Trump signals he wants Cuba resolved before 2029, says a short military move is on the table

What Trump said and the timeline

In a Thursday conversation with conservative radio host Hugh Hewitt, Trump said his administration is watching events in Havana "very closely" and that he wants to "get Cuba done" before 2029. He labeled the island a "failed" state and, per Politico, this is the first time he has attached a timeframe to potential military action aimed at removing Cuban authorities. He added that Secretary of State Marco Rubio "would love to do it" and that he would "certainly consider" a short military operation.

Trump has previously floated a "friendly takeover" of Havana, said the White House could look to Cuba after the Iran war, and asserted he had the ability to do whatever he wished with the country. He also said he thinks he will have the "honor" of "taking Cuba."

Sanctions, the embargo, and conditions on the island

Cuba has endured repeated nationwide power outages in recent months alongside fuel and food shortages. In May, the country's energy chief, Vicente de la O Levy, said that the nation, with a population of about 10 million, had exhausted fuel oil and diesel, calling the situation "extremely tense."

Cuba's Embassy in Washington, D.C., said Thursday that the U.S. blockade cost the country $8 billion from March 2025 through February 2026. The embassy added that the measures "deepen an energy siege that already leaves hospitals without reliable power and families facing blackouts," calling the blockade "collective punishment that hits ordinary people every day." A photograph from March 30, 2026, shows a tank truck moving through Matanzas.

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Treasury actions and the wider response

Earlier this month, the Treasury Department expanded sanctions to include Cuban oil tankers and Cuban shipping companies. It also cautioned that it may take action against any foreign organization or individual conducting business linked to Cuba's marine or maritime sectors, as one element of a drive "to end the Cuban regime's malign activities, both in Cuba and across our hemisphere." In response, Cuba's Embassy said the new steps "deepen an energy siege."

What this means for your portfolio

Exposure to Cuba's energy logistics or to firms dealing in the island's marine or maritime sectors faces headline risk after Treasury's warning. Layer in an ongoing embargo, new sanctions, and Cuba's energy shortfalls, and the policy path points to more constraints on trade and finance linked to the island.

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