The Bulwark Podcast
Episode Title: Bill Kristol: Trump Wants Troops in Portland
Air Date: September 29, 2025
Host: Tim Miller
Guest: Bill Kristol
Overview
In this episode, Tim Miller and Bill Kristol provide in-depth analysis of the latest political moves by the Trump administration, focusing on threats to liberal democracy, the militarization of domestic politics, escalating tensions in Portland, and the implications of recent executive actions. The conversation covers the politicization of the military, foreign policy maneuvers (particularly concerning Venezuela), partisan narratives around mass shootings, intra-party Democratic challenges, and economic policy contradictions—all with the Bulwark's signature mix of urgency, skepticism, and wit.
Key Discussion Points and Insights
1. Trump’s Gathering with Generals at Quantico
(00:51–07:07)
- Trump is set to address 800 generals and flag officers at Quantico alongside Secretary of Defense Pete Hegseth. The event's purpose and optics are scrutinized.
- Kristol suggests it's a deliberate, ominous effort to align the military with Trump’s agenda, "sending the signal down to the troops, to the public that the military is on board with Trump's agenda—that agenda, including blowing up boats in the Caribbean and use of troops domestically" (02:14, Kristol).
- They question why the event is held at Quantico instead of the Pentagon, noting it may be about removing generals from their support bases, putting them in a more controlled, isolated situation, and potentially intimidating them.
- Both argue that military leaders should resist being used as political props and hope their public comments will encourage critical thinking among those attending.
2. The Purpose and Risks of the Military Event
- Tim Miller notes the potential for a loyalty test: "Let's have a gathering of [the generals]. Let's see who's loyal, let's see who think we think might be a troublemaker so we can kind of get rid of anybody that's not fully on board" (05:24, Miller).
- Kristol agrees, noting the real risk is political intimidation and the message that it’s "Trump’s military, not the United States military" (06:34, Kristol).
3. Federal Troops and Protests in Portland
(07:07–12:52)
- Discussion shifts to Trump’s actions in Portland—ordering military deployments around the ICE facility amid minimal actual unrest.
- Miller notes, "To me, this one is a little bit more ominous than even kind of the suggestions of sending [troops] into my own city in New Orleans...I do wonder if they're kind of champing at the bit for a conflict here and they maybe see Portland as an opportunity" (08:08, Miller).
- Kristol highlights the contrast between rhetoric and reality: the actual situation is calm, but Trump is "busy conflating the video from 2020 with the video from today" to justify force and normalize federal military deployments against domestic protests.
- Kristol's warning: "He's moving right down the path we all saw coming. I think, honestly, that he wants to make normalize this, not just in L.A., not just in D.C. but in Portland and Memphis and elsewhere" (09:31, Kristol).
4. Media Coverage and Political Calculus
(10:29–11:40)
- The hosts are critical of media normalizations, describing coverage that presents the administration’s desire for more unrest as a win-win political strategy—a perverse incentive structure.
5. Politicization, Selectivity, and Optics
- Tim voices skepticism that the warzone narrative about Portland will stick ("I don't think Portland is war zone", 11:40) but acknowledges the city’s reputation as a flashpoint in the culture war.
6. National Security Memorandum (NSPM-7) and Executive Orders
(13:12–15:01)
- Kristol explains the legal context and dangers of recent executive actions combining the War on Terror with domestic surveillance and crackdowns, targeting groups based on thin or ideological evidence—a "very fast slope."
- Quote: "It's a very fast slope when you read the presidential memorandum and also the executive order basically going after protected speech because it might have something to do with something Stephen Miller thinks shouldn't be happening in the US" (14:12, Kristol).
7. Venezuela, Bombing Drug Boats, and Political Opportunity
(15:01–19:17)
- Discussion of reports on possible U.S. strikes in Venezuela and their domestic political utility.
- Kristol argues these foreign interventions are performative: "They're trying to create a fake kind of war situation partly to legitimize what they're doing at home" (15:44).
- Miller urges Democrats to seize this as an issue, exposing the GOP’s double standard and reclaiming the anti-war mantle: "This is an opportunity to say... we are the responsible party when it comes to foreign policy, that you cannot trust these guys..." (17:15, Miller).
- Both agree Democrats can campaign as both strong and responsible on defense.
8. Mass Shootings and Partisan Narrative Failures
(19:37–27:34)
- The weekend’s mass shootings highlight the perils of partisan, selective coverage—right-wing and left-wing media amplify convenient motives, ignore inconvenient ones.
- Miller: "If you look at it the first way, there's kind of no solution to it... If you look at it... we need to deal with veterans’ mental health, ...with red flag laws ...at least something we could move together as a society" (23:41, Miller).
- Kristol points out genuine policy issues (mental health, veterans’ support, gun access) and laments the political system’s ineptitude in fostering honest dialogue.
9. Media Misinformation and Demonization of Minorities
- Miller recounts an exchange with a right-wing editor who falsely blamed trans people for mass shootings, highlighting systemic media bias and its damaging consequences.
- Kristol calls out presidential-level demagoguery: "We've never had a president...who just has gone after a vulnerable small community in this way and obliterated any possibility of a sensible discussion of the real policy issues" (26:34, Kristol).
