What A Day - Trump’s Deadly Attacks in the Caribbean Sea

Episode Date: October 22, 2025

Since the start of September, President Donald Trump has ordered a series of lethal strikes on boats in the Caribbean Sea, killing dozens of people. His administration has justified the attacks by accusing the boats of carrying drugs. But, we’re more than two months in, and we still haven’t seen any substantial evidence that the people killed were involved in trafficking narcotics. Meanwhile, Trump appears to be focused on Venezuelan President Nicolás Maduro, and last week, Trump acknowledged he authorized the CIA to conduct covert operations in Venezuela. So, to talk more about Venezuela and the legality- or lack thereof- of the Trump administration’s ongoing campaign in the Caribbean Sea, we spoke with Tess Bridgeman, co-editor-in-chief of Just Security and Senior Fellow and Visiting Scholar at the Reiss Center on Law and Security at NYU School of Law. She previously served as Special Assistant to the President, Associate Counsel to the President, and Deputy Legal Adviser to the National Security Council (NSC), and at the U.S. State Department in the Office of the Legal Adviser.And in headlines, Vice President JD Vance visits Israel as Hamas continues to return the bodies of hostages, ICE recruits are going up against fitness testing, and the government is as shutdown as ever.Show Notes:Check out Tess's work – justsecurity.org/author/bridgemantess/Call Congress – 202-224-3121Subscribe to the What A Day Newsletter – https://tinyurl.com/3kk4nyz8What A Day – YouTube – https://www.youtube.com/@whatadaypodcastFollow us on Instagram – https://www.instagram.com/crookedmedia/For a transcript of this episode, please visit crooked.com/whataday Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

It's Wednesday, October 22nd. I'm Jane Koston, and this is what a day. The show's sounding warm, well, cool thoughts to users of the eight-sleep pod mattress. See, the eight-sleep pod mattress is a smart bed, which uses Amazon Web Services to control temperature and other settings. And when AWS went down Monday, so did the temperature control settings on the smart mattress, which led to overheating and other seriously annoying problems for people who just wanted to sleep on their mattress like normal people. Many things can and should be smart. You, maybe your phone, and your watch. But I think it's okay if your mattress is dumb.

On today's show, ICE is losing the fight to push-ups. And President Donald Trump channels his inner Regina George by inviting every GOP senator to a White House luncheon except for Kentucky Republican senator and fugly slut Rand Paul. But let's start with a question. Are we going to war with Venezuela? Because after more than two months of strikes on boats off the coast of the South American country that the Trump administration has alleged are involved with cartels and, quote, narco terrorists, I'm not exactly sure. See, Trump keeps saying that this is all about stopping the flow of fentanyl into the United

States. Here's House Speaker Mike Johnson speaking to ABC's Jonathan Carl on this week last Sunday. Don't you have questions for him about what's happening in the United States? Venezuela. We have this buildup around Venezuela. We have the targeting of these boats. I mean, you must at least have questions. The targeting of the boats? You have drug cartels bringing in fentanyl and boatloads of it that would kill potentially hundreds of thousands of Americans. What we're doing is restoring. You have no questions about how they're doing. No, I believe in peace through strength. And here's Eric Trump, who's not actually a part of his dad's administration, but you know, who cares about rules, explaining on Fox News last week that, yes, this is all about stopping fentanyl from entering

the U.S. And now every single time a boat goes out of Venezuela, it's get blown up into a million pieces, Martha. That's exactly what's happening every single day. I personally have four friends that have lost children to fentanyl. But there are actually a few problems with this narrative. First and foremost, we don't actually know if anyone on the seven boats struck by U.S. forces in the Caribbean Sea were involved in drug trafficking or who they even were.

