The Bulwark Daily
The Bulwark Daily

Bill Kristol: Keep Up the Pressure, Dems

August 31, 2026

AI Summary

5 min read

In a single weekend, the Pentagon’s secret stable of online propagandists was exposed, Iran fired missiles toward Jordan, and the Trump administration announced it was taking a direct financial stake in a Venezuelan oil company run by a businessman who faced criminal investigations for money laundering. For Bill Kristol, editor at large of The Bulwark, this is not a collection of unrelated scandals. It is the predictable result of a Republican Party that has abandoned the pretense of good-faith governance, and it demands that Democrats stop playing prevent defense and start making Trump own what his administration is doing.

The failed war and the lies that sustain it

The conversation opens with the war in Iran, which Kristol and host Tim Miller describe as a catastrophe the administration is actively concealing. A recent leak to the Washington Post revealed that the heads of the Army, Navy, and Air Force, along with four-star commanders overseeing U.S. operations in Europe, Asia, and Latin America, have warned Defense Secretary Pete Hegseth that prolonging large-scale operations in Iran is unsustainable and is weakening America’s ability to confront threats elsewhere. The 50,000 troops stationed there are too many, and the strain is real.

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What you'll learn

  • 1 (01:37) **Opening & War Update: Iran Conflict Escalates** - Tim Miller and Bill Kristol set the table, discussing a new exchange of fire in the Strait of Hormuz and a leak about military leaders warning the war is unsustainable.
  • 2 (08:50) **The Venezuela Oil Deal: A New Imperialism?** - Tim and Bill analyze the reported US government plan to take a direct financial stake in a Venezuelan oil company, tying the US to an unelected government and a businessman with a criminal past.
  • 3 (17:52) **Pentagon Propaganda: Secretly Paying Online Influencers** - The hosts discuss the revelation that the Pentagon secretly hired conservative military veterans with large online followings to pose as independent commentators and amplify Hegseth's views.
  • 4 (25:45) **The CR Fight: Why Democrats Must Play Hardball** - The conversation pivots to the upcoming government funding fight, with Bill and Tim arguing Democrats should use every procedural tool to oppose the budget and highlight the administration's failures.
  • 5 (28:29) **Midterm Math: Trump Voters Having Second Thoughts** - The hosts analyze a UMass Amherst poll showing 1 in 6 Trump voters would change their 2024 vote, and discuss how this data should shape Democratic strategy.
  • 6 (34:57) **Trump's "Data Centers" Gift to Democrats** - Breaking news: Trump posts that communities should want data centers or risk being "backwards and poor," which the hosts see as a massive political opening for Democrats.
  • 7 (38:21) **Laura Loomer's Racism: A Test for Republicans** - The hosts use Laura Loomer's recent racist tweets as a foil to discuss the state of the GOP and why every Republican candidate should have to answer for her influence.

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Guests on this episode

Show Notes

Trump’s war is far from over, top military leaders are warning Hegseth that prolonged ops in the region are unsustainable, and Americans have been financing Pentagon propagandists who’ve been secretly collecting taxpayer money to try to convince us that things are going great in Iran. This is not the time for congressional Democrats to allow Republicans to easily pass a spending resolution that keeps the government open. At the same time, Trump keeps handing gifts to Democrats—like his sell-out to tech oligarchs and his praise of data centers. Plus: The Venezuelan oil deal is a socialist PR stunt, vile Laura Loomer is trying to bring back the normalization of Islamaphobia, Massachusetts voters should recall the risks of sending an 80-year-old back to the Senate, and Marco really is the worst Cabinet member of all

Bill Kristol joins Tim Miller.
show notes:

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