Rational Security – "Caracas Like a Hurricane" Special Venezuela Edition
Podcast by The Lawfare Institute | January 8, 2026
Panelists: Scott R. Anderson (Host), Benjamin Wittes, Natalie Orpet, Molly Roberts

Episode Overview

This episode of Rational Security dedicates a deep-dive discussion to the stunning recent U.S. intervention in Venezuela. Host Scott R. Anderson is joined by Lawfare colleagues Benjamin Wittes, Natalie Orpet, and Molly Roberts to dissect the Trump administration’s shock decision to send U.S. special forces into Caracas, capture Venezuelan leader Nicolas Maduro, and bring him for prosecution in New York. The episode explores the operation's legality, the ensuing prosecution, and the unclear future for Venezuela’s government—with reflections on international norms, the administration’s motives, and the potential fallout.

Main Discussion Themes & Key Points

1. The U.S. Intervention in Venezuela: What Happened?

Segment Start: [05:29]

• The Operation:

  • Last weekend, President Trump authorized a special operations mission to capture dictator Nicolas Maduro—threatened for months but still a shocking, "two to three hours long" raid ([07:25]).
  • Over 70 Venezuelans killed, no reported U.S. fatalities.
  • White House frames this as "law enforcement," not war.
  • Trump immediately announced intention to “run Venezuela," yet left Maduro’s deputy (Delcy Rodríguez) in charge, but without formal U.S. recognition ([07:25], [45:52]).

• Comparisons:

  • Panelists note essential differences from U.S. Panama invasion (1989-90), which entailed massive troop presence, occupation, and regime installation ([07:26]).

• Motivation and Logic:

  • Ben Wittes [08:49, 12:00]:
    • “I think a lot of these questions, there’s no evidence I can see that they were thought through at all.”
    • The operation appears rushed, driven by diverse, conflicting interests in the administration—oil, anti-narcotics, law enforcement legacy.
    • “There doesn't seem to have been a lot of thought to...what happens to the rest of the regime.”

• Notable Quote:

  • Ben Wittes [12:00]:
    • “None of this makes a lot of sense...It is not obvious to me what the mechanism of that is.”

2. Decision-Making Inside the Trump Administration

Segment Start: [13:29]

• Internal Dynamics:

  • Natalie Orpet and others suggest the move resulted from several shifting pressures: oil interests, immigration policy, regional “sphere of influence” ambitions, and a longstanding DOJ indictment ([14:38], [16:46]).
  • DOJ’s criminal case against Maduro dates to 2020; the move may result from coincidental alignment of disparate goals, not grand strategy.

• Notable Quote:

  • Natalie Orpet [14:38]:
    • “[A] convenient confluence of people who wanted to take action against Maduro for wildly different reasons.”

• Panel Reflection:

  • Scott Anderson highlights the relatively “conservative” nature of the operation—a “snatch and grab” rather than a massive engagement ([17:05]).
  • Discussion on whether the Trump administration has real tolerance for broader escalation or prefers symbolic shows of force.

3. Risks, International Precedents, and Potential Escalation

Segment Start: [19:22]

• Panel Split:
  • Ben Wittes raises the question: Is Trump’s approach “regional hegemony at all costs,” or is there a risk-averse side to his administration ([19:22])?
  • Natalie Orpet warns about setting global precedents—U.S. actions may embolden Russia/China to intervene forcibly in their own regions ([21:52]).
  • Tensions rise as U.S. military stops and boards a Russian-flagged oil vessel—potential for wider confrontation ([23:04]).
  • "There’s definitely a risk here...if all these risks are a sign that the Trump administration is the mad dog it claims to be in international affairs." – Scott Anderson [23:04]

4. The Extraordinary Prosecution of Nicolas Maduro

Segment Start: [25:56]

• The Charges:

  • Four main counts: narco-terrorism conspiracy, conspiracy to import cocaine, and two counts related to weapons possession ([25:56]).
  • New indictment in SDNY supersedes 2020’s, naming Maduro’s wife, top officials, and a cartel leader as co-conspirators.

• Legal Barriers & Immunity:

  • Head-of-state and official act immunity could be argued, though U.S. doesn’t recognize Maduro as a legitimate head of state ([25:56]).
  • Molly Roberts:
    • “There are a whole host of legal challenges...One of them...is head of state immunity, and...official acts immunity. And then...the illegality of his arrest and transfer.” ([25:56])

• Irregular Rendition & Precedent:

  • U.S. has forcibly “rendered” foreign defendants before (e.g., Noriega), but rarely with an ostensible head of state ([29:05], [35:43]).
  • The “Ker-Frisbee” doctrine generally allows prosecution despite the manner of transfer; "Toscanino" carve-out could come into play if treatment was egregious, but unlikely to save Maduro ([35:02]-[40:56]).

