*** 11/16/25 - Dan Drezner - So How Is the Illegal War (in the Caribbean) Going?.................

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Buzz Sawyer

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Nov 19, 2025, 2:25:43 AMNov 19
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from substack post:
"The hard-working staff here at Drezner’s World has begun to notice a pattern in which the legal justification for a presidential action rests primarily on Donald Trump’s simply asserting something is true without any factual foundation. In the above example, it was the president declaring a national emergency over trade deficits, when no such emergency exists.

Now it seems that the president is doing this to justify a possible a possible invasion of Venezuela.
............................................................................................................................
The families of some of the killed fishermen vehemently deny that their relatives 
were narco-terrorists and have hired U.S. lawyers to sue the federal government.
 ..............................................................................................................................

So to sum up: the Trump administration is waging military airstrikes in the Caribbean that are clearly designed to rattle the leader of Venezuela into departing the political stage. Except that the legality of those airstrikes rest on dubious presidential assertions and the administration’s planning for Venezuela is preliminary at best. Oh, and all of this is super-unpopular with the American people.

My bet is that the Trump administration is attempting to run the same playbook in Venezuela that it attempted to run on North Korea in 2017 — take every action short of war possible to convince the other side to talk.¹ But this did not work with North Korea and there are reasons to doubt it will work on Venezuela."

The Trump administration keeps killing people in the Caribbean in the hopes of... what, exactly?
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So How Is the Illegal War Going?

The Trump administration keeps killing people in the Caribbean in the hopes of... what, exactly?

Nov 16
 
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white sailboat in body of water during sunset
Photo by Knut Troim on Unsplash

Say, remember last week, when I wrote about the oral arguments regarding IEEPA tariffs at the Supreme Court and noted how disturbing it was that a constitutional lawyer would trot out tautologies to justify radical expansions of presidential power? The tautology came from an exchange between two conservative constitutional lawyers — Stanford University’s Michael McConnell and Catholic University’s Chad Squitieri —in Politico:

McConnell: Is there any evidence we have come to a tipping point [that indicates a national emergency]?

Squitieri: Yes, that emergency declaration made by the president of the United States.

McConnell: Is there any evidence that we have come to a tipping point? I’m not asking what the president said.

Squitieri: Yes, a presidential emergency declared by the president of the United States, who was elected by the American people, to make those types of statutory declarations.

The hard-working staff here at Drezner’s World has begun to notice a pattern in which the legal justification for a presidential action rests primarily on Donald Trump’s simply asserting something is true without any factual foundation. In the above example, it was the president declaring a national emergency over trade deficits, when no such emergency exists.

Now it seems that the president is doing this to justify a possible invasion of Venezuela. And I’m worried about where this has gone and will be going.

Drezner’s World is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

The New York Times’ Charlie Savage and Julian Barnes report on a Justice Department memo that sounds awfully flimsy to me:

A secret Justice Department memo blessing President Trump’s boat strikes as lawful hangs on the idea that the United States and its allies are legally in a state of armed conflict with drug cartels, a premise that derives heavily from assertions that the White House itself has put forward, according to people who have read it.

The memo from the department’s Office of Legal Counsel, which is said to be more than 40 pages long, signed off on a military campaign that has now killed 80 people in the Caribbean Sea and eastern Pacific Ocean. It said such extrajudicial killings of people suspected of running drugs were lawful as a matter of Mr. Trump’s wartime powers.

In reaching that conclusion, the memo contradicts a broad range of critics, who have rejected the idea that there is any armed conflict and have accused Mr. Trump of illegally ordering the military to commit murders….

The memo, which was completed in late summer, is said to open with a lengthy recitation of claims submitted by the White House, including that drug cartels are intentionally trying to kill Americans and destabilize the Western Hemisphere. The groups are presented not as unscrupulous businesses trying to profit from drug trafficking, but as terrorists who sell narcotics as a means of financing violence…..

The memo asserts that boats believed to be carrying narcotics are lawful military targets because their cargo would otherwise generate revenue that cartels could use to buy military equipment to wage the purported armed conflict.

And a lengthy section at the end of the memo, they said, offers potential legal defenses if a prosecutor were to charge administration officials or troops for involvement in the killings. Everyone in the chain of command who follows orders that comply with the laws of war has battlefield immunity, the memo says, because it is an armed conflict….

in endorsing Mr. Trump’s determination that there is an armed conflict, the memo accepted the White House’s assertions uncritically, according to the people who have read it.

For example, they said, the memo cites the White House’s claim that cartels are responsible for the deaths of tens of thousands of Americans a year. But it does not address the fact that a surge in overdoses over the past decade was caused by fentanyl, which comes from labs in Mexico controlled by Mexican cartels, not by South American cocaine.

The memo also cites violence by drug cartels against the security forces of other governments in the region, like Colombia’s and Mexico’s, and asserts that the United States can attack the cartels as a matter of collective self-defense, the people who have seen the memo said….

