As Trump Expands Caribbean Strikes on Cartels, Much is Still Unclear

OPINION — “Extraordinarily violent drug trafficking cartels that the United States has designated as terrorist organizations have wrought devastating consequences on American communities for decades, causing the deaths of tens of thousands of United States citizens each year and threatening our national security and foreign policy interests both at home and abroad…In the face of the inability or unwillingness of some states in the region [the Western Hemisphere] to address the continuing threat…we have now reached a critical point where we must meet this threat to our citizens and our most vital national interests with United States military force in self-defense. Accordingly, at my direction, on September 2, 2025, United States forces struck a vessel [a Venezuelan speedboat] at a location beyond the territorial seas of any nation that was assessed to be affiliated with a designated terrorist organization and to be engaged in illicit drug trafficking activities.”

Those are excerpts from a September 4, 2025, letter to Congress from President Trump under the 1973 War Powers Resolution which requires a report within 48 hours after U.S. military forces undertake an action “into the territory, airspace or waters of a foreign nation,” without Congress having previously adopted a declaration of war.

Other requirements of such a letter are the “circumstances necessitating” U.S. armed forces; the “constitutional and legislative authority” for their use, and the “estimated scope and duration of the hostilities.”

I will discuss the first two requirements below, but as to the last, Trump makes clear he sees no end to this self-declared war on drug cartels by saying, “It is not possible at this time to know the full scope and duration of military operations that will be necessary. United States forces remain postured to carry out further operations.”

I should note here that back in January 2024, with the presidential campaign getting underway, The New York Times reported that Trump’s political campaign had released a video titled “President Donald J. Trump Declares War on Cartels,” and Trump promised to “deploy all necessary military assets, including the U.S. Navy” to impose a full naval embargo on the cartels and to “designate the major cartels as Foreign Terrorist Organizations.”

On January 20, 2025, immediately after his inauguration, Trump signed an Executive Order (EO) that created “a process by which certain international cartels [such as Tren de Aragua (TdA) and La Mara Salvatrucha (MS-13)] and other organizations will be designated as Foreign Terrorist Organizations.” The EO said further that TdA and MS-13 “present an unusual and extraordinary threat to the national security, foreign policy, and economy of the United States. I hereby declare a national emergency, under IEEPA [International Emergency Economic Powers Act], to deal with those threats.”

Having taken those actions, Trump expanded his anti-drug cartel war to include last month doubling up to $50 million the reward for information leading to the arrest and/or conviction of Nicolás Maduro for violating U.S. narcotics laws. Maduro, as head of the Cartel of the Suns, was first indicted on federal charges of narco-terrorism and conspiracy to import cocaine in 2020, during former President Trump's first term. The initial reward was $15 million. It was increased to up to $25 million during the last days of the Biden administration when Maduro assumed a third term as Venezuela’s president despite evidence that he had lost the previous presidential election.

At this time, the U.S. does not recognize Maduro as the rightful president of Venezuela.

It is against that background – Trump’s self-declared war against Western Hemisphere drug cartels and Maduro’s running Venezuela – that the U.S. last month began deploying a Navy force to the Caribbean near Venezuela. By early this month it included three Arleigh Burke-class guided-missile destroyers — the USS Sampson, USS Jason Dunham, and USS Gravely — which are designed to counter threats from the air, land, sea and even undersea simultaneously. Both the Sampson and Gravely have a Coast Guard Law Enforcement Detachment to deal with intercepted drug situations, according to Navy releases.

However, by late August, the Pentagon had also deployed an offensive force that appears to have more than halting possible drug shipments in mind.

Arriving in the area was the Iwo Jima Amphibious Ready Group, including the USS Iwo Jima equipped with AV-8B Harrier attack aircraft and the 22nd Marine Expeditionary Unit, with 2,200 Marines. Additionally there were two amphibious transport dock ships, the USS San Antonio and the USS Fort Lauderdale, plus several Navy P-8 surveillance planes and one attack submarine in the region.

The Cipher Brief brings expert-level context to national and global security stories. It’s never been more important to understand what’s happening in the world. Upgrade your access to exclusive content by becoming a subscriber.

It was with that significant Navy force in the area that on September 2, Trump announced on Truth Social: “Earlier this morning, on my Orders, U.S. Military Forces conducted a kinetic strike against positively identified Tren de Aragua Narco terrorists.” Trump said the strike “occurred while the terrorists were at sea in International waters transporting illegal narcotics, heading to the United States. The strike resulted in 11 terrorists killed in action.”

The New York Times reported the next day that “a senior U.S. official said a Special Operations aircraft — either an attack helicopter or an MQ-9 Reaper drone — carried out the attack on Tuesday morning against a four-engine speedboat loaded with drugs.”