That's the point Kentucky Republican Senator Rand Paul made on Meet the Press last Sunday. You know, when you kill someone, you should know if you're not at war, not in a declared war, you really need to know someone's name, at least. You have to accuse them of something. You have to present evidence. So all these people have been blown up without us knowing their name, without any evidence of a crime. Secondly, Venezuela isn't a source of fentanyl. According to experts consulted by the New York Times, most of the fentanyl used in the United States comes from Mexico, where the drug is made with a source of fentanyl. chemicals from China and other Asian countries. And then there's the fact that while the Trump

administration has said their focus is on stopping drug traffickers, their actions seem way more focused on getting rid of Venezuelan president, Nicholas Maduro. Sounds very regime-changy to me. So to talk more about Venezuela and the legality, or lack of said, of the Trump administration's actions, I spoke to Tess Bridgman. She's the co-editor and chief of just security and visiting scholar at the Rice Center on Law and Security at the NYU School of Law. Tass Bridgman, welcome to what today. Thanks for having me. It's good to be here. Since early September, there have been a series of U.S. strikes on vessels and the Caribbean Sea off the coast of Venezuela, and dozens of people have been killed. I believe that there have been seven strikes, as that we know of.

Right. Just a big proviso here. The Trump administration claims the boats are involved in drug trafficking, and calling the people aboard things like narco-terrorists. Have any of these claims been substantiated? So far as we know, they have not, the administration has not been terribly forthcoming. They say that they have intelligence indicating that there are drug smugglers, which they call narco-terrorists, as you said,

on board these vessels. But even in closed briefings with Congress, what we've heard from members coming out of those briefings is that they're really unsatisfied with the lack of information coming from the administration, about who's on board, what drugs are allegedly on board those vessels, where they left from, where they're heading to. There are huge question marks just around those basic facts for pretty much all of these strikes. And let's say, theoretically, we knew that these were indeed drug traffickers.

What legal jurisdiction does President Trump have to attack votes in the Caribbean Sea anyway? And when is it legal to use this kind of force? Because as far as I know, as of right now, we are not at war with Venezuela. And these are, you know, this is international waters, as far as I know. Yeah, that is the question. So it's very clear that you can only use military force and self-defense when there's been an armed attack or an imminent threat of armed attack that justifies the right of self-defense in response. We haven't had an armed attack here. we are not in an ongoing armed conflict, so there is no justification for the use of military force

against these boats, whether they're in international waters or somewhere else. But the administration also isn't operating in a law enforcement paradigm. They're not using the Coast Guard to get these vessels to stop, to arrest the people on board, to confiscate the drugs. They're not using any legal process at all. So at bottom, what's going on here is the administration is asserting that the president can simply order the military to engage in killings outside of the law. And there's a need for that. It's murder. Something else that struck me over the weekend, Trump announced that two survivors of a recent strike on an alleged drug smuggling vessel were being returned to their respective home

countries, Colombia and Ecuador for prosecution there. Trump, of course, called the survivors' terrorists. But on Monday, authorities in Ecuador released the Ecuadorian survivor because prosecutor said there was no evidence he did anything. What do we know about their survivors, if anything? We don't know much. I think if we do learn more, we're likely to learn that, we're likely to learn information from Ecuadorian or Colombian authorities or civil society or news media there that has access to them and is likely to tell us more. I sure hope Congress is asking the administration and that the media continues to ask the administration what they know. They held these people for, I think, a couple of days in the end, so they ought to know more.

But more importantly, they ought to have known a lot more than what they've said publicly before they tried to kill them. So let's keep in mind that these are two survivors, right, of one of these unlawful strikes on a boat going from where to where, carrying what, right? We just, we need a lot more facts in order to know that. But presumably, if those facts were sufficient to detain them or for a foreign country to prosecute them, the administration is claiming they were sufficient to, in fact, fact, kill them. So they ought to be able to tell us what it is that they're suspected of doing,

