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Trump’s Been Bombing Boats in the Caribbean. Is This Legal?
“Of all the unprecedented actions Trump has taken in his second term, this might be the most extraordinary—and potentially the most dangerous,” writes Jed Rubenfeld. (Photo by Kevin Dietsch/Getty Images)
I thought the answer was an obvious no. It turns out to be much more complicated.
By Jed Rubenfeld
10.22.25 — U.S. Politics
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On September 1, President Donald Trump ordered an air strike on a speedboat in the Caribbean. The boat was obliterated. Eleven people were killed.

The next day, Trump proudly posted about it on Truth Social; he even attached a video. His post claimed that the people on board were “positively identified Tren de Aragua Narcoterrorists”—a reference to a notorious Venezuelan criminal organization—who were “transporting illegal narcotics” to the United States.

Since then, the U.S. has carried out at least seven more similar air strikes on alleged drug-smuggling boats in the Caribbean, reportedly killing at least 34 people. The eighth attack came late on Tuesday, according to a U.S. official. Where exactly these boats came from, and who exactly was aboard, is not publicly known. While claiming that the boats were running narcotics for foreign drug cartels, the administration has not said that they belonged to foreign governments, or that the people on board were state actors.

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Jed Rubenfeld
Jed Rubenfeld is a professor of constitutional law at Yale Law School, a free speech lawyer, and host of the Straight Down the Middle podcast. He is the author of five books, including the million-copy bestselling novel The Interpretation of Murder, and his work has been translated into over thirty languages. He lives with his wife, Amy Chua, in New York City, and is the proud father of two exceptional daughters, Sophia and Lulu.
Tags:
Donald Trump
Supreme Court
Law
Foreign Policy
Drugs
Latin America
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