President Trump told CNN's Dana Bash on Friday that the Cuban Communist government is "on its last legs" and that a deal may be coming.
He said it plainly, without hedging: Cuba wants to negotiate, he's watching the opening develop, and he plans to send Secretary of State Marco Rubio to handle it.
This is not idle talk. Earlier this year, the United States cut off Cuba's access to oil and money flowing in from Venezuela. The island is experiencing fuel shortages, power cuts, and food scarcity. The economic pressure is doing exactly what it was designed to do.
Trump framed the moment with characteristic directness. Speaking to Bash, he said:
"Cuba is gonna fall pretty soon, by the way, unrelated, but Cuba is gonna fall too."
He then connected the diplomatic opening to his own policy decisions, telling Bash:
"They want to make a deal so badly. They want to make a deal, and so I'm going to put [Secretary of State] Marco [Rubio] over there and we'll see how that works out. We're really focused on this one [Iran] right now. We've got plenty of time, but Cuba's ready — after 50 years."
Fifty years. Two generations of Cubans have lived and died under a regime that the American foreign policy establishment repeatedly failed to dislodge, often because it lacked the will, not the tools. The Post reports that Trump is making the case that the will is now present, and the tools are already deployed.
The choice of Marco Rubio is not incidental. Rubio's parents fled Cuba. He has spent his entire political career calling for the end of the Castro regime. If any American official carries the moral weight and personal stakes to negotiate Cuba's transition, it is him.
Trump made a point of praising Rubio directly during the interview, telling him, "You've been doing a fantastic job on a place called Cuba." That's not throwaway flattery. It signals that Rubio has been actively engaged on Cuba policy behind the scenes, and that Trump is preparing to move him into a more visible role when the moment is right.
Trump also flagged the sequencing clearly. Iran comes first. Cuba follows. The administration is managing multiple pressure campaigns simultaneously and choosing the order of engagement deliberately.
On Thursday, Trump hosted Inter Miami CF, the 2025 Major League Soccer champions, at the White House and raised Cuba multiple times. Then on Friday he repeated and expanded on those remarks in the CNN interview. This isn't a slip of the tongue or an off-the-cuff observation. He is signaling something.
Trump's own account of how the opening developed is candid:
"I've been watching it for 50 years, and it's fallen right into my lap — because of me, it's fallen — but it's nevertheless fallen right into the lap. And we're doing very well."
The policy mechanics bear that out. Cutting off Venezuela's oil subsidies to Cuba was a targeted economic move that removed the lifeline propping up a regime that cannot feed or power its own country. The Cuban government is not negotiating from strength. It is negotiating because it has run out of options.
Trump gave Cuban exiles and their families a direct message, telling Bash it would be "just a question of time" before many of them go back to Cuba, "hopefully not to stay." That line will resonate in Miami in ways that no foreign policy white paper ever could. It is a promise, not a platitude.
The left spent decades insisting that engagement without preconditions was the path to liberalizing Cuba. The Obama administration tried exactly that, and the regime pocketed the concessions without loosening its grip on a single dissident. Pressure, isolation, and economic strangulation are producing what diplomatic goodwill never could.
A Communist government that has brutalized its people for more than half a century is now signaling it wants to make a deal. The man sending Marco Rubio to the table is not interested in giving them an easy exit. Let that sink in.