Despite concluding that an armed conflict is underway, the memo also says the operation is not covered by the War Powers Resolution, a 1973 law that requires presidents to terminate deployments of troops into “hostilities” after 60 days if Congress has not authorized them.

It is extremely unusual for a DOJ memo to preemptively declare that members of the armed forces are immune from prosecution. That is the kind of thing that usually does not need to be said. The New Republic’s Greg Sargent also wrote on this oddity:

In other words, administration lawyers appear to be preemptively laying out arguments for why people down the chain of command are acting legally in carrying out these orders. Where does the need for this extra step come from, exactly?….

Representative Adam Smith, ranking Democrat on the House Armed Services Committee, says it’s not typical for such a memo to offer an affirmative legal shield against future prosecution. After all, the memo itself is supposed to explain why the actions are legal, so that line would appear superfluous.

“It is highly unusual to say in it that ‘we’re going to give legal protection for these actions,’” Smith told me.

Smith said this should be read alongside the news, reported by CNN, that the United Kingdom has halted sharing intelligence about suspected drug-trafficking vessels with the U.S. The U.K. does not want to be complicit in unlawful strikes, CNN claims.

“They think that what we’re doing is illegal,” Smith said….

Congress has not authorized these bombings, which have now killed at least 80 people in 20 strikes. So Trump is claiming that he has inherent constitutional authority to order the strikes to defend the country against acts of war. Legal experts point out that this effectively hands Trump the authority to unilaterally execute civilians who are not waging war against the United States in any recognizable sense. And they note that the bombings might be violating other U.S. criminal and international laws….

There’s already plenty of evidence that some of these boats might not even be trafficking drugs to the U.S. in the first place. But now this memo is leading us even deeper into Trump’s hall of mirrors by effectively claiming this evidence exists because the White House says it does. And anyone who is carrying out these orders should rest assured: The orders are legal. After all, the memo says so.

Beyond the Trump administration’s…. let’s say “tortured” relationship with the truth, there are other signs that these airstrikes might not be entirely legal. Last month Admiral Alvin Holsey left his position as head of the U.S. Southern Command after one year of what is ordinarily a three-year tour — reportedly because he raised questions about the legality of these airstrikes. The families of some of the killed fishermen vehemently deny that their relatives were narco-terrorists and have hired U.S. lawyers to sue the federal government. Then there is the fact that the United States Navy rescued survivors of one of the boat strikes — and then decided to repatriate those survivors to their countries of origin. Needless to say, it’s super-weird to simultaneously declare that there is a state of armed conflict while releasing alleged participants of said conflict.

Finally, there is the ultimate question: where is this all headed? So far the United States has killed approximately 80 people over 20 airstrikes. There has been a significant buildup of naval assets in the Caribbean. The obvious but unspoken goal of all this activity is to oust Venezuela’s Nicholas Maduro from power.

And yet, technically, these airstrikes have nothing to do with Venezuela. The NYT’s Barnes and Savage reported that the DOJ memo “does not mention Venezuela.” There has been public reports about the CIA conducting covert operations inside Venezuela — although it’s unclear to what end.

More disturbingly, Politico’s Nahal Toosi reports that the Trump administration: a) does not exactly possess well thought-out plans for how to oust Maduro; and b) does not have great plans on what to do if Maduro is actually ousted:

Some Trump aides are hoping that the threats of U.S. military action alone spur chaos in Maduro’s regime and cause him to lose his grip on power.

The Trump team — fairly or not — isn’t known for its long-term thinking, so it’s notable that aides are pondering post-Maduro scenarios at all. It’s a sign that Trump isn’t about to abandon his campaign in the region (as is Trump’s recent deployment of a massive aircraft carrier there). Which aspects of these plans the U.S. chooses to pursue could offer clues about how much of a role it plays in Venezuela, and the broader region, for years to come….

From what I gathered, the post-Maduro talks in the administration are not robust or well-coordinated. Instead, a few people are thinking through the topic at a range of institutions (State, Energy, Treasury, Justice, Defense, the White House and more). Some are reaching out to former U.S. officials and outside analysts.

The Venezuelan opposition has said it has its own plans for what to do in Venezuela in the immediate hours and days after Maduro’s fall. But while Trump aides are in touch with the opposition, the U.S. official and two of the people told me the administration is not integrating the opposition in any serious way into its ongoing planning.

But we’re still not talking about a comprehensive, vetted Trump day-after plan for Venezuela….

Some former U.S. officials and others who study Venezuela worry the administration is behind in the post-Maduro planning, that various U.S. departments and agencies aren’t really talking to each other, and that not enough civil servants with expertise have been consulted.

It’s possible, after all, that Maduro falls and is replaced by someone more anti-American or more corrupt — even one of his aides who may turn on him. The cartels, other criminal gangs and armed military units in the country could also wreak havoc.

In the end, this business will get out of control and we’ll be lucky to live through it.

Am I missing anything?

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To be fair, I also didn’t think the U.S. would bomb Iran and was proven wrong.

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