At a briefing for congressional staffers September 9, Pentagon officials acknowledged that the boat had turned around after spotting a military aircraft, and the boat was headed back toward shore when it was sunk.

Other than these limited details, and the widely-seen Pentagon black-and-white video, neither the White House nor the Pentagon have released additional details on the event.

Exiled Venezuelan journalists reported that the destroyed boat and eight of its dead occupants were from the small Venezuelan fishing village of San Juan de Unare in a poor and crime-ridden section of Venezuela’s northwestern coast. Three of the dead were allegedly from nearby Guiria.

According to Latin American news reports, more than 20 years ago, San Juan de Unare became a transit point for drugs, and back on September 1, not one but three boats set out headed east for Trinidad and Tobago (T and T) [not to the U.S.], a key Caribbean transit hub for the international drug trade. It was normal for boats from San Juan de Unare to travel in flotillas, with the logic that some will manage to reach their destination. In this case, the boat hit was a faster speedboat, equipped with four engines of 200 horsepower each.

One more thing worth noting from the Latin press is that the normal crew for similar drug boats would have been three or four, and for that reason the additional passengers could have been men who were either escaping the Maduro regime or had found jobs in Trinidad and were on round trip rides.

These are elements to consider as we remember the U.S. military killed all 11 speedboat passengers outright, without the normal at sea stoppage and searching for drugs as usually done in such circumstances.

That was the case last Saturday when Venezuelan government announced on Saturday that a U.S. destroyer [the USS Jason Dunham] intercepted, boarded and occupied a Venezuelan tuna fishing vessel for eight hours in the waters of the South American country's Special Economic Zone on Friday.

There are many issues to be dealt with about the September 2 incident and Caribbean military buildup. Last Wednesday, 25 Democratic Senators sent a letter to President Trump telling him, “Classifying a clear law enforcement mission as counterterrorism does not confer legal authority to target and kill civilians.”

In turn, they asked 10 questions starting with: “Please clarify the legal and substantive basis for targeting and killing civilians suspected of being affiliated with a designated entity. Please also provide a copy of all legal assessments conducted by the White House, Department of Justice, Department of Defense, or any other entity prior to the strike.’

Another question was: “As noted above, in your September 4th War Powers Report to Congress, you note the ‘potential for further such actions.’ However, you do not specify in that report, nor have you specified elsewhere, any legal authority to take military action to target and kill civilians, including those suspected of committing crimes. What is your legal authority to conduct lethal military operations against civilians at sea, within Venezuela or within other Latin American countries?”

The Senators asked for answers by September 17. Let’s see if they get any answers at all.

Need a daily dose of reality on national and global security issues? Subscriber to The Cipher Brief’s Nightcap newsletter, delivering expert insights on today’s events – right to your inbox. Sign up for free today.

Meanwhile, Defense Secretary Pete Hegseth, in a September 10, interview on the USS Iwo Jima with Fox correspondent Rachel Campos-Duffy said, when asked about this U.S. Caribbean buildup, “We’re going to seek peace through strength. We’re going to put America first. It’s our hemisphere. It’s our homeland, but we are not going to sit back and watch the American people be threatened. We are not going to sit back and watch the American people be poisoned. We’re not going to see people be trafficked, see violent groups exist within our country.”

Hegseth then added, “That’s why you see mass deportations. That’s why you’re seeing criminality being locked down. That’s why our border is being locked down. This [the U.S. military force in the Caribbean] is an extension of that. This is an understanding of exactly how America should project power.”

Although Pentagon officials apparently have not yet shared such details on the September 2 strike with Congress, Hegseth claimed to Campos-Duffy, “I watched the strike live. We knew exactly who it was; exactly what they were doing; exactly where they were going; what they were involved in.”

Hegseth’s words do not replace the need for public disclosure of the facts behind such claims, nor does his rhetoric answer the Democratic Senators’ questions about the constitutional and legal justifications for what’s been going on.

This is all the more true with Trump’s announcement on September 15 that the U.S. military struck another boat allegedly carrying drugs from Venezuela. Trump said three people aboard were killed. A video included in Trump’s announcement shows that the boat, which had only two engines, was not moving when it was blown up. This strike further adds to the questions surrounding this issue.

The Cipher Brief is committed to publishing a range of perspectives on national security issues submitted by deeply experienced national security professionals.

Opinions expressed are those of the author and do not represent the views or opinions of The Cipher Brief.

Have a perspective to share based on your experience in the national security field? Send it to Editor@thecipherbrief.com for publication consideration.

Read more expert-driven national security insights, perspective and analysis in The Cipher Brief