CHAIRMAN OF THE JOINT CHIEFS MAKES HIS SECOND VISIT TO PUERTO RICO SINCE DRUG STRIKES BEGAN

As operations continue and the number of ships and personnel in the region increases, more and more of the US military is focused on the Caribbean. So, it’s no wonder that America’s top military officer made a trip to Puerto Rico to tour the recently reopened Naval Station there and speak to the troops stationed on the island and deployed aboard ships nearby. On Monday, November 24th, Chairman of the Joint Chiefs of Staff General Dan Caine visited the US forces conducting anti-drug operations in the Caribbean Sea. Men and women who may soon find themselves involved in strikes against Venezuela.

What is the Military Situation in the Caribbean?

The US military’s focus on operations in the Caribbean Sea and related to several South American countries that border it began at the start of September 2025 with the first airstrike on an alleged drug boat, footage of which President Donald Trump made public on the 2nd of that month. Since then, the military has sunk over 20 more alleged drug-carrying vessels in the Caribbean as well as the Pacific Ocean, killing at least 80 people.

Starting on November 13th, these strikes began falling under Operation Southern Spear. And three days after that, the USS Gerald Ford, the largest and most advanced aircraft carrier in the world, entered the Caribbean along with the rest of her strike group. They joined the Sailors and Marines of the 22nd Marine Expeditionary Unit, who’d been in the region since shortly after the strikes began, bringing the total number of American Armed Forces personnel in Puerto Rico and the waters around it to roughly 15,000.

While those are the basic facts of the situation, there have also been multiple hiccups and controversies during the operation. Numerous legal and military experts have questioned whether the lethal attacks of supposed drug boats are legal under US or international law. In mid-October, Admiral Alvin Holsey, the head of US Southern Command (SOUTHCOM), the combatant command overseeing the strikes, unexpectedly stepped down and announced he’d retire in December. While the actual offensive operations have only targeted alleged narco-vessels at sea, the Trump administration has hinted at the possibility of striking targets within Venezuela and is believed to have already authorized the Central Intelligence Agency to conduct covert operations in the country.

They recently went so far as to designate the Cartel de los Soles, a narcotics syndicate it claims is run by the Venezuelan military and its (possibly illegitimate after their last election) President Nicolas Maduro, as a terrorist organization. Though that is a controversial move in and of itself, “Cartel de los Soles” is more like a bit of local slang used to refer to the rampant corruption in Venezuela than an actual organized cartel.

Reopening of Naval Station Roosevelt Roads

Amid the expanding operations and the rumors of potential attacks against a sovereign nation, and in addition to the deployment of thousands of ship-borne troops to the Caribbean, the Trump administration reopened Naval Station Roosevelt Roads.

Originally commissioned in 1943, the base closed in 2004 but is now returning to active use a mere 21 years later. It is now one of five installations on the island housing American troops and aircraft.

With its extensive airfield that includes a primary runway over 11,000 feet long, the reopened Roosevelt Roads will greatly increase the US military’s ability to rapidly launch aircraft in the Caribbean.

General Caine’s Visit to Puerto Rico

Accompanied by his senior enlisted advisor, Navy SEAL and Master Chief Petty Officer David Isom, General Caine flew to Puerto Rico on Monday to visit troops stationed and/or deployed there. His presence will likely strike Maduro and the Venezuelan government as further evidence of the seriousness of the Trump administration’s military focus on the Caribbean.

Though the official stated reason for their visit is to “engage with service members and thank them for their outstanding support to regional missions.” What those “regional missions” could include in the coming days, weeks, and months remains to be seen.

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