Deadline: White House – “Day 25 of the War with Iran”
Host: Alicia Menendez (in for Nicolle Wallace)
Date: March 24, 2026
Episode Overview:
On the 25th day of the war between the United States and Iran, Alicia Menendez leads urgent, insightful conversations about the war’s military, political, and economic developments. With a panel of heavyweight analysts and guest Senator Tim Kaine, the episode unpacks both the failures of the Trump administration’s strategy and the ripple effects at home and abroad. Major themes include the lack of coherent U.S. strategy, diplomatic deadlock, the administration’s energy policy reversals during a global energy crisis, congressional responses, and a deepening crackdown on the free press.
Main Themes & Purpose
- Examine the dire and chaotic state of the US-Iran war.
- Highlight warnings from former military leaders against a strategy-less military campaign.
- Analyze the Trump administration's motives and approach, particularly its shift toward seeking an off-ramp.
- Explore the war’s domestic impacts: rising gas prices, agency funding crises, and contentious energy policy decisions.
- Investigate constitutional challenges facing the media and public access to government actions.
Key Discussion Points & Insights
1. War with Iran: Battlefield & Diplomatic Stalemate
[01:04–02:46] Overview of War Status
- Iranian missile and drone attacks persist despite President Trump’s claims of “obliteration.”
- Oil prices soar; the economic toll mounts domestically and globally.
- Former Defense Secretary Jim Mattis and General Stanley McChrystal warn the administration has achieved tactical wins but lacks a pathway to strategic success.
- Gen. McChrystal: “Targetry never makes up for a lack of strategy.” (01:45)
- Mattis: “We’re in a tough spot when it comes to forcing Iran to reopen the Strait of Hormuz and ease the oil crisis.” (01:33)
[02:46–04:20] Critique of Trump Admin Approach
- Trump reportedly weighs “regime decapitation” and handpicking Iran’s next leader, as done in Venezuela—yet no signs this is viable or strategically sound.
- Gen. McChrystal: “This idea of decapitating the regime ... It wouldn’t have that effect on me.” (02:28)
- Arab mediators express skepticism; U.S. explores diplomatic channels through Turkey, Egypt, and Pakistan but with limited Iranian signals of interest.
2. Lack of Strategy & Strategic Objectives
[04:20–06:39] In-depth Expert Analysis
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John Brennan: Echoes Mattis and McChrystal, asserting military victories do not equal lasting outcomes.
- “The US military can do phenomenal work ... but it’s no closer to a settlement if we don’t have any other movement on more fundamental issues, such as the nuclear program, the Strait of Hormuz, regime repression...” (04:37)
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Alicia and Brennan discuss the near-impossible task of retrofitting a strategy onto an already-escalated conflict.
- “It’s really, really difficult to do that now … You’re not going to achieve your strategic objectives unless there is some type of engagement with the Iranian regime.” – John Brennan (05:43)
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[06:39–07:15]
- Brennan: Trump was almost certainly warned of the long-term dangers and uncertainties going into military action.
3. Diplomatic Moves: Who is Talking and What’s the Real Motive?
[07:15–10:34] Behind the Scenes Diplomacy
- Michael Crowley (NYT): Current diplomatic environment is confused, with conflicting statements from President Trump about who is negotiating (mentions of Marco Rubio, Kushner, Witkoff). Genuine talks remain uncertain.
- “Who do we not see a lot of evidence of a desire to want to talk and make a deal from right now? ... That’s the Iranians.” (09:40)
- US allies—Egyptians, Pakistanis, Turks—are reportedly mediating, motivated by oil price shocks and fears of global economic collapse.
4. Trump’s Leadership Style & Implications for Negotiation
[10:34–13:09] Critique of Trump’s Motivation and Method
- Anne Applebaum: "He doesn't think strategically... He doesn't have a big plan. What he thinks about is what’s good for him ... I think at this point he’ll do almost anything.” (11:03)
- John Brennan (echoing): “It’s more akin to tiddlywinks in terms of individual moves without a sense of the second, third, and fourth-order effects...” (12:26)
[13:09–14:26]
- Alicia: Trump seeks a “Venezuela style solution” by picking a future Iranian leader, but this is unworkable given Iran’s theocratic structures.
- Brennan: “There’s no real separation of church and state ... Handpicking somebody ... would be inconsistent with what Iranians have done for the last 47 years.” (13:46)
5. Lessons from the Past: Asymmetric Warfare
[14:26–17:53] Strategic Complexity and Asymmetric Threats
- Gen. McChrystal’s NYT interview (clip):
- “If you like this war, enjoy this first part, because this is the best part, because everything after this will be harder ... Iranians can create enough of a hazard just by, say, hitting a tanker once a week.” (14:35)
- Applebaum: Trump fails to grasp that “the Iranians themselves have agency ... The world isn’t a game of Risk ... that's really not how it works.” (16:25)
6. Contradictory Policy: Escalation vs. Exit
[17:53–21:08] Dissonance between De-escalation and Military Action
- Reports surface of Trump considering both aggressive escalations (seizing Kharg Island, ground operations to secure uranium) and seeking rapid exit.