who they are, right? Where they were headed. These basic facts are just simply not known right now. This week, Trump has also decided to make enemies with our strongest military ally in South America, Colombia. He slashed aid to the country and called President Gustavo Petro a, quote, a legal drug leader. What sparked this? Yeah, well, Petro has not been mincing words in explaining that these strikes in the Caribbean are not lawful. And he has been making clear that killing outside of armed conflict is not something that the rule of law can abide. He has claimed that one of the victims of one of the earlier strikes was actually a Colombian fisherman and has said essentially the Trump administration

has murdered this Colombian fisherman at sea. Obviously, Trump doesn't like being called out in that way. He and Petro have had beef in the past as well. So it's not, in fact, surprising that Trump would lash out in this way, but it is at odds with our broader strategy for actually combating drug trafficking in the region. If we want to actually make a dent, we have to look at land routes and we have to look at cooperating with the governments in the region, not cutting off aid. That is what, in fact, enables that cooperation. I think that this goes to my overarching concern, which is that I don't think this is really about drugs at all. Trump recently revealed that the CIA is conducting covert missions in Venezuela, you know, the way you tell people what the CIA is doing.

And during his first administration, Trump tried and failed to push Venezuelan President Nicolas Maduro out of power. Trump is still going after Maduro and has doubled the U.S. bounty on his head to $50 million and is basically making all of the sounds you make when you want to do regime shape. Is that what's happening here? Is Trump trying to settle this unfinished business of pushing out a leader he doesn't like? It could be a prelude to regime change. That's obviously yet to be seen. But look, since the beginning of this, there've kind of been two things going on in parallel, and they're related. One is these strikes on individual boats, and they've killed 32 people.

So it's not a small matter. But it's happening alongside this much larger buildup of military assets in the region. Trump and look, also Hegss, Rubio, others in the administration have been using out loud about strikes on land. And they've certainly been making not so veiled threats about Maduro in particular, who's been, of course, someone Rubio has personally wanted to dislodge from power for quite a long time. If they move in that direction, we'll get a whole new level of illegal because they'd also be using force against Venezuela and a whole new level of, I think, disaster and chaos. region. But it's not clear to me which cooler heads are going to prevail if they've been getting away with this in the Caribbean so far. It's why it's incredibly important for people to call this out for what it is and for Congress to really step up and do its job, because if they can do it in the

Caribbean, they may as well do it in Venezuela next. And they might label others terrorists and try to use this same playbook against them. So I think we should keep our eye on what's going on with who the president is labeling as a terrorist and what the limiting principle is. for when he says he can use force against them. His deployments of the military domestically don't give us a lot of comfort that he might not try to use the same playbook here. You talked about Congress,

and we've heard from Kentucky Republican Senator Rand Paul and Virginia Democratic Senator Tim Kaine wanting to rein in these kind of strikes and especially wanting some answers to the questions you and I have just been asking, but do they have the power to check this kind of military action? I mean, there's this joke on blue sky you'll see sometimes

about how, you know, someone will say something about how, like, but I thought dogs couldn't play basketball and the dog is like dribbling around them. And this feels like a moment where you're like, but I thought you had to ask Congress. And meanwhile, we're shelling fishing boats. So what can lawmakers

actually do here? There are a lot of things they can do if they have a little bit of bipartisan unity. And that tends to be the problem here. There's some things they can do even without that. So, first, and foremost, they can pass a resolution saying that the president has to terminate the use of U.S. armed forces in these operations. They tried to do that and failed on what was more or less a

party-line vote, though not completely, earlier this month. And there's likely to be a resolution teed up soon that rather than trying to force the president to withdraw from these particular operations in the Caribbean tries to prevent him from being able to use force inside of Venezuela. So we should keep our eyes on that vote coming up, using the fast-track procedures of the War Powers Resolution. Another thing that's going to be coming up soon, which is also a mechanism of the War Powers Resolution, which is a statute Congress passed back in 1973 to try to rein in a past president, Nixon, and his uses and abuses of the military abroad, is that within 60 days of reporting that first strike, actually just by operation of law without Congress doing anything else,

