The Lawfare Podcast: Rational Security: The “Caracas Like a Hurricane” Special Venezuela Edition

Release Date: January 8, 2026
Host: Scott R. Anderson
Guests: Benjamin Wittes, Natalie Orpet, Molly Roberts

Overview of the Episode

This special “Venezuela Edition” of Rational Security is dedicated to a historic and rapid U.S. intervention in Venezuela. The panel analyzes the Trump administration’s surprise decision to deploy special operations forces to capture Venezuelan leader Nicolas Maduro and its unprecedented consequences: bringing Maduro to New York for prosecution, leaving his deputy in charge, and initiating what may be a new American policy in the region.

The discussion explores the operation's legal, political, and foreign policy implications, with particular focus on why the decision was made, how it diverges from past interventions (notably Panama), the legal hurdles of prosecuting a former head of state, and what the U.S. really wants in Venezuela.

Key Discussion Points & Insights

1. Background: The U.S. Operation in Venezuela

• Trump’s Move: Over the holiday weekend, President Trump ordered special operations personnel into Venezuela to capture and extract Nicolas Maduro for prosecution in the United States. The administration insists this is a law enforcement—not a military—operation.
• Results: The operation was brief (2-3 hours), resulted in no American deaths, but over 70 Venezuelan fatalities. Maduro and his wife were brought to New York to face drug and weapons conspiracy charges.
• Aftermath: Trump asserts the U.S. will now “run Venezuela,” but keeps Maduro’s deputy Delsey Rodriguez in place, instead of the U.S.-recognized opposition, intending to use control over Venezuela’s oil as leverage.

Scott Anderson [05:11]:
“...the US Decision to intervene in Venezuela to capture Venezuelan dictator Nicolas Maduro, bring him to the United States for prosecution, and assert control over Venezuela...we're going to commit this whole episode to the Venezuela intervention and where it likely may lead.”

2. Comparing with Historic Precedents: Panama and Beyond

• Unlike Panama (1989), this was not a full-scale occupation. The U.S. targeted only the leadership, leaving much of the regime intact.
• Debate among panelists whether this “light touch” strategy is new genius or simply incoherent, with concerns about long-term efficacy.

Benjamin Wittes [09:42]:
“I think a lot of these questions, there's no evidence that I can see that they were thought through at all. On the one hand, this is being described as a law enforcement operation... There doesn't seem to have been a lot of thought to ... what happens to the rest of the regime. ... None of this makes a lot of sense.”

3. Inside the U.S. Decision Process

• The administration reportedly offered Maduro gilded exile in Turkey; his defiant public appearances allegedly pushed the U.S. to act.
• Multiple interests seem to have converged: oil, great power competition, drug trafficking indictment (pending since 2020), and immigration.

Natalie Orpet [15:31]:
“I wonder whether this is a reflection of a phenomenon we've seen in a lot of the administration's decision making...that have different interests and are pushing for things that happen to ... coalesce around an action that everyone agrees with, but for totally different reasons."

• The strike is bold, but Anderson argues it’s also risk-averse: “the minimal thing the Trump administration could do while still accomplishing what had become its publicly stated goal of removing Maduro from power.” [17:58]

4. International Law and Regional Risks

• Actions like stopping and boarding Russian-flagged vessels have global repercussions, threatening norms cherished even by rivals like China and Russia.
• The panel debates whether Trump’s posturing signals willingness for broader conflict or is simply a calculated threat to extract concessions in Venezuela.

Natalie Orpet [22:45]:
“...this is also not happening in a vacuum... The fact that it happened is instructive to states like Russia and China. ... you can see a world in which it starts just ratcheting up as a matter of broader foreign policy.”

5. The Prosecution of Nicolas Maduro

Legal Framework and Indictment:

• Charges: Narco-terrorism, conspiracy, cocaine importation, and weapons possession—expanded from a 2020 indictment.
• Allegations include using diplomatic cover for drug smuggling, corruption, and collaboration with designated terrorist organizations.
• Co-defendants: his wife, two high-ranking officials, a gang leader.
• The prosecution faces challenges regarding head of state immunity, official acts immunity, and the legality of Maduro's capture.

Molly Roberts [26:49]:
“There are four counts. They are narco terrorism, conspiracy, conspiracy to import cocaine and weapons possession... Some of them are about Maduro... glaringly, the indictment claims that he arranged for diplomatic passports for drug traffickers... It's not only Maduro who's named... So that's the basics of the indictment. But as you mentioned, there are a whole host of legal challenges...”

Irregular Rendition and Immunity Doctrines:

• U.S. precedent (Kerr-Frisbie doctrine) generally allows prosecution regardless of how a defendant is brought to the U.S., but 2nd Circuit’s Toscanino allows for a narrow exception (“shocking to the conscience”).
• The closest precedent is General Noriega (Panama) – but that was 11th Circuit law.
• No decisive case law for forcibly bringing sitting or former heads of state to U.S. trial in this manner.
• The defense will challenge jurisdiction, but both Natalie and Ben doubt these efforts will ultimately block prosecution.

Natalie Orpet [30:50]:
“There are a lot of questions here. ... this is not a settled area of law except to OLC, which believes that the President has the authority to do anything, including use the military to effectuate arrests... But that's not really established in the case law in a decisive way...”

