Armed Conflict Foreign Relations & International Law

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

Scott R. Anderson, Natalie K. Orpett, Molly Roberts, Benjamin Wittes
Thursday, January 8, 2026, 12:30 PM
Scott Anderson sat down with Benjamin Wittes, Natalie Orpett, and Molly Roberts for a special deep-dive into the intervention in Venezuela.

This week, Scott sat down with his Lawfare colleagues Benjamin Wittes, Natalie Orpett, and Molly Roberts for a special deep-dive into the intervention in Venezuela, including:

  • “A Hop, Skip, and Jump Across the Rubicon.” This past weekend, the Trump administration took the step that Trump has been threatening for months: he deployed special operations to capture Venezuelan dictator Nicolás Maduro and bring him to the United States for criminal prosecution. The targeted operation was only hours long and resulted in no American fatalities, though more than 70 people in Venezuela were reportedly killed. The Trump administration has described it as a “law enforcement” operation. But what was it really? And where did he get the authority to do it?
  • “A Truly Extraordinary Rendition.” By Monday, Maduro and his wife were in New York being arraigned on an array of drug- and weapons-related conspiracy charges. But prosecuting a head of state—albeit one not recognized by the United States—presents certain unique challenges. How should we expect the criminal case to proceed? 
  • “Running in Place.” President Trump has asserted that he and his advisers are now going to “run” Venezuela. But he’s left Maduro’s deputy, Delcy Rodríguez, in place, in lieu of the opposition movement the United States and many other countries have recognized as Venezuela’s legitimate government. Trump and his advisers seem intent on dictating terms to Venezuela through the “leverage” provided them by the ongoing quarantine over Venezuela’s oil, and potentially the threat of additional military action. But can this light-touch strategy succeed? 

In object lessons, (notably Chicagoan) Natalie delights in her long-standing admiration of The New Yorker with Netflix’s documentary “The New Yorker at 100.” Molly approaches Trump’s takeover of D.C. golf courses with a pitch for Knotty by Nature’s wooden putters. Scott honors the 5th anniversary of the Jan. 6, 2021, attack on the Capitol with a recommendation of Ellie Silverman’s moving profile of Nathan Tate in the Washington Post. And Ben honors the same anniversary with both a revisiting of Lawfare's narrative podcast series The Aftermath, and, relatedly, a surprise interview by Holly Berkley Fletcher with one of the attack’s most infamous perpetrators. 

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Scott R. Anderson is a fellow in Governance Studies at the Brookings Institution and a Senior Fellow in the National Security Law Program at Columbia Law School. He previously served as an Attorney-Adviser in the Office of the Legal Adviser at the U.S. Department of State and as the legal advisor for the U.S. Embassy in Baghdad, Iraq.
Natalie Orpett is the executive editor of Lawfare and deputy general counsel of the Lawfare Institute. She was previously an attorney at the law firm Jenner & Block, where she focused on investigations and government controversies, and also maintained an active pro bono practice. She served as civilian counsel to a defendant in the Guantanamo Military Commissions for more than eight years.
Molly Roberts is a senior editor at Lawfare. She was previously a member of the editorial board at The Washington Post, where she covered technology, legal affairs and more, as well as wrote columns about everything from cryptocurrency grift and graft to panda diplomacy at the National Zoo.
Benjamin Wittes is editor in chief of Lawfare and a Senior Fellow in Governance Studies at the Brookings Institution. He is the author of several books.
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