Bulwark Takes: "Bill and Sarah Ask: How Bad Can It Get?"

Podcast: Bulwark Takes
Hosts: Bill Kristol & Sarah Longwell
Date: January 4, 2026
Episode Summary Prepared for Listeners

Episode Overview

In this special post-holiday edition of Bulwark Takes, Bill Kristol and Sarah Longwell grapple with the chaotic fallout from the Trump administration's military action in Venezuela. The sudden regime change, Trump's brash performance at his press conference, and the broader repercussions for U.S. foreign and domestic policy are central themes. In a conversation marked by both expertise and palpable anxiety, Bill and Sarah unpack what has happened, what it reveals about the current administration, and the ominous possibilities ahead for American democracy.

Key Discussion Points & Insights

1. The Venezuela Operation and Trump’s Response

[01:32 - 14:01]

• The hosts react in real time to news of the U.S.-led ouster of Nicolás Maduro and Trump's subsequent press conference, which Sarah describes as "jaw dropping."
• Both acknowledge that, while Maduro's removal is arguably positive, the lack of a clear post-invasion plan is deeply concerning.
• Trump reverses his traditional "no more foreign wars" stance by suggesting "boots on the ground are an option," contradicting his base and many administration allies.
• Bill and Sarah point out the irony of Trump now channeling neoconservative interventionism—a style he once derided.

"We're just staying in Venezuela, we're in charge now. Like, these are monumental things." — Sarah Longwell [03:20]

"He thinks we can just bluster and bludgeon people into doing what we want... I'm now very rattled in the sense that it's... I thought this could be anywhere between very mild positive to neutral to mild negative, honestly. And now I'm pretty worried that it could be pretty bad." — Bill Kristol [08:45]

• Trump publicly dismisses opposition leader María Corina Machado, raising further doubts about any democratic intention.

2. Lack of Strategy, Legal Questions, and Oil Motives

[12:10 - 17:41]

• The discussion highlights the administration's absence of a coherent strategy for Venezuela and hints at possible ulterior motives—specifically, securing oil resources.
• Bill calls Trump's oil argument "literally crazy" given present-day U.S. energy independence, drawing an unfavorable comparison to classic colonial resource grabs.

"Trump is explicitly saying, this is a war, we want the oil back... Nobody's talking about democracy. And so it is unclear, like, if we're just doing oil extraction, is that who we are now?" — Sarah Longwell [12:10]

• Sarah notes that similar arguments against “war for oil"—previously dismissed by many, including Bill—are now accurate in the Trump context.
• The legality of the operation is described as "gray territory," with Congress not yet mounting significant resistance. The administration appears to be relying on technicalities for bypassing the War Powers Act.

"Congress is not howling like I thought they might be about this. And so anyway, all I'm saying is that Trump is a criminal in all kinds of ways. I don't know that people saying this is illegal is going to get very far." — Sarah Longwell [25:51]

3. Dangers of Mission Accomplished Thinking

[17:41 - 22:46]

• The hosts repeatedly warn against premature triumphalism—likening Trump’s post-operation declaration to Bush’s infamous "Mission Accomplished" moment, except “12 hours” after the fact.
• They emphasize how easy it is to topple a dictator, but how fraught and perilous is the work of regime stabilization and nation-building.

"Everybody who's stating an opinion right now should just know that, like, all they did was the easy part. They did it well ... The hard part is what comes next. And they do not seem well equipped to do it, nor do they seem like they have a plan." — Sarah Longwell [20:55]

• Concerns are raised about domino instability in Latin America, refugee crises, and the possibility of future U.S. military involvement to stabilize chaos.

4. The Authoritarian Mindset and American Institutions

[22:46 - 30:06]

• Bill and Sarah reflect on the danger of presidential over-confidence and authoritarian impulses, noting Trump’s tendency to conflate domestic and foreign “intervention” (e.g., invoking National Guard deployments in U.S. cities and Venezuela in the same breath).

"It was chilling to me to see how connected in his head it was to basically go into American cities and do whatever he wants and how that in his mind was connected to just going into Venezuela and doing whatever he wants." — Sarah Longwell [28:06]

• Both hosts underscore the overestimation of American power and underestimation of the complexities inherent in regime change overseas.
• The discussion touches on the potential repercussions for democratic norms in the U.S.—particularly the precedent this sets for 2028 and the undermining of confidence in American elections.

