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Is Trump and Rubio's "Last Chance" Approach a Turning Point for Cuba's Regime?

Thursday, May 14, 2026 by Bella Nunez

On Wednesday, Secretary of State Marco Rubio expressed his personal belief that altering Cuba's economic trajectory is unfeasible as long as the current leaders remain in power.

Nevertheless, he introduced a phrase that suggests a potential shift in Havana-Washington relations: "a chance should be given." Rubio clarified that he doesn't anticipate a spontaneous change in Cuba.

These remarks were made during an interview with Sean Hannity on Fox News and were also shared through the State Department's official account.

"The economic direction of Cuba can't be changed while the current leadership remains in place. This leadership must change, as they've proven to be incompetent," Rubio stated.

His full statement unveils a nuanced message from Washington: "I hope I'm wrong. Well, a chance should be given, but I don't think it will happen. We can't alter Cuba's direct course while these individuals run the regime."

Rubio's comments came two days after President Donald Trump posted on Truth Social that Cuba is "asking for help" and "we're going to talk," just before his trip to China.

Trump labeled Cuba as a "failed state" that's "only heading in one direction: downward."

This combination of maximum pressure with hints of conditional negotiation characterizes the administration's dual strategy. Since January 2026, Trump has signed two executive orders and over 240 sanctions have been imposed on the Cuban regime.

On May 7, Rubio announced sanctions against GAESA, the military conglomerate controlling between 40% and 70% of Cuba's formal economy, with illicit assets estimated between $18 billion and $20 billion overseas.

The U.S. set June 5 as the deadline for foreign companies to cease operations with sanctioned Cuban entities.

Meanwhile, at least seven tankers have been intercepted in international waters, slashing Cuba's fuel imports by 80% to 90%. The island endures power outages exceeding 20 hours daily in over 55% of its territory.

Behind the Scenes: The Quiet Negotiation Process

In March, Díaz-Canel publicly confirmed that Cuba was negotiating with Washington regarding the energy blockade.

In April, a U.S. delegation traveled to Havana on the first official flight since 2016, though the meetings collapsed due to Cuba's rejection of imposed conditions.

Rubio has maintained his stance from the start: demanding leadership changes, verifiable release of political prisoners, openness to independent media, and an end to the persecution of dissidents.

The lingering question from Wednesday's statement is whether the phrase "a chance should be given" signals a genuine openness or merely diplomatic rhetoric before ramping up pressure.

The answer might emerge before the June 5 deadline imposed by Washington for the world to sever economic ties with the regime.

Understanding the U.S.-Cuba Relations Under Trump and Rubio

What are the main U.S. sanctions against Cuba under the Trump administration?

Since January 2026, the Trump administration has imposed over 240 sanctions against the Cuban regime, including executive orders targeting entities like GAESA, which controls a significant portion of Cuba's economy.

Why does Marco Rubio believe leadership change is necessary in Cuba?

Rubio argues that the current Cuban leaders are incapable of changing the country's economic direction, suggesting that only a leadership change can foster real progress.

What is the significance of the June 5 deadline set by the U.S.?

The deadline demands that foreign companies cease operations with sanctioned Cuban entities, marking a critical juncture for international economic relations with Cuba.

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