Countdown with Keith Olbermann – "DONALD TRUMP: THAT'S 'DONALD' WITH 47 L's"

Podcast: Countdown with Keith Olbermann
Episode Date: December 15, 2025
Host: Keith Olbermann

Episode Overview

Keith Olbermann’s December 15, 2025, episode focuses chiefly on Donald Trump’s escalating string of political defeats (“Ls”), dissecting the reasons for his ongoing losses and their repercussions within the Republican Party and the nation. Olbermann uses his signature blend of political analysis, sarcasm, and cultural anecdotes to hammer home the sense of unraveling and dissent on Trump’s team, in the GOP at large, and across the American political landscape. The show also touches on broader media notes, the ongoing Epstein files controversy, a segment on sanitized children’s books (specifically Roald Dahl), and his classic "Worst Persons in the World."

Key Discussion Points & Insights

Trump's Relentless Losing Streak

[02:44]

• Trump is mired in a 27-day losing streak, with multiple blows including special elections, party dissent, damaged relationships, and failed policy pushes.
• Quote (04:04): "We are facing almost certain defeat, says the purulent face of the RNC, Joe Gruters, about the midterms. ... This is a pending, looming disaster headed our way."
• Olbermann details that not only Democrats but even staunch Republicans and Trump’s own advisors are acknowledging the crisis.
• Trump continues to mock the issue of “affordability” in campaigning, despite stern warnings from his own economists about its political toxicity.
• Notable Election Losses: Democrat Eileen Higgins’ decisive victory in Miami’s mayoral race and the GOP losing a fortified red seat in Georgia (06:45).

Internal GOP Conflict & Policy Failures

[06:45]

• Indiana’s GOP challenges Trump, with officials rebuffing his threats over federal funding tied to redistricting, exposing cracks in his party control.
• Quote (07:16): Olbermann on handling failure: "When your blackmail, blackmail fails. Don't advertise that it's failed. ... And when you realize ... and you try to bury your advertisement, don't go back and advertise it again."
• Trump’s efforts to reshape the justice system stall as even GOP senators (John Thune and Chuck Grassley) resist his push to kill “blue slips” and the filibuster (08:25).

Healthcare, Economy, and Broken Promises

[08:52]

• Trump fails to advance a viable healthcare plan; flirts with fringe ideas like buying insurance at Amazon or Sam’s Club (09:06).

• His tariffs and economic boasts ring increasingly hollow; even he admits to the Wall Street Journal he doesn’t know “when all this money is going to kick in” (11:46).

  "Asked whether Republicans would lose the house in November, Trump said, quote, I can't tell you, I don't know when all of this money is going to kick in." – (11:46)

Gun Violence & Atrocity Response

[12:23]

• Trump attempts to claim credit for identifying the suspect after the Brown University shooting, but blunders – the real killer was not yet identified.

• Olbermann criticizes the president’s prioritization of credit over empathy: "You've stepped on your tiny dick again. While millions mourned... you [claim credit]." (12:43)

• Chris Murphy’s critique (14:08): Trump’s policies and rhetoric deliberately fan the flames of violence in America.

  "Trump has been engaged in a pretty deliberate campaign to try to make violence more likely in this country. ... You’re going to see the results of that on the streets of America." – Sen. Chris Murphy (14:08)

The Epstein Files & Scandal Mechanics

[15:06]

• The release of photos of Trump with Jeffrey Epstein reignites scandal. The actual images are “nothing,” but the fight to keep them secret raises speculation and prolongs the story.
• The analogy to the Clinton-Lewinsky scandal and the drip-drip nature of modern scandals: "It doesn’t have to be a good scandal to be a gripping scandal. It just has to have new stories every day." (17:04)

Republican Media & Influence Meltdown

[17:36]

• Even conservative media is turning on Trump; Peggy Noonan’s Wall Street Journal column is titled "Trump may be losing his touch."
• Noonan on Trump’s fractured base: "Outside Washington, Mr. Trump's base is fighting with itself. America First is saying, I'm not MAGA. Conspiracies all over..." (19:09)
• With border issues “resolved,” Trump loses his most potent culture war lever.

Media Notes: CBS News’ Embarrassing Bari Weiss Experiment

[20:04]

• Bari Weiss’s Town Hall – edited, hosted, and starring Weiss – is a commercial disaster for CBS, attracting only bargain-basement advertisers (brands like Chia Pet, SuperBeets, and Carfax).
  • Sarcasm: “Congrats Barry Weiss ... you’ve turned CBS News into overnights on superstation WTBS in 1976.” (23:10)
• Other media anecdotes skewering recent notoriety bubbles (Olivia’s tell-all flop).

