Countdown with Keith Olbermann

Episode: TRUMP DEMENTIA: 14TH TIME HE'S CLAIMED GAS PRICES "JUST HIT $1.98"
Date: December 8, 2025

Overview

In this episode, Keith Olbermann focuses on Donald Trump’s repeated false claims about gasoline prices, using this as a launching point to question Trump’s cognitive abilities and stability. Olbermann frames these gaffes as evidence of “neurological disintegration” rather than mere political deception, vividly comparing the President to Drew Barrymore’s character in "50 First Dates." The episode critiques media coverage, the failures of officials like Merrick Garland, details developments in ongoing Trump-related investigations, and pokes fun at various political and media personalities via Olbermann’s trademark irreverence and sarcasm.

Key Discussion Points & Insights

1. Trump’s Repetitive Gas Price Lie as Evidence of Cognitive Decline

[03:01–08:46]

• Olbermann catalogs 14 separate occasions since April where Trump claimed gas had just hit $1.98 or $1.99 per gallon, always with feigned surprise.

• He compares Trump’s memory lapses to the film "50 First Dates," emphasizing the exasperating, potentially dangerous implications of such forgetfulness in a national leader.

• States that Trump "seems to be unaware that he is presenting this as something brand new" every time, rather than a recycled, debunked talking point.

• Links the origin of the $1.98 number to the price of unblended gasoline (which is not what consumers buy), highlighting Trump’s misunderstanding and fixation.

  "It's the goddamned Adam Sandler Drew Barrymore movie, '50 First Dates'...Only this is the President of the United States, not Drew effing Barrymore." (Keith Olbermann, 03:43)

  "Here we have, in real time, evidence of Trump’s dementia." (Keith Olbermann, 07:09)

2. The Media’s Tepid Coverage and Pipe Bomb Arrest

[09:34–11:33]

• Notes the arrest and confession of a January 6 pipe bomber, a 2020 election denier, and criticizes mainstream media for minimizing the story.

• Mocks right-wing conspiracy theories previously floated by figures like Glenn Beck and Dan Bongino about the pipe bomb incident.

  "If that had been anything but another lunatic under the delusion that Trump actually won the 2020 election...the media instead skated past it like it didn’t effing matter." (Keith Olbermann, 10:17)

3. Signs of Trump’s Deteriorating Behavior: The Pile Driver Anecdote

[11:33–12:18]

• Shares a report about Trump ignoring First Lady Melania’s complaints about incessant construction noise near the White House for amusement.

  "Sorry, darlin, that's progress. Trump said he told her, unquote." (Keith Olbermann, 12:05)

4. Jack Smith & Congressional Hearings: Accountability Blocked

[12:38–19:51]

• Outlines Trump’s ongoing legal exposure and the House’s looming closed-door hearing with Special Counsel Jack Smith.

• Expresses skepticism about meaningful outcomes, noting the GOP’s obstruction and its possible boomerang effect for figures like Jim Jordan.

• Sharp critique of Judge Eileen Cannon’s delays and favoritism toward Trump in his classified documents case, referencing details from Carol Lennig’s reporting.

• Excoriates Attorney General Merrick Garland for excessive timidity and lack of urgency in prosecuting Trump.

  “The further away we get from Jack Smith’s prosecution of Trump, the more we understand that Merrick Garland will go down in history as one of the great and most damaging idiots in our history.” (Keith Olbermann, 14:03)

  "If it was anybody else, we would arrest him tomorrow, Edelstein said knowingly." (Keith Olbermann quoting Julie Edelstein, 17:08)

5. Spoiler Candidates: A Warning Against ‘Fake’ Liberals

[19:51–25:53]

• Shifts focus to third-party and independent candidates (Jill Stein, RFK Jr., Cornell West), whom Olbermann claims are funded by right-wing interests to siphon votes from Democrats.

• Riffs on Stephen A. Smith’s purported exploration of a presidential run, lampooning his lack of political acumen with a flurry of sports/politics mix-ups.

