The Bulwark Daily
The Bulwark Daily

Jonathan V. Last: How Much Stupid Can We Possibly Take?

September 3, 2026

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5 min read

How Much Stupid Can We Possibly Take?

The Trump administration brokered an illegal oil deal with Venezuela using an Epstein-linked oligarch as an intermediary, the Department of Defense took a 35% equity stake in a state-owned company (which it cannot legally do), and the whole scheme was negotiated through a man who hired Rudy Giuliani to make federal investigations disappear. This is not a fever dream. It happened. And Jonathan V. Last, the Bulwark's editor and author of the Triad newsletter, came on the show to walk through it and a cascade of other stories that together raise a single unsettling question: how much more of this can the country absorb before something fundamental breaks?

The Venezuela Deal: A Coup by Oligarch

The oil deal is illegal on multiple levels. The Defense Department cannot take equity positions in companies—that's a rule designed to prevent the military from having independent funding, which is how militaries in other countries end up running things. Venezuela's own constitution, Articles 12 and 13, explicitly forbids foreign entities from touching national resources. None of that stopped anyone.

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What you'll learn

  • 1 (01:36) **Opening & The Rare Win** - Tim Miller celebrates a rare instance of an oligarch being punished for cheating and shouts out Pablo's investigation.
  • 2 (03:04) **Happy News: MAGA Pollster Predicts GOP Doom** - JVL and Tim discuss Rich Berris, a "big data Republican" and MAGA pollster, who predicts easy wins for Democrats in Texas and thinks Trump is screwing everything up.
  • 3 (05:27) **Trump's Insulting "Endorsement" of Ken Paxton** - Tim reads a bizarre Trump quote about Paxton, where Trump insults his appearance and dress while claiming he's a good Attorney General.
  • 4 (08:15) **The "Department of War": Tom Tillis' Hypocrisy on Hegseth** - Tim and JVL eviscerate Senator Tom Tillis for criticizing Pete Hegseth's incompetence after voting to confirm him as Secretary of Defense.
  • 5 (14:13) **Susan Collins' Delusional "Influence"** - The conversation shifts to Susan Collins, who claims she voted a certain way to retain "influence and impact," which JVL and Tim argue is the opposite of reality.
  • 6 (17:17) **The Venezuela Oil Heist: An Illegal Deal** - Tim pivots to JVL's newsletter about the Trump administration's illegal oil deal with Venezuela, facilitated by a shady oligarch named Alejandro Betancourt Lopez.
  • 7 (21:40) **The Oligarch, Rudy Giuliani, and the Coup** - JVL details Alejandro's history of currying favor with Maduro, hiring Rudy Giuliani to drop a US investigation, and becoming the backchannel for the coup.

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Show Notes

Thom Tillis was the pivotal vote to confirm a buffoon to run the Department of Defense, and now he’s shocked about Hegseth’s incompetency. JD wants everyone to know he’s a Catholic now, but he doesn’t seem to have absorbed even the basic teachings of Catholicism. And Susan Collins claims she has influence with her Senate colleagues over Trump’s agenda—even though on almost every occasion she has made sure that her vote won’t matter. Meanwhile, Trump did a coup in Venezuela with an associate of Jeffrey Epstein. Plus: Tim reads from the mailbag, Trump is repulsed by Ken Paxton, the Antichrist might be walking amongst us, and what would happen if armed, leftwing activists created a sanctuary space in Ohio to protect Haitian immigrants?

JVL joins Tim Miller.
show notes:

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