the president is required to terminate the use of armed forces unless they've been authorized by Congress. So unless we see Congress taking a vote saying, yes, you may start striking whoever is in these vessels. Come around November 4th, the War Powers Resolution 60-day clock is going to run, and Congress needs to insist that that be honored. There's lots they can do in the oversight domain, but they could actually stop these actions with a vote under the War Powers Resolution, or with cutting off the funds for them if they had the votes to do it. Tess, thank you so much for joining me. This has been super informative. Thank you. It was a pleasure to be on. That was my conversation with Tess Bridgman, co-editor-in-chief of Just Security,

and visiting scholar at the Rice Center on Law and Security at the NYU School of Law. We'll link to her work in our show notes. We'll get to more of the news in the moment, but if you like the show, make sure to subscribe, leave a five-star review and up a podcast, watch us on YouTube, and share with your friends. More to come after some ads. What a day is brought to you by ORA frames. Need the perfect gift for literally anyone? Get a digital picture frame from ORA.

I take photos. A lot of photos. And I want to see them. So having an ORA frame has been a godsend. It comes with unlimited storage and simple controls in the frame, so you can upload as many photos as you want, and mom or dad or anyone else can pick the perfect one. See why it was named the number one digital frame by wirecutter,

the strategist, and wired. You can save on the perfect gift that keeps on giving by visitingoraframes.com. For a limited time, listeners can get $20 off their best-selling CarverMet frame with code ora 20. That's A-U-R-A-Frams.com promo code, Aura-20. Support the show by mentioning us at checkout, terms and conditions apply. Here's what else we're following today. Head aligns. The Senator Scholar said he reached out to you about meeting on the government shutdown.

Will you meet with them before you leave for Asia on Friday? Well, I will. Actually, I'd love to meet with them. I just want them to open up the country first. President Trump made his position about ending the shutdown clear to reporters in the Oval Office on Tuesday. Hours before, Trump gathered GOP senators in the Rose Garden for lunch. Every Republican senator received that invite except for one. If everybody were just missing one person, you'll never guess who that is. Let me give you, he automatically votes no and everything. He thinks it's good politics. It's really not.

On the outside looking in was Kentucky Republican Senator Rand Paul, who is, I must admit, pretty good at politics, given that he has been in the Senate since 2011. He has voted against the GOP resolution to fund the government, arguing that it would add too much to the national debt. And in response to his snub, Paul took the age-old approach of pretending he had cooler plans anyway. The senator tweeted out a picture with GOP House member Thomas Massey, another Kentucky Republican who has opposed some of Trump's agenda for being too costly. Also on Tuesday, a group of 13 House Republicans wrote a letter to Speaker Mike Johnson

advocating for the extension of the Affordable Care Act subsidies that Democrats are holding out for during the government shutdown. Their letter makes it clear that they oppose negotiating over health care until the government is reopened, and that, quote, significant reforms are needed to make these credits more fiscally responsible. But at the same time, the letter is a sign of just how much pressure some GOP politicians in competitive districts are feeling during the shutdown. Vice President J.D. Vance arrived in Israel on Tuesday and said that he has, quote, great optimism the ceasefire between Israel and Hamas will hold. That's despite both sides accusing each other of violating the terms of the agreement since it went into effect earlier this

month. On Sunday, Israeli military strikes killed at least 45 people in Gaza, according to health officials there. Israel says it launched those strikes in response to an attack in which Hamas militants killed two Israeli soldiers in southern Gaza. Since the start of the ceasefire, Israel has allowed more aid to go into Gaza, but is still keeping the Rafa border crossing with Egypt closed over accusations that Hamas is delaying the return of bodies of the seized hostages. Hamas returned two more bodies on Tuesday. Speaking at a press conference earlier in the day, flanked by Jared Kushner and Special Envoy to the Middle East, Steve Whitkoff, Vance did call for some patience when it comes to the return of the bodies.