  “I think he is a tool...Stephen A. Smith is a MAGA billionaire’s idea of somebody who would appeal to left wing voters. But happily for democracy, Stephen A. Smith is a moron.” (Keith Olbermann, 21:11)

  "If sports Stephen A. Smith were doing one of his phony debate shows with Politics Stephen A. Smith...there would be nothing left of Politics Stephen A. Smith..." (Keith Olbermann, 25:30)

6. Geopolitics, Russia, and America’s Weak Institutional Response

[25:53–31:21]

• Highlights the dysfunction of Trump’s approach to the Ukraine crisis and lays out the threat of Russian and Indian government complicity, calling for a much stronger Western response.

• Argues forcefully for the creation of a formal Democratic “shadow government” akin to the British model, to provide a credible and proactive voice for the opposition.

  "We need a shadow democratic government in this country now...because the official government of this country isn’t any good at anything anymore." (Keith Olbermann, 30:57)

7. The “Worst Persons in the World” Segment

[36:18–42:07]

• Bronze: Vince Shlomi (“ShamWow Guy”) for running for Congress as a Texas GOP candidate.

• Runner-up: Bari Weiss, new head of CBS News, mocked for “running out of anchors."

• Winner: Jake Tapper, for hypocrisy surrounding Trump and Biden’s mental acuity, and for downplaying Trump’s repeated sleep incidents.

  “Jake. Jake. You’re a whore, Jake. And a hypocritical one. Tapper today’s other worst person in the world.” (Keith Olbermann, 42:07)

8. Sports Segment: Sports Owners’ “Losses”

[45:38–55:54]

• Investigates Hal Steinbrenner’s claim that the New York Yankees may not have turned a profit, eviscerating the idea by showing the team’s astronomical valuation.

• Tells a classic anecdote about Dodgers owner Walter O’Malley’s creative (misleading) accounting, illuminating how sports owners often define “losses.”

  “So the next time you hear the owner of a sports franchise...tell you it or he has, ‘lost $1170 billion,’ just remember this is almost always Walter O’Malley math.” (Keith Olbermann, 55:15)

Memorable Quotes

• On Trump’s cognitive failings:

  “He blurts out in shock and excited surprise this same God damned thing an average of once every two weeks.” (03:33)

• On the stakes:

  "It is a nightmare. And it is proof that invoking the 25th Amendment is imperative and won’t happen." (08:09)

• On Merrick Garland:

  "If Trump went after Merrick Garland and tried to put him behind bars. I wouldn’t lift a finger to stop him." (19:00)

• On media figures:

  “Never fire your anchor of the CBS Evening News before you hire your new anchor…Who you gonna get? The slapjob guy? ... Who are you gonna get, Barry? The disinterred ghost of Walter Cronkite, CBS News?” (39:19)

• On “shadow government”:

  "We need a shadow government in this country for more than one reason, and one reason more than any other, because the official government of this country isn’t any good at anything anymore." (30:57)

Notable Segment Timestamps

• Opening theme/main commentary begins: 03:01
• Trump’s gas price repetition and breakdown: 03:01 – 09:34
• Pipe bomb story/media critique: 09:34 – 11:33
• Trump’s pile driver anecdote: 11:33 – 12:18
• Jack Smith, Garland, DOJ failures: 12:38 – 19:51
• Third-party politics and Stephen A. Smith: 19:51 – 25:53
• Geopolitical threats & the need for shadow government: 25:53 – 31:21
• Preview of “Worst Persons” segment: 36:18
• Worst Persons in the World (Shlomi, Weiss, Tapper): 36:38 – 42:07
• Sports Segment (Yankees and sports owner story): 45:38 – 55:54

Tone

The episode is marked by Olbermann’s signature blend of biting sarcasm, wit, and pointed political commentary. He pulls no punches in his denunciation of Trump, the legal and media apparatus that enables him, and the performative futility of America’s current political opposition. Anecdotes and historical references are intertwined with acerbic humor and liberal use of expletives.

For Those Who Haven’t Listened

This episode is a rapid-fire Olbermann political commentary session, interlacing deep frustration, dark humor, and media criticism. He uses the case of Trump’s repeatedly false gas price claim as a symbol of broader cognitive and systemic decay—both in the person of Trump and across American institutions. The episode is a blend of news, analysis, satire, and anecdote, delivered with impassioned urgency. If you want a succinct, unfiltered, and highly opinionated recap of recent political screw-ups—this is it.