Trump Draws Red Line: Cuba Faces Oil Blockade After Venezuela Topples

Paul Riverbank, 1/24/2026The U.S. ousted Venezuela's Maduro and now eyes Cuba, signaling a forceful return to interventionist policy in Latin America. With economic blockades and military pressure, Washington is making clear—this new era will be shaped by action, not just rhetoric.

During the Trump administration, foreign policy in the Western Hemisphere stopped dancing around the edges. The language of “restoring American preeminence” and references to the Monroe Doctrine weren’t rhetorical flourishes—they were groundwork laid out in briefing rooms and echoed in interviews. When action landed, it was swift. Maduro’s regime, long propped up by loyalists and protected by secrecy, ultimately fell because someone close to him—an aide turned informant, by all credible accounts—passed along the kind of granular details intelligence agencies can use: travel routines, hiding spots, even safehouse addresses. Few insiders could have anticipated how quickly those breadcrumbs were trailed.

Maduro disappeared from the scene, and his vice president, Delcy Rodríguez, stepped in with a noticeably different tone. There were whispers—originating both in Washington and Caracas—that Rodríguez had, in the weeks before the intervention, floated private overtures to U.S. officials, hinting at a willingness to broker a deal. Nothing concrete solidified, but the approach marked a sharp break from the pugnacious stance of the previous administration.

Meanwhile, the playbook for Cuba appears to be evolving in plain sight. In recent weeks, U.S. officials have discreetly solicited information from Cuban exile groups in Miami and beyond, quietly assembling lists of government insiders who might be swayed by promises of reform or guarantees of safety. The outreach recalls Cold War intelligence-gathering, but the stakes are uniquely modern: smartphones, sanctions, and a world economy already battered by uncertainty.

Senator Marco Rubio, now Secretary of State, cut through diplomatic niceties in a press conference as he described Cuba’s current state—recalling his own family’s escape, but offering little nostalgia. “It’s a failing nation right now,” he told reporters, his South Florida Spanish inflection barely softened by years in Washington. “If I lived in Havana and had even a minor role in government, I’d be worried this month, not next year.”

Behind the scenes, policymakers know time is not on Havana’s side. Cuba’s years-long dependence on Venezuelan oil—once accounting for roughly 70% of its energy needs—has become a brittle lifeline. With Caracas unable to honor old deliveries, blackouts have become a daily reality in cities that rarely needed candlelight except for romance or hurricane drills. Cuban economist Pavel Vidal, who has tracked the island’s economic pulse for years, offered a blunt assessment: “If oil shipments actually stop, the Cuban economy simply stops too.”

The administration’s toolkit isn’t limited to rhetoric or clandestine diplomacy. Senior officials have confirmed ongoing discussions about leveraging a full blockade on Cuba’s oil imports, hoping to force the regime’s hand without firing a shot. “No final decisions,” a senior advisor told me, “but there’s strong backing—Rubio is only the most vocal.” The message was clear enough, though the implications for ordinary Cubans remain deeply uncertain.

President Trump, never one for subtlety, hammered the point home on social media: “THERE WILL BE NO MORE OIL OR MONEY GOING TO CUBA — ZERO! I strongly suggest they make a deal, BEFORE IT IS TOO LATE.” The post drew both condemnation and quiet praise, depending on which hemisphere you were standing in. But the impact was immediate; energy rationing intensified, and whispers of discontent grew amongst Havana’s party faithful.

Complicating matters, U.S. naval assets have shifted position again. Months after deploying the USS Abraham Lincoln to project power near Iran, carriers were seen off the Caribbean, not idling but visible. It’s an unsubtle reminder for the Cuban military—the balance of force has already changed in Venezuela, and the Caribbean is well within arm’s reach.

For Washington’s strategic thinkers, this isn’t just about ideology. Senior officials frame the stakes in terms of national security—no tolerance for foreign military bases on Cuban soil, no appetite for intelligence operations run by external powers within striking distance of the American mainland. “Illegitimate regime,” Rubio has called the current government more than once, suggesting that the next chapter is already being drafted—if not by Cubans themselves, then certainly with their awareness.

Events in the Western Hemisphere rarely unfold on anyone’s preferred timetable. But with Venezuela’s government toppled, pressure on Havana reaching new levels, and diplomats as well as exiles being pressed into service, a familiar but rarely straightforward American doctrine has resurfaced: speak less, act more, and let the results write the headlines.

