Trump signals Cuba could follow Venezuela's diplomatic path, says Havana 'wants to talk very badly'

By Alex Tanzer, 
updated on June 20, 2026

President Donald Trump told Axios in a recent interview that Cuba may be next in line for a diplomatic opening similar to the one his administration has pursued with Venezuela, and that Havana is eager to begin.

"Cuba wants to talk very badly," Trump said, adding that he plans to deploy Secretary of State Marco Rubio to lead any future discussions with the island's government.

The remarks, first reported by Newsmax, amount to the clearest public signal yet that the administration sees Cuba and Venezuela as linked pieces of a broader Western Hemisphere strategy. Trump did not spell out what a Cuba initiative would look like or whether formal talks are imminent. But his language, and his choice of envoy, suggests the White House is at least testing the waters.

Geography, resources, and 'nice shoreline'

Trump drew a sharp geographic distinction between Cuba and other foreign-policy challenges, contrasting the Caribbean with the Middle East.

"These places are close by. Whereas if you look at Iran, that's a very long trip."

He went further, ranking the proximity of the two Latin American nations to the United States. "Venezuela is relatively close and Cuba is a hopscotch," he said.

The president also drew an economic line between the two countries. "Venezuela has oil. Cuba doesn't," he noted. But he found something else to praise about the island. "Cuba has a nice property and they have nice shoreline," Trump said, a remark that will inevitably fuel speculation about future commercial and tourism possibilities.

Trump's broader approach to the Middle East has leaned heavily on pressure and force. His comments suggest the Western Hemisphere may get a different playbook, one built more on proximity, economic leverage, and the prospect of engagement.

Rubio takes the lead

When asked about next steps, Trump pointed directly to his top diplomat. "We're going to have Marco get involved," he said.

That choice carries weight. Rubio, a Cuban American, has spent years as one of Washington's most vocal critics of the Castro regime and its successors. He has consistently advocated maintaining pressure on Havana and Caracas while supporting democratic opposition movements across the region. Naming him as the point man signals the administration does not intend to offer concessions without conditions.

Rubio is described as one of the administration's most influential voices on Latin American policy. His involvement would give any Cuba opening a hawkish anchor, a negotiator unlikely to trade away leverage for goodwill alone.

No direct quotes from Rubio appeared in the interview. His public posture on Cuba has been well established over the course of his Senate career and now his tenure at the State Department.

What 'following Venezuela's path' means, and doesn't

When asked whether Cuba could follow a path similar to Venezuela's under his administration, Trump answered simply: "Possibly. It's possible."

He did not elaborate on what that path entails. The administration's "recent efforts involving Venezuela" were referenced but not detailed. That leaves a significant gap. Does the Venezuela model mean sanctions relief in exchange for political concessions? Energy deals? Migration agreements? The president left the specifics open.

The ambiguity is likely deliberate. Trump has a long track record of floating diplomatic possibilities publicly before committing to a framework, using media interviews as a kind of opening bid. The approach has produced results that surprised even members of his own party on more than one occasion.

What is clear is that the administration views Cuba and Venezuela as part of a single strategic picture rather than isolated cases. That framing matters. It suggests the White House sees Western Hemisphere policy as a theater where it can rack up visible wins, closer to home, with fewer entanglements than the Middle East or the Indo-Pacific.

Cuba's interest, claim or confirmed outreach?

Trump's assertion that Cuba "wants to talk very badly" is, so far, his word alone. No official Cuban outreach to the administration has been publicly confirmed. No diplomatic communiqué, back-channel report, or third-party confirmation accompanied the president's claim.

That does not make it false. But it means the statement sits in the category of a presidential assertion, significant because of who said it, not because independent evidence backs it up. Whether Havana has made quiet overtures through intermediaries or whether Trump is reading signals from the regime's economic desperation remains an open question.

Cuba's economy has been in severe distress for years, battered by the pandemic, energy shortages, and the cumulative weight of decades of sanctions. The island's government has every incentive to seek relief. Whether it is willing to meet American conditions, particularly conditions set by a Rubio-led negotiating team, is another matter entirely.

The administration has shown a willingness to reverse long-standing policy assumptions when it sees strategic advantage, so a genuine shift on Cuba cannot be dismissed out of hand.

The bigger picture

For decades, Cuba policy has been a third rail in American politics, particularly in Florida. The Obama administration's 2014 opening to Havana drew fierce opposition from Cuban American lawmakers and conservative voters who saw it as a gift to a repressive regime without meaningful concessions in return. Trump reversed much of that opening during his first term.

Any new engagement would have to thread a narrow needle: tough enough to satisfy the administration's own base, flexible enough to produce a tangible outcome, and distinct enough from the Obama approach to avoid the political comparison.

Rubio's involvement helps on the first count. His credibility with Cuban American communities and his hawkish record give the administration cover that a different envoy would not. If Rubio blesses a deal, it becomes far harder for critics on the right to call it a giveaway.

The president has also demonstrated a pattern of forging unlikely partnerships when they serve a policy objective, and a Cuba opening, properly structured, could deliver both a foreign-policy headline and economic opportunities for American businesses.

What remains unanswered

The interview left more questions open than it closed. Trump did not specify a timeline, a policy framework, or preconditions. He did not describe what Venezuela-style engagement has produced so far, or what benchmarks Cuba would need to meet. The format of any talks, bilateral, multilateral, back-channel, went unaddressed.

Nor did Trump explain what "nice property" and "nice shoreline" mean in policy terms. The comment could be an offhand observation. It could also hint at commercial development interests that would give American investors a stake in any diplomatic opening.

The administration has made bold personnel and policy moves with little advance warning before. A Cuba initiative could materialize quickly, or it could remain in the realm of presidential musing for months.

For now, the signal is clear even if the details are not: the White House is thinking about Cuba, and it wants Havana, and the rest of the hemisphere, to know it.

Whether anything comes of it depends on whether Cuba's rulers are willing to deal with an administration that will not confuse engagement with appeasement. That is a test Havana has failed before.

About Alex Tanzer

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