5. Five Scenarios for America’s Trajectory (2026 and Beyond)

[30:06 - 44:19]

• Bill outlines five possible pathways for the country, ranging from "very good" to "very bad," based on the outcome of Trump’s presidency, public opinion shifts, and the prospects for Democratic victories.
  • Best case: Massive Democratic wins, public rejection of authoritarianism.
  • Neutral: Modest Democratic gains, significant but not transformative rejection of Trumpism.
  • Worst case: Entrenchment of Trumpism, Democratic Party failures, erosion of democracy.
• Sarah notes public opinion is heavily tethered to the economy and underscores the long-term importance of Trump’s declining popularity.

"If Trump's overall presidency is viewed as just a real failure politically, it's bad for the country, obviously, they have to recover from it. But we're in good shape in 28." — Bill Kristol [40:15]

• They agree Democrats must build a broad coalition and proactively address long-term challenges, including institutional weakness, demographic shifts, and structural disadvantages in the Senate.

6. Media, Messaging, and Power

[44:19 - 54:51]

• The conversation shifts to the rightward drift of mass media—highlighting takeovers of major networks and social media by Trump allies or sympathizers.
• Sarah stresses the need for Democrats to play offense, not just react, and to connect more viscerally with voters on matters like the economy, authoritarian excesses, and policy impacts.

"I need Democrats to have an offense mentality that isn't just reacting to Trump. And this is going to take a change in mentality..." — Sarah Longwell [48:41]

• Both agree that legal wrangling over the Venezuela mission’s legality isn’t where to win the public debate; rather, focus should be on impacts, injustice, and Trump’s "takeover" mindset.

Notable Quotes & Memorable Moments

Sarah Longwell:

• "My instincts from the before times create in me a sense of, oh, Maduro's a really bad guy. ... But then there's what I know now, which is that Donald Trump ... are to be trusted in no way for having a plan." [03:20]
• "Like, the pro... But then there's. So there's the before times where it's like objectively Maduro bad, him being gone. Good. But then there's what I know now..." [03:20]
• "It's jaw dropping listening to [Trump] throw Machado under the bus. ... This has nothing to do with democracy." [12:10]
• "The easy part is taking out the dictator. The hard part is what comes next. And they do not seem well equipped to do it, nor do they seem like they have a plan." [20:55]
• "You've got to look forward, right... While we look [at] Venezuela as a perfect example of them having no vision for where they're going, that means we have to have vision." [57:20]

Bill Kristol:

• "It's the disconnect between the bravado and the reality. We're going to run the country, we have no troops there." [07:04]
• "[Trump] really seems to have internalized the notion that we are really strong... that we can just basically go in, snatch them... and everyone's just gonna hop to it and do what we want." [24:52]
• "You could have the best outcome possible in 2028, and if you take over a country where you've got out-of-control DHS, a DOJ that doesn't have any memory of professional responsibility, and a military that's been corrupted... that's a very dangerous situation." [44:19]

Key Timestamps

• 00:00 – 01:32: Ads, intro
• 01:32 – 07:04: Trump’s Venezuela operation—initial reactions
• 07:04 – 14:01: Trump’s press conference, lack of planning, foreign policy incoherence
• 14:01 – 18:31: Oil motives, legal gray area, international/democratic implications
• 18:31 – 22:46: Mission accomplished fallacy, dangerous precedents
• 22:46 – 30:45: Authoritarian mindset, domestic parallels, future election risks
• 30:45 – 40:15: Five paths for America, importance of public opinion and the economy
• 40:15 – 47:54: Long-term coalition building, Senate challenges
• 47:54 – 54:51: Right-wing takeover of institutions, proactive vs. defensive strategies
• 54:51 – 58:50: Messaging, focus on policy excesses, vision for the pro-democracy coalition, closing thoughts

Tone and Style

Throughout the episode, Bill and Sarah maintain a tone of analytical urgency. Their conversation is candid, steeped in political experience, and frequently punctuated by both grim humor and exasperation at the administration's recklessness.

For New Listeners

This episode is essential listening for anyone trying to understand the stakes of ongoing foreign policy crises under the Trump administration, the risks posed to American democracy, and the urgent need for clear-eyed, forward-thinking opposition. The hosts weave together foreign and domestic policy, historical insights, and future-facing strategy in a discussion that spotlights both the dangers and the tools still available for democratic resilience.

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