Countdown with Keith Olbermann – September 11, 2025
Episode Title: TRUMP DOESN'T REALIZE RUSSIA HAS ATTACKED POLAND
Host: Keith Olbermann
Podcast: iHeartPodcasts
Date: September 11, 2025
Episode Overview
This episode of "Countdown with Keith Olbermann" delivers a forceful critique of former President Donald Trump’s response to a Russian drone incursion into Polish airspace, underscoring Trump’s incapacity for international crisis management and the potential global risks of such ignorance. Olbermann intertwines current political analysis with sharp commentary on recent acts of political violence in America (notably the murder of Charlie Kirk) and uses the anniversary of 9/11 to reflect on the evolution of American political culture, bipartisanship, and the persistent undercurrents of violence in U.S. history.
The episode also features Olbermann’s signature segments, including a historical James Thurber reading, a personal 9/11 anecdote, and the trademark “Worst Persons in the World” satirical roundup.
Key Discussion Points & Insights
1. Trump’s Failure During the Russian Attack on Poland
- (02:35) Olbermann opens with the critical news: Russia has sent drones into Poland’s airspace, testing the resolve of the U.S. and NATO.
- Trump’s public reaction is characterized as lackadaisical and ignorant, compared in mockery to Martin Sheen's messianic, apocalyptic president in “The Dead Zone.”
- Quote: “What’s with Russia violating Poland’s airspace? Seriously, asshole, that’s your job, you great decaying pile of burger grease.” (03:23)
- Olbermann emphasizes that American troops are stationed in Poland, underscoring the risk and gravity of the incident.
- Quote: “There are 10,000 American troops in Poland. Did you know that? What would have happened if mere debris...hit a US base?” (04:51)
Analysis and Escalation
- Olbermann suggests Putin’s actions are a direct test of Trump’s resolve as Commander-in-Chief, finding Trump totally unfit and unaware.
- “Not realizing Putin had attacked Poland, Trump just did his test marketing for an attempt to rebuild the 1980s Soviet Union.” (05:38)
- Both Putin and Netanyahu—other world leaders—have manipulated or tested Trump's ineptitude through proxy confrontations.
- “For the second time in two days, somebody Trump thinks is his friend...deliberately attacked an American ally.” (06:02)
- “Putin sent drones over his country this week. Just like the way Trump took the bribe of a free jet…then Netanyahu bombed Qatar this week.” (06:18)
The Deeper Threat
- Olbermann ties Trump’s incompetence to a larger global security risk: world leaders cannot trust Trump to respond to crises—deliberately or not.
- “A thousand problems with having a deteriorating low IQ narcissist as the leader of your country...but this is the real problem.” (07:54)
Historical Parallel
- An extended comparison is made to Chamberlain’s appeasement of Hitler and ultimate betrayal by the Nazi–Soviet pact, underlining Trump’s even lesser capacity.
- “We have a Chamberlain who doesn’t even have the presence of mind to shout ‘Great Scott’ when Putin attacks Poland.” (12:39)
2. The Trump-Epstein-Maxwell “Coverup” Developments
- Olbermann covers the latest on the Jeffrey Epstein–Ghislaine Maxwell saga, focusing on an attorney's recent CNN admission that Maxwell’s transfer to a more lenient prison was achieved via a "quid pro quo."
- Quote: “That’s the confirmation that Trump has already made a deal with Ghislaine Maxwell about the Epstein files.” (15:27)
- Discussion turns to a recently surfaced “birthday book” containing Trump’s signature, with Trump’s surrogates denying the authenticity despite compelling evidence.
- “A, it’s his signature. I’ve already posted my letter from Trump online—it’s the same signature.” (15:32)
- “The only dead issue around here is the naive belief that Trump isn’t the star of the Epstein files.” (18:06)
Political Stakes and Denials
- Olbermann notes Republicans’ awkward responses and attempts to suppress release of Epstein-related DOJ files.
- “Mike Johnson can manipulate the rules to prevent that vote...which will only inflame the case again.” (19:09)
- Absurd, Freudian slips and lack of supportive defenses from Trump’s inner circle highlighted for comic derision.
3. Reflections on Political Violence and Hypocrisy – The Charlie Kirk Murder
- (21:30) Transition to the murder of commentator Charlie Kirk, Olbermann denounces political violence but laments the hypocrisy and history of such actions in America.
- “My God, can we stop with the hypocrisy about this? This is America. All we have done for virtually all of our history is shoot political opponents.” (21:54)
- He notes gun violence has shaped politics from Hamilton onwards, and that both right and left lean on violence-laden rhetoric.
- “You can be utterly opposed to shooting people without repeating America’s age-old lie...that violence has no part in our political system. It is woven in as surely as the stars on the flag.” (24:53)
- Plays a quote from Kirk defending gun deaths as the “price” of the Second Amendment:
- Charlie Kirk (04/05/2023): “I think it’s worth to have a cost of unfortunately some gun deaths every single year so that we can have the Second Amendment...” (26:27)
- Olbermann demands honest reckoning with America’s embrace of violence and challenges listeners to real action, not clichés.