• Panel’s Prognosis:

  • General agreement that, despite some room for litigation, Maduro is likely to be tried:
    • Benjamin Wittes [35:56]: “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…”

• Choice of Venue:

  • Curiosity around why charges were brought in SDNY, not Florida; likely a result of momentum from the 2020 indictment ([40:56]).

5. What Comes Next for Venezuela? “Running the Country” by Remote?

Segment Start: [45:52]

• Recognition and Power:

  • U.S. leaves Delcy Rodríguez’s government in place—but continues to treat it as illegitimate. Political vacuum remains ([45:52]).
  • Trump and surrogates threaten further action, but stress "quarantining" oil exports and leveraging sanctions and military threats ([45:52]).

• Unclear and Modest Aims:

  • Natalie Orpet:
    • Suggests the administration’s demands are "out-of-the-box": oil control, diminishing influence of adversarial actors (Iran, Cuba), narcotics crackdown, and eventual “free and fair elections”—though with no set timeline ([47:19]).

• Notable Quotes:

  • Molly Roberts [50:14]:
    • “Reporting...is that US officials have told Rodríguez they want her to crack down on drug flows, kick out Iranian, Cuban...operatives...and stop the sale of oil to adversaries. Oh, and eventually facilitate free and fair elections and step aside but [with a] flexible timeline for that.”
  • Ben Wittes [51:21]:
    • “It’s a real kind of gunboat diplomacy attitude...it couldn’t be more dissonant with the tone of the more recent advocates of regime change in different countries.”

• Comparisons to Other Regime Changes:

  • Panel draws sharp distinctions to previous U.S. interventions (e.g., Iraq), which were couched in terms of democracy promotion and international legitimacy.
  • Trump (per Joe Scarborough call) told allies the "difference" with Iraq is "Bush didn’t keep the oil and we’re going to keep the oil." ([53:58])

Notable Quotes & Memorable Moments

• On the intervention’s unexpectedness:

  • “I did not see this one coming.”
    – Benjamin Wittes [04:32]

• On administrative chaos:

  • “A convenient confluence of people who wanted to take action against Maduro for wildly different reasons.”
    – Natalie Orpet [14:38]

• On oil and gunboat diplomacy:

  • “It’s a real kind of gunboat diplomacy attitude...And it couldn’t be more dissonant with...more recent advocates of regime change in different countries.”
    – Benjamin Wittes [51:21]

• On candid priorities:

  • “Trump...said the difference between the invasion of Iraq and the current operation was, quote, unquote, that Bush didn’t keep the oil and we’re going to keep the oil.”
    – Molly Roberts [53:58]

• On legal barriers:

  • “There’s a whole host of legal challenges that Maduro could raise...head of state immunity...and then...the illegality of his arrest and transfer...”
    – Molly Roberts [25:56]

• On global risks:

  • “The fact that it happened is instructive to states like Russia and China. So if either...choose to take similar action on a theory of ‘you did it first’...”
    – Natalie Orpet [21:52]

Important Timestamps

• 05:29 – Start of discussion on U.S. special operation in Venezuela
• 08:49 – Ben Wittes analyses the mission’s incoherent planning
• 14:38 – Natalie Orpet on decision-making chaos
• 17:05 – Scott Anderson: Was this really “bold”?
• 21:52 – Risks of global precedent and escalation
• 25:56 – Details on the indictment and legal hurdles
• 29:05/35:02 – Panel digresses into U.S. practice of 'rendition' and relevant precedent
• 45:52 – How the U.S. government is handling post-Maduro Venezuela
• 51:21 – Gunboat diplomacy and oil at the center of U.S. demands

Tone and Style

The discussion is brisk, erudite, often skeptical, and sprinkled with wry humor and self-effacing asides. The panel is frank about knowledge gaps and brings a mixture of legal expertise, historical analogies, and biting contemporary commentary. Notably, the group is skeptical of both the wisdom and the consistency of Trump administration actions, but also wary of dismissing them as merely incompetent.

Useful for Newcomers

This episode provides a thorough, accessible primer on the U.S. intervention in Venezuela—its context, operational details, legal and diplomatic challenges, and possible consequences. The conversation is well-structured, attributed, and objective, making it valuable even for those who have not followed the events closely.