Benjamin Wittes [38:51]:
“I will say the general proposition that you can render people from intelligence or military custody to the criminal justice system is an unremarkable proposition at this point... The Noriega case, as I recall, is all 11th Circuit law, which does not bind the 2nd Circuit...”

6. The U.S. Endgame in Venezuela: What Does “Running” Venezuela Mean?

• Trump administration leaves Delsey Rodriguez’s regime in place, not recognizing it but using oil sanctions and threats of force as leverage.
• Stated U.S. aims (per reporting): Crack down on drug flows, expel Iranian & Cuban operatives, stop oil sales to adversaries, and—eventually—allow free & fair elections (with a “flexible” timeline).
• Panelists agree the focus is transactional (oil, security), not ideological or about regime change for democracy’s sake—unlike neoconservative doctrine in Iraq.
• The move resembles historic “gunboat diplomacy,” prioritizing hard-power U.S. interests over institutional reform.

Molly Roberts [53:22]:
“US Officials have told Rodriguez they want her to crack down on drug flows, kick out Iranian, Cuban and operatives of other hostile countries or networks and stop the sale of oil to adversaries. ... Oh, and eventually facilitate free and fair elections and step aside, but flexible timeline for that. No imminent elections.”

Benjamin Wittes [54:29]:
“One important point here is how different this is from what we would think of as kind of neocon regime change. ... It’s a real kind of gunboat diplomacy attitude toward.”

• Anderson: “It just isn’t that ambitious an agenda... their ambitions are relatively limited, it kind of fits in with this idea, is that they just want the state to remain exactly as it is, the status quo with just a few small edits. And that’s a limited sort of action. It’s dramatic, it’s big... But that lack of ambition, the narrow targeted consequences, does make this in some ways like, like a more feasible plan.” [58:04]

Notable Quotes & Moments

• Scott R. Anderson, on the operation's novelty [01:51]:
  “We invite you to join members of lawfare team as we try to make sense of the week’s biggest national security news stories...with one particular development...That is...the US Decision to intervene in Venezuela...bring him to the United States for prosecution...”

• Benjamin Wittes on the administration’s thinking [09:42]:
  “None of this makes a lot of sense. ... The coherence of the theory of it didn’t make it work. Well, and so...sometimes you wreck bad things and the things that rise up to replace them are better...I think the short answer...is I don’t know.”

• Molly Roberts, summarizing the prosecution [26:49]:
  “There are four counts...The indictment claims he arranged for diplomatic passports for drug traffickers...It actually looks like a pretty normal serious indictment.”

• Natalie Orpet, on shifting legal doctrines [30:50]:
  “There is a doctrine called the Kerr Frisbee doctrine that...seems to say that no matter how you got to court...There is not a due process violation...But I think it is an overstatement to say that any such claims are decisively barred.”

• Panel quickfire contrast with Iraq [57:06]:
  Molly: “Joe Scarborough said that he talked to Trump this weekend and Trump said ... ‘the difference between the invasion of Iraq and the current operation was ... Bush didn’t keep the oil and we’re going to keep the oil.’”

• Stephen Miller’s worldview (as quoted by Molly Roberts) [57:46]:
  “We live in a world, the real world that is governed by strength...since the beginning of time. We can do what we want because we’re more powerful.”

• Benjamin Wittes, on the approach: [54:29]
  “This is a very different vocabulary. ... free and fair elections is last on the list as almost an afterthought with a flexible timeline. ... The demand is effectively we want our competition out of there and we want our hardest of hard power interests accommodated.”

Important Timestamps

• [06:23]: Introduction of main episode topics and approach.
• [08:18 – 17:39]: Deep dive into the surprise U.S. operation, historical analogies (Panama), and administration motives.
• [22:45 – 23:57]: Regional and international legal risks, especially vis-à-vis Russia and China.
• [26:49 – 44:04]: Detailed breakdown of Maduro’s indictment and legal hurdles for the prosecution in U.S. federal court.
• [49:00 – 61:30]: Discussion of the future for Venezuela and U.S. end goals.
• [54:29 – 58:04]: Comparison of Trump’s approach to neoconservative regime change, focus on “gunboat diplomacy,” and panel assessments.

Tone and Language

The podcast is analytical, irreverent, and detailed, combining deep legal insight with political analysis and a willingness to highlight ambiguity where answers are elusive. The panel consistently grounds discussion in precedent and law while highlighting the Trump administration’s break from both tradition and international norms.

Memorable Moments

• Name Confusion Openers: The episode opens with a lighthearted discussion about common names among the panelists, serving as comic relief before the heavy material.
• “Millerian Dialogue” [57:51]: The panel riffs on the Melian Dialogue from Thucydides to characterize Stephen Miller’s power politics worldview.
• Object Lessons [60:45+]: The panel closes with their “object lessons,” each providing a quirky recommendation or observation—ranging from New Yorker documentaries and artisanal golf putters to reflections on January 6th and meeting real-world figures from Lawfare’s reporting.

This episode offers a thorough, skeptical, and sharp-edged analysis of a potentially era-defining intervention. It does not shy away from highlighting legal gray areas, intellectual incoherence, or the stark, transactional bent of the current U.S. foreign policy—making it invaluable listening for anyone following Venezuela, U.S. national security, or the creeping return of 20th-century “gunboat diplomacy.”