“Worst Persons In The World” Segment

[32:25 – 37:44]

• Honorable mentions:

  • Rep. Anna Paulina Luna: Ties to Russian influencers, pro-Kremlin talking points.
  • Gov. Josh Shapiro: Criticized for “both-sides-ing” political violence, despite being a direct victim of right-wing extremist attack.

• Winner: Howard Lutnick, Trump advisor, for his contradictory economic claims about U.S. production and iPhone manufacturing, flip-flopping to fit the narrative (36:21):

  "In April, Howard Lutnick promised that Trump’s America would be where millions of us would be screwing in little screws to make iPhones. By December, he is promising that Trump’s America will be where millions of us will not be screwing in the little screws to make iPhones. The arrogance ... is seriously astonishing." (37:39)

Notable Quotes & Memorable Moments

• "Then if that wasn’t clear enough, there’s no sugarcoating it. This is a pending, looming disaster headed our way." — Keith Olbermann quoting Joe Gruters, RNC (04:22)

• "He looks, well, what's the opposite of impregnable? He looks pregnable. And there are multiple, multiple Ls." — Keith Olbermann (07:50)

• "Trump’s health care plan fell in the Senate. Maybe he can find a new one on Amazon." — Olbermann (09:17)

• "He is turning this place into a shithole country. The Trump Ls are everywhere." — Olbermann (10:04)

• "It doesn’t have to be a good scandal to be a gripping scandal. It just has to have new stories every day." — Olbermann (17:04)

• "The right wingers tried to burn you to death and you are acting like this guy [Charlie Kirk] was St. Charlie ... preach all the 'condemn political violence' sermons you want, Governor, but ... do not join the 'both sides' parade." — Olbermann in “Worst Persons” (34:00)

Timestamps for Major Segments

| Timestamp | Segment | |-----------|---------| | 02:44 | Trump’s Losing Streak & Analysis | | 06:45 | Indiana GOP Defiance, Internal Republican Losses | | 08:52 | Policy Failures: Healthcare & Economy | | 12:23 | Gun Violence & Trump’s Missteps Post-Brown University Shooting | | 14:08 | Senator Chris Murphy’s Response | | 15:06 | Trump & Epstein Files – Scandal Dynamics | | 17:36 | Media/Influence Meltdown & Noonan’s Critique | | 20:04 | Media Notes: Bari Weiss’s Town Hall Flop | | 32:25 | Worst Persons in the World Segment | | 41:18 | Roald Dahl Segment – Censorship & Legacy | | 55:26 | Olbermann’s Personal Correspondence with Roald Dahl | | 56:22 | Reflections on Dahl, Literature, and Contradiction |

Roald Dahl Segment: On Literary Sanitization

[41:18 – 59:30]

• Olbermann critiques the “sensitivity reader” trend editing iconic works (e.g., Roald Dahl’s), comparing it to Orwellian erasure and shallow profit-driven censorship rather than thoughtful adaptation.
• He shares personal anecdotes about being a kid who wrote to Roald Dahl—and received letters back, including wisdom about poetry, ambition, and creative encouragement.
• Quote (55:26): "He had written more books than me. ... Olmen's parents later told the local newspaper that the letter had given the boy the kick of his young life."

Tone and Style

Throughout, Olbermann delivers a sharp, mocking, yet reflective take on politics, media, and cultural shifts. He combines biting sarcasm, pop culture references, and self-aware storytelling, using both personal anecdote and journalistic rigor to connect with listeners.

Conclusion

Keith Olbermann’s December 15, 2025 episode is a scathing dissection of Donald Trump’s ongoing public failures and the cracks appearing in his political and media machinery. The tone is irreverent yet pointed, connecting today’s headlines to longer arcs of American politics, scandal mechanics, and cultural change. His recurring theme is that Trump’s losses—political, institutional, reputational—are rapidly mounting, noticed even by his traditional supporters and enablers. The episode's latter half mixes a sentimental and critical look at the rewriting of beloved children’s literature, ending on a hopeful note about the enduring complexity of people, art, and culture.

For First-Time Listeners

This episode encapsulates Olbermann’s style: incisive political muckraking, no-holds-barred critique, pop culture riffing, and the occasional deeply personal or historical aside. It's accessible even to those unfamiliar with the recent headlines—he sets the context, draws the larger picture, and makes it entertaining as well as informative.