4. Signature Segment: “Worst Persons in the World”
Bronze: J.D. Vance (Vice President) & Commentator Jennifer Greenberg
- Vance is criticized for advocating military actions based on personal trauma; Olbermann is unsparing:
- “For J.D. Vance...I grieve about his mother. For J.D. Vance, Vice President...resign and turn yourself in to the International Court of Justice.” (35:12)
Runner Up: Andrew Klavan (Daily Wire Host)
- Klavan’s remarks on the Civil War and civil rights are ridiculed as Klan-adjacent.
- “‘So much of what is tyrannical in this country arose from the post-Civil War amendments...’ That subtext is the Ku Klux Klan and the National Rifle Association...” (36:41)
Winner: Jeff Shell (CBS/Paramount Executive)
- Olbermann tells personal anecdotes about corporate media execs’ bad faith, culminating in a sharp critique of Shell for facilitating Trump-aligned censorship at CBS.
- “Some men are born whores, some men achieve whoring and others have whoredom thrust upon them. And then there are creatures like Jeff Shell, whose best defense for betrayal is to publicly say, you should have known they were lying...” (45:17)
5. 9/11 Anniversary Reflections and “Things I Promise Not to Tell”
- (49:40) Olbermann share stories from the day and its aftermath, spotlighting the cumulative trauma and persistent legacy.
- Shares the “man who wasn’t there” story – Tomas Reyes, a former Cantor Fitzgerald employee spared on 9/11 by coincidence, reinforcing the randomness and heartbreak.
- “That was how Thomas Reyes was in the men’s room at the Red Eye Grill... and not at his desk in the World Trade Center.” (53:19)
On American Unity and Division Post-9/11
- Olbermann criticizes how Republicans, particularly President Bush, squandered the moment of national unity for political gain.
- “Nearly unanimous support of his government was granted... It can only be squandered by those who use it not to heal...but to take political advantage of them.” (59:38)
- He links the post-9/11 climate directly to the present divisive and authoritarian tendencies embodied by Trumpism.
- “The government in waiting of Trump uses 9/11, uses the hatreds of 9/11 as a wedge to pit Americans against Americans.” (62:30)
The Parable of “Twilight Zone: The Monsters are Due on Maple Street”
- To close, Olbermann invokes the “Twilight Zone” parable about how fear and paranoia destroy communities from within, warning that “prejudices can kill and suspicion can destroy…” (64:35)
Notable Quotes & Memorable Moments
- “What’s with Russia violating Poland’s airspace? Seriously, asshole, that’s your job...If you don’t know, get the F out.” – Keith Olbermann (03:23)
- "Trump...not realizing Putin had attacked Poland...just did his test marketing for an attempt to rebuild the 1980s Soviet Union.” (05:38)
- “We have a Chamberlain who doesn’t even have the presence of mind to shout ‘Great Scott’ when Putin attacks Poland.” (12:39)
- “That’s the confirmation that Trump has already made a deal with Ghislaine Maxwell about the Epstein files.” (15:27)
- “This is America. All we have done for virtually all of our history is shoot political opponents.” (21:54)
- “You will never live in a society when you have an armed citizenry and you won’t have a single gun death...I think it’s worth it.” – Charlie Kirk (26:21)
- “Some men are born whores, some men achieve whoring and others have whoredom thrust upon them. And then there are creatures like Jeff Shell...” (45:17)
- “That was how Thomas Reyes was in the men’s room at the Red Eye Grill... and not at his desk in the World Trade Center.” (53:19)
- “The tools of conquest do not necessarily come with bombs and explosions and fallout...There are weapons that are simply thoughts, attitudes, prejudices...” – Rod Serling/Olbermann (64:35)
Timestamps by Segment
- 02:35 — Introduction to Russia’s drone attack on Poland and Trump’s response
- 06:00–13:00 — Analysis of Trump’s failures and historical parallels to Chamberlain
- 14:50–19:30 — Epstein–Maxwell–Trump “quid pro quo” and Republican denials
- 21:30–28:08 — Charlie Kirk’s death, political violence, and American history with guns
- 32:11–47:03 — “Worst Persons in the World”: Vance, Klavan, Shell, and CBS media worries
- 49:40–58:31 — Olbermann’s “Things I Promise Not to Tell” – 9/11 personal stories
- 58:31–64:35 — Reflections on post-9/11 unity and division, Twilight Zone parable
Closing Thoughts
Olbermann’s episode powerfully blends his trademark sarcasm with historical allusion and urgent warnings about American political decline. Threaded throughout are reminders of America’s tendency for both self-destruction and moments of humanity. While the tone is deeply critical (and often scathingly funny), it is also a heartfelt plea for seriousness in leadership and a reckoning with the country’s violent past and present.