WASHINGTON (AP) — Top U.S. military officials are meeting leaders of Caribbean nations this week as the Trump administration has escalated its firepower in the region as part of what it calls a campaign against drug trafficking.
Defense Secretary Pete Hegseth will travel to Santo Domingo, Dominican Republic, and meet Wednesday with the country’s top leaders, including President Luis Abinader, Minister of Defense Lt. Gen. Carlos Antonio Fernández Onofre and other officials, the Pentagon said Tuesday.
The announcement came the same day that Gen. Dan Caine, chairman of the Joint Chiefs of Staff and President Donald Trump’s primary military adviser, met with Trinidad and Tobago Prime Minister Kamla Persad-Bissessar.
They “exchanged views on challenges affecting the Caribbean region, including the destabilizing effects of illicit narcotics, arms, and human trafficking, and transnational criminal organization activities,” according to a summary released by Caine’s office.
The U.S. military has built up its largest presence in the region in generations and has been attacking alleged drug-smuggling boats since early September. To date, the military, under Hegseth’s command, has carried out 21 known strikes on vessels accused of carrying drugs, killing at least 83 people.
The actions are seen by many as a pressure tactic to get Venezuelan President Nicolás Maduro to step down. The visits by Hegseth and Caine this week come as Trump evaluates whether to take military action against Venezuela, which he has not ruled out despite raising the possibility of talks with Maduro, who has been charged with narcoterrorism in the U.S.
The Trump administration added extra pressure by officially designating the Cartel de los Soles, or Cartel of the Suns, as a foreign terrorist organization on Monday, although the entity that the U.S. government alleges is led by Maduro is not a cartel per se.
While a majority of Caribbean leaders have been muted in their response to the strikes on alleged drug boats, urging peace and dialogue, Persad-Bissessar has stood out for her public praise of the deadly attacks.
In early September, she said she had no sympathy for drug traffickers, adding that “the U.S. military should kill them all violently.” Her remarks and support of the strikes have been condemned by some opposition leaders and regional officials.
Amery Browne, Trinidad’s former foreign affairs minister, told the local newspaper Newsday that Persad-Bissessar’s stance is “reckless,” and that she has isolated herself from Caricom, a regional trade bloc.
According to the Pentagon, Hegseth’s trip to the Dominican Republic will aim “to strengthen defense relationships and reaffirm America’s commitment to defend the homeland.”
Meanwhile, Caine also used his time in the region to visit American troops in Puerto Rico and on at least one U.S. Navy ship, thanking service members for their service and sacrifice over the Thanksgiving holiday, the Pentagon said.
Caine and Hegseth also visited the region in September, going to Puerto Rico after ships carrying hundreds of U.S. Marines arrived for what officials said was a training exercise.
Buildup’s background
As of November 26, 2025, the Trump administration has significantly escalated U.S. military presence in the Caribbean, marking the largest naval deployment in the region since the Cuban Missile Crisis.
This includes approximately 15,000 troops, the USS Gerald R. Ford carrier strike group (with over 75 aircraft), at least 13 warships, five support vessels, a nuclear submarine, and advanced assets like F-35 jets and drone interceptors.
The operation, dubbed Southern Spear, is officially framed as counter-narcotics efforts targeting drug trafficking, with over 20 airstrikes on suspected smuggling vessels since August, resulting in significant casualties.
However, it coincides with heightened tensions over Venezuela’s leadership under Nicolás Maduro, whom the U.S. accuses of directing the “Cartel de los Soles” as a narco-terror network.
On November 24, the administration designated this cartel a foreign terrorist organization, enabling broader legal actions against Venezuelan assets.
Military documents reveal plans to sustain this presence through at least 2028, with logistics contracts for food and support indicating a long-term commitment.
Recent high-level visits—Defense Secretary Pete Hegseth to the Dominican Republic on November 26 and Joint Chiefs Chairman Gen. Dan Caine to Trinidad and Tobago and warships to Puerto Rico—aim to bolster alliances and assess readiness.
President Trump has authorized covert CIA operations inside Venezuela, rejected Maduro’s offer for a delayed resignation, and teased further escalations without ruling out invasion, though he has emphasized avoiding full-scale war.
Likely next steps
Based on administration actions, authorized plans, and ongoing negotiations, Trump’s next moves appear focused on a multi-pronged pressure campaign combining covert action, targeted military measures, diplomacy, and economic levers. These are not inevitable but align with reported strategies to weaken Maduro’s regime and curb drug flows. Here’s a breakdown:
- Expansion of Covert Operations: Trump has greenlit CIA-led activities in Venezuela as the “first step” in a new phase of pressure, potentially including sabotage of regime assets or support for opposition forces to lay groundwork for regime change. This could unfold in the coming weeks, with initial focus on disrupting cartel finances and intelligence gathering. reuters.com +1
- Intensified Targeted Strikes: Building on recent airstrikes (which have killed over 80 people on drug boats), the U.S. may authorize attacks on Venezuelan soil or assets linked to the Cartel de los Soles, now classified as terrorists. This includes using robot boats and drones for precision hits, with the flotilla positioned for rapid response. Analysts see this as a low-risk escalation to signal resolve without full invasion. reuters.com +1
- Diplomatic Outreach to Caribbean Allies: Following Hegseth’s and Caine’s visits, expect more summits with nations like the Dominican Republic, Trinidad and Tobago, and Puerto Rico to secure basing rights, intelligence sharing, and joint exercises. This aims to isolate Venezuela regionally and deter Russian or Chinese influence, with potential announcements of aid packages or defense pacts in December. thehill.com +1
- Renewed Back-Channel Negotiations with Ultimatums: Despite rejecting Maduro’s timeline, the White House is pursuing indirect talks in Caracas and Washington. Trump may issue a public ultimatum—e.g., demanding immediate elections or asset seizures—tied to the FTO designation, while dangling sanctions relief as an incentive. Failure could prompt asset freezes on Maduro allies. reuters.com +1
- Additional Sanctions and Economic Measures: Layered on the terrorist label, the administration could target Venezuelan oil exports, banking ties, or elite properties, aiming to starve regime funding. This fits Trump’s first-term playbook and could be announced alongside hostage releases or deportations, as seen earlier in 2025 when Venezuela agreed to repatriate gang members.
- Sustained or Incremental Military Posture: With contracts locking in troops through 2028, rotations of ships and Marines (e.g., the 22nd Marine Expeditionary Unit) will maintain readiness. If tensions spike—such as Venezuelan retaliation—Trump might deploy more assets, like additional carriers, but reports suggest a preference for “maximum pressure” short of boots-on-the-ground invasion. theintercept.com
These steps reflect a strategy of calibrated escalation, prioritizing deniability and alliances over outright conflict, though risks of miscalculation remain high given Venezuela’s alliances and the region’s volatility. Outcomes depend on Maduro’s responses and domestic U.S. politics.
By KONSTANTIN TOROPIN/Associated Press
Associated Press writer Dánica Coto in San Juan, Puerto Rico, contributed to this report. Grok contributed background and analysis of President Trump’s likely next steps.
