irrational claims on a shooting at Brown University, erroneously casting it as a targeted attack on Republicans:
    • “Like everything else in your life, Councilwoman, nothing at all is very clear.” (33:20)

• Philip "Cat Turd" Buchanan:

  • Ridiculed for conspiracy theories about the Brown shooter:
    • “Have you considered that for your own self, Philip?” (36:28)

6. Olbermann’s Trump Anecdotes – “Things I Promised Not to Tell”

Timestamps: 39:31–48:45

• 1983: First Encounter with Trump:
  • Trump was “weird, unsettling, unnatural… not really human and kinda drowning.” (39:36)
  • Olbermann recalls Trump’s “big fake smile” and describes Trump’s transactional view of life:
    • “The way he registers a sale with people, his receipt for convincing them to do his bidding: is their smile in return.” (41:12)
  • Remembers being creeped out: “That last guy we interviewed, Trump, what the f is wrong with that guy?” (47:35)

Notable Quotes and Memorable Moments

• On Venezuela Blunder:

  • “Donnie, you flatulent moron.” (03:22 – Olbermann mocking Trump’s claim of surrounding Venezuela)

• On Trump’s Dwindling Support:

  • “He’s even lost 5% of Republican approval in just the last month. Trump is drowning.” (05:34)

• On Susie Wiles’ Legal Leak:

  • “Retribution means selective prosecution. And selective prosecution is illegal.” (09:39)

• On Wiles Branding Trump:

  • “He has the personality of an alcoholic… Trump doesn’t drink, but acts like he does.” (15:31)

• On Trump’s Vanity Projects:

  • “The Trump Memorial Ballroom and Ego Storage airplane hangar… Now, $400 million. And oh, by the way, it opens in late 2028 and I hope the new president immediately tears it down. Put that on pay per view.” (06:34)

• On Political Reality:

  • “They are beginning to write Trump off because he is drowning, not only because it’s nearly 2026… It’s that she’s got to believe Trump will never actually see the article in Vanity Fair, or never actually see the actual quotes from it, will never read her say he’s got… the personality of an alcoholic, even though he supposedly agreed with her on that.” (18:42)

• On the Smile:

  • “His face went from an emotionless, almost lifeless, certainly non-human mask to a beaming, phony smile. That’s who he is. That’s what he thinks is his asset. An irresistible smile.” (41:30)

• Final Summation:

  • “I’ve done all the damage I can do here.” (47:43)

Major Segments: Timestamps Overview

• Trump’s Poll Troubles, Venezuela Gaffe: 02:26–08:51
• Susie Wiles Tapes and Legal Fallout: 08:51–20:42
• Wiles Attacks on Administration Figures: 12:39–21:40
• The Fake Rob Reiner Tweet: 21:45–26:32
• Worst Persons in the World segment: 29:01–36:56
• “Things I Promised Not to Tell” (Olbermann Meets Trump): 39:31–48:45

Tone and Language

Olbermann is characteristically acerbic, witty, and openly contemptuous of Trump and his circle. His analogies are colorful (“Trump is drowning on dry land”), his insults direct (“Donnie, you flatulent moron”), and his delivery maintains an urgent, sardonic pace. The episode brims with scorn, dark humor, and detailed, punchy analysis.

Summary for New Listeners

This episode is a must-hear for anyone following Trumpworld’s chaos in 2025 or interested in Olbermann’s unique blend of news analysis, political critique, and personal storytelling. Through scathing sarcasm and informed breakdown, Olbermann builds a compelling case for the Trump presidency being at “the tipping point,” battered by internal betrayals, legal jeopardy, and a crumbling political coalition. This is an episode where each segment lays groundwork for the central thesis: Trump, once buoyed by bravado and manipulation, is now unmistakably drowning.