10. Government Shutdown and Democratic Messaging Challenges
(27:34–31:47)
- Upcoming Trump-convened White House meeting with Congressional leaders is critiqued as a political setup favoring Trump's optics.
- Miller and Kristol express concern over Democrats’ lack of messaging confidence and strategic clarity in opposing Trump’s unpopular measures, especially regarding ICE and military funding.
11. Hakeem Jeffries, Eric Adams, and New York Politics
(31:47–36:10)
- Miller critiques Jeffries’ seemingly unnecessary statement of support for Eric Adams amid corruption problems, arguing Democratic leaders must focus on more consequential battles.
- Kristol: "How serious can one take them when they say we really stand against the Trump administration, the rule of law? Well, not so much...when they're okay with Eric Adams" (33:10).
12. Trade War, Farm Bailouts, and “MAGA Communism”
(36:10–39:16)
- Miller rants against Trump’s damaging trade war, which resulted in lost soybean markets and subsequent farmer bailouts paid for by consumer tariffs.
- "It is just an absolutely insane and maddening policy and people should be pissed about it... It is in addition to stupid policy. It is a direct affront to the, to the America first ethos" (38:08, Miller).
- Kristol: "Xi is taking Trump to the cleaners... the Democrats...could be tougher on China than Trump" (38:28).
13. TikTok Deal and Cronyism
(39:16–41:41)
- Criticizes the forced sale of TikTok to politically connected MAGA billionaires at an undervalued price, likening it to "swampy, weak, not America first handout to his friends."
- Allegations of behind-the-scenes corruption and the potential for censorship/manipulation.
14. Upcoming Governor Races in Virginia and New Jersey
(41:41–44:02)
- Spanberger’s likely victory in Virginia and a tighter-than-ideal race for Sherrill in New Jersey signal opportunities and warning signs for Democrats.
15. Democrats’ Senate Map and Ideological Purity Fights
(44:02–48:53)
- Ezra Klein’s suggestion that Democrats run candidates appropriate for red states (even socially conservative ones) is discussed. Miller and Kristol agree that expanding the map and being pragmatic is essential to securing Senate control.
- Miller: "Shitposting Ezra Klein on Twitter is not the answer. Like, trying to find a model that works is" (47:56).
Notable Quotes & Memorable Moments
-
On Political Weaponization of the Military:
"This is a little more ominous...sending the signal down to the troops, to the public that the military is on board with Trump's agenda."
– Bill Kristol (02:14) -
On Loyalty Tests:
"Let's have a gathering...Let's see who's loyal, let's see who think we think might be a troublemaker so we can kind of get rid of anybody that's not fully on board."
– Tim Miller (05:24) -
On Portland Deployments:
"He's moving right down the path we all saw coming. He wants to normalize this."
– Bill Kristol (09:31) -
On Executive Overreach:
"It's a very fast slope...basically going after protected speech because it might have something to do with something Stephen Miller thinks shouldn't be happening..."
– Bill Kristol (14:12) -
Democrats’ Opportunity on Foreign Policy:
"This is an opportunity to say...we are the responsible party when it comes to foreign policy, that you cannot trust these guys..."
– Tim Miller (17:15) -
On Mass Shooting Narratives:
"The way that this news is being processed in our society...makes further examples of this more likely rather than...us trying to address the real causes."
– Tim Miller (21:55) -
On Media and Minorities:
"We've never had a president...who just has gone after a vulnerable small community in this way and obliterated any possibility...of a sensible discussion of the real policy issues..."
– Bill Kristol (26:34) -
On “MAGA Communism”:
"It is just an absolutely insane and maddening policy and people should be pissed about it...It is a direct affront to the America first ethos."
– Tim Miller (38:08) -
On Senate Strategy:
"Shitposting Ezra Klein on Twitter is not the answer. Like, trying to find a model that works is."
– Tim Miller (47:56) -
Comic Relief: Triple Sabotage at the UN
"Triple sabotage. That's a great term, isn't it? Reminds me...double secret probation..."
– Bill Kristol (50:11)
Timestamps for Important Segments (MM:SS)
- Quantico event analysis: 00:51–07:07
- Federal troops in Portland: 07:07–12:52
- Executive orders and civil liberties: 13:12–15:01
- Venezuela and foreign policy: 15:01–19:17
- Mass shootings/media: 19:37–27:34
- Democrats’ messaging/government shutdown: 27:34–31:47
- Democratic leadership/NY politics: 31:47–36:10
- Trade war/farm bailouts: 36:10–39:16
- The TikTok deal: 39:16–41:41
- 2025 governor races: 41:41–44:02
- Senate strategy/political purity: 44:02–48:53
- Comic close – “triple sabotage”: 49:23–50:51
Tone and Style
The episode mixes sober, analytical concern about the threat to American democratic norms with the Bulwark’s signature sarcasm and biting humor. The conversation is peppered with asides, personal anecdotes, and banter, especially in the final segment.
Summary for Non-Listeners
This episode is a must-listen for those interested in the contemporary challenges facing American democracy under Trump: the deliberate politicization of the military, alarming executive overreach, misleading media narratives, and the Democrats’ ongoing struggle to mount an effective opposition. It provides both a critical diagnosis of the moment and concrete proposals for action—plus a necessary dose of gallows humor to help you “wash down the crazy.”