- Michael Crowley: Highlights dilemma—Trump’s lack of prior planning for critical issues like Iran’s nuclear materials leaves him improvising with costly options.
7. Advising the President: What Should the Off-Ramp Be?
[21:08–21:55]
- John Brennan: Advises a “pause in the fighting to prevent further deaths” and warns there is “no off-ramp… going to validate his justification for the war, nor ... save political face.” Recommends pivot to diplomacy.
8. Domestic Fallout: DHS Shutdown and TSA Lines
[24:06–27:52] DHS Funding Crisis and Congressional Wrangling
- Senator Tim Kaine criticizes Trump’s vacillation and Republicans for the DHS shutdown affecting TSA, Coast Guard.
- “We worked out a funding deal ... Take yes for an answer ... The ones who aren't being paid should be paid. And we've been saying to Republicans, take yes for an answer.” (25:19)
- Kaine resists any ICE funding without reforms, pushing for bipartisan-negotiated solutions that keep public agencies functioning.
9. Congressional Oversight and “War of Choice” Funding
[27:52–30:51]
- Kaine decries the administration’s lack of transparency and Congressional input, especially regarding potential $200 billion funding requests for the war:
- “They only want to do hearings in classified because they ... don't want to subject administration officials ... to being asked questions in front of the American public. That shows how insecure they are...” (29:45)
- Warns the war’s economic and human costs will not dissipate even if bombing stops today.
10. Energy Policy Irony Amid Crisis
[32:49–37:48] Trump’s Rollback of Renewable Energy
- Trump cancels major offshore wind projects, paying a French company ~$1B in taxpayer funds to instead back fossil fuel investments, even as war-fueled energy crisis escalates gas prices.
- Alicia Menendez: “Those wind farms... would have produced clean, cheap, renewable wind power, the kind that can't get stuck in the Strait of Hormuz...” (33:05)
- Justin Wolfers: “The president's case against wind are literally the rantings of an old man. I've seen Grandpa Simpson make more sense ... This is non-scientific, doesn't make sense, non-economic and doesn't serve the American people.” (34:12)
- Sam Stein: “Donald Trump has taken away some of the tax incentives that would have helped the [EV] industry along ... basically conceded the field to China.” (35:18)
- Justin Wolfers: “If you look seriously, what is it that makes some countries rich and other countries poor? ... It's these long term investments. It's these institutions. ... [Authoritarianism] tends to undermine the level of GDP by about 10%... a generation later.” (37:48)
11. Press Freedom & Administration Retaliation
[39:07–44:07]
- After losing a court battle, the administration moves to restrict media access at the Pentagon further.
- Sam Stein: "They're trying to radically transform ... the confines of the First Amendment. ... You have to fight for it ... [or] they will inevitably win through attrition." (40:22)
- Angela Corazon: The administration defines itself by its enemies, sees no value in cooperating with the press, and falls far short of the “First Amendment protector” branding some supporters once hoped.
Notable Quotes & Memorable Moments
- Gen. Stanley McChrystal: “Targetry never makes up for a lack of strategy.” (01:45)
- John Brennan: “It’s more akin to tiddlywinks in terms of individual moves...” (12:26)
- Anne Applebaum: “He doesn't think strategically. ... He’s looking for a solution that makes him at the center and makes him a victor. And I think at this point he’ll do almost anything.” (11:03)
- Sen. Tim Kaine: “We worked out a funding deal with Republicans ... let's fund all the agencies at the levels you agree with except for ICE, where we need serious reforms.” (25:19)
- Justin Wolfers: “The president's case against wind are literally the rantings of an old man. I've seen Grandpa Simpson make more sense.” (34:12)
- Sam Stein: “Donald Trump has taken away some of the tax incentives ... and basically conceded the field to China.” (35:18)
- Justin Wolfers: “Electing an autocrat or bringing to power an autocrat tends to undermine the level of GDP by about 10%. ... The effects of all this really are yours and my kids are gonna wake up in a world and there'll be a set of inventions that were never invented.” (37:48)
Important Segment Timestamps
- 00:00–01:04: Ads & episode transition
- 01:04–02:46: War status update; military warnings
- 04:20–07:15: Brennan analysis; warnings ignored
- 07:15–10:34: Crowley on diplomatic confusion
- 11:03–13:09: Applebaum and Brennan on Trump’s leadership
- 14:35–17:53: McChrystal’s lessons from asymmetric wars
- 24:06–27:52: Sen. Kaine on DHS & agency funding crisis
- 27:52–30:51: Kaine on war oversight, costs
- 33:05–37:48: Wind policy, energy crisis, and long-term consequences
- 39:07–44:07: Trump administration vs. press freedom
Conclusion
This episode delivers a comprehensive, sobering analysis of how America’s lack of war strategy in Iran, ad hoc decision-making by the Trump administration, and erosion of institutional norms—both at home and abroad—have sparked crises at every level. With sharp commentary, well-supported reporting, and warnings from voices across politics and public service, it’s a crucial listen for understanding the depths and dangers of current American governance.
(End of summary. Non-content sections, ads, and promos omitted.)