This is difficult. This is not going to happen overnight. Some of these hostages are buried under thousands of pounds of rubble. Some of the hostages, nobody even knows where they are. That doesn't mean we shouldn't work to get them, and that doesn't mean we don't have confidence that we will. It's just a reason to counsel in favor of a little bit of patience. But because patience is not a word Donald Trump understands.

the president posted Tuesday on truth's social that if Hamas does not uphold its end of the ceasefire, quote, an end to Hamas will be fast, furious, and brutal. Now, for some potentially good news for pro-Palestinian activist and recent Columbia University graduate, Mahmoud Halil. On Tuesday, Halil and his lawyers appeared before a federal appeals panel in Pennsylvania to argue that the government tried to unlawfully redetain or deport him after his release from a Louisiana detention center in June. His team says it's in retaliation for Khalil's pro-Palestinian speech during university protests, which is a clear violation of his First Amendment rights. The panel sounded skeptical of the government's case.

Here's Halil speaking outside the federal courthouse. I feel confident, of course, the Trump administration is still trying to redetain me. They're trying to stop, actually, the federal court from looking at my case because they know they don't have a case against me. The Third Circuit said it will need time to deliberate and the judges did not issue a ruling, but it's looking good for Haleel. Unfortunately, that's where the good news ends. Halil still faces separate deportation proceedings in Louisiana, where ICE transferred him after his arrest in New York. Back in April, an immigration judge in Louisiana sided with

ICE, ruling that Haleel could be deported to Syria or Algeria, not for his activism, but over what the government called technical errors on his green card application. Haleel's lawyers have said they intend to appeal the deportation order. Immigration and customs enforcement is facing its toughest battle yet, and no, it's not Portlanders and animal costumes. It's fitness testing. According to a report by the Atlantic, more than a third of ICE recruits at the agency's Training Academy in Georgia have failed the fitness test so far. The test consists of 15 push-ups, 32 sit-ups, and also running 1.5 miles in 14 minutes. Two officials told the Atlantic the

1.5 mile run has toppled more trainees than any other requirement. Am I shocked that the Department of Homeland Security's white nationalist adjacent to join ICE ads haven't been attracting our nation's best? Not really. Department of Homeland Security officials say the failure rate is just a small group of candidates and doesn't reflect the larger pool. Sure. Officials told the Atlantic the slow walking brigade is hindering the agency's plan to hire,

train, and deploy 10,000 deportation officers by January. Whomp, wamp, wamp. The magazine also cited an email from ICE headquarters to the agency's top officials that said, quote, a considerable amount of athletically allergic candidates had been showing up to the academy. One official told the Atlantic, quote, it's pathetic. Checks out. And that's the news. Before we go, the holidays are around the corner and we're excited for gathering, baking, and our favorite tradition, participating in the unhinged discourse about Santa.

Just in time, the crooked store brought back the fan favorite Santa is a woman crewneck sweatshirts and longslave teas, this time in festive new colors. Grab one to wear to your next holiday party or at your family Christmas, both of which were definitely. organized by a woman because a man has never been thoughtful enough to get every sibling the perfect gift, let alone the whole world. Pick one up now at cricket.com slash store. That's all for today. If you like the show, make sure you subscribe, leave a review, wave goodbye to Paul, Nazi streak, and Gracia, then tell your friends to listen.

And if you're into reading. And not just about the racist group texter nominated to run the Office of Special Counsel reportedly withdrawing his nomination, despite what he called on Twitter, quote, overwhelming support. Like me, what a day is also a nightly newsletter. Check it out and subscribe at crooked.com slash subscribe. I'm Jane Koston, and hardest hit by Ingrosia's exit, his mom, who literally banged on Maryland Democratic Representative Jamie Raskin's office door back in June and demanded a meeting to explain how great her son really was. Sad.

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