If the past few months are any guide, this will be a season for surprise announcements and uneasy deals. For now, the only certainty is that the center of gravity in Latin America is shifting, and the world is watching the next domino closely.

Not so long ago, few would have predicted the United States would intervene directly in Venezuela’s political crisis, but this year Washington made an audacious move—ousting Nicolás Maduro. In Caracas, the abrupt shift left allies and detractors reeling, while the reverberations have been felt as far as Havana. As speculation mounts over where the White House might turn its gaze next, many are watching Cuba with renewed intensity, sensing familiar patterns amid fresh uncertainty.During the Trump administration, foreign policy in the Western Hemisphere stopped dancing around the edges. The language of “restoring American preeminence” and references to the Monroe Doctrine weren’t rhetorical flourishes—they were groundwork laid out in briefing rooms and echoed in interviews. When action landed, it was swift. Maduro’s regime, long propped up by loyalists and protected by secrecy, ultimately fell because someone close to him—an aide turned informant, by all credible accounts—passed along the kind of granular details intelligence agencies can use: travel routines, hiding spots, even safehouse addresses. Few insiders could have anticipated how quickly those breadcrumbs were trailed.Maduro disappeared from the scene, and his vice president, Delcy Rodríguez, stepped in with a noticeably different tone. There were whispers—originating both in Washington and Caracas—that Rodríguez had, in the weeks before the intervention, floated private overtures to U.S. officials, hinting at a willingness to broker a deal. Nothing concrete solidified, but the approach marked a sharp break from the pugnacious stance of the previous administration.Meanwhile, the playbook for Cuba appears to be evolving in plain sight. In recent weeks, U.S. officials have discreetly solicited information from Cuban exile groups in Miami and beyond, quietly assembling lists of government insiders who might be swayed by promises of reform or guarantees of safety. The outreach recalls Cold War intelligence-gathering, but the stakes are uniquely modern: smartphones, sanctions, and a world economy already battered by uncertainty.Senator Marco Rubio, now Secretary of State, cut through diplomatic niceties in a press conference as he described Cuba’s current state—recalling his own family’s escape, but offering little nostalgia. “It’s a failing nation right now,” he told reporters, his South Florida Spanish inflection barely softened by years in Washington. “If I lived in Havana and had even a minor role in government, I’d be worried this month, not next year.”Behind the scenes, policymakers know time is not on Havana’s side. Cuba’s years-long dependence on Venezuelan oil—once accounting for roughly 70% of its energy needs—has become a brittle lifeline. With Caracas unable to honor old deliveries, blackouts have become a daily reality in cities that rarely needed candlelight except for romance or hurricane drills. Cuban economist Pavel Vidal, who has tracked the island’s economic pulse for years, offered a blunt assessment: “If oil shipments actually stop, the Cuban economy simply stops too.”The administration’s toolkit isn’t limited to rhetoric or clandestine diplomacy. Senior officials have confirmed ongoing discussions about leveraging a full blockade on Cuba’s oil imports, hoping to force the regime’s hand without firing a shot. “No final decisions,” a senior advisor told me, “but there’s strong backing—Rubio is only the most vocal.” The message was clear enough, though the implications for ordinary Cubans remain deeply uncertain.President Trump, never one for subtlety, hammered the point home on social media: “THERE WILL BE NO MORE OIL OR MONEY GOING TO CUBA — ZERO! I strongly suggest they make a deal, BEFORE IT IS TOO LATE.” The post drew both condemnation and quiet praise, depending on which hemisphere you were standing in. But the impact was immediate; energy rationing intensified, and whispers of discontent grew amongst Havana’s party faithful.Complicating matters, U.S. naval assets have shifted position again. Months after deploying the USS Abraham Lincoln to project power near Iran, carriers were seen off the Caribbean, not idling but visible. It’s an unsubtle reminder for the Cuban military—the balance of force has already changed in Venezuela, and the Caribbean is well within arm’s reach.For Washington’s strategic thinkers, this isn’t just about ideology. Senior officials frame the stakes in terms of national security—no tolerance for foreign military bases on Cuban soil, no appetite for intelligence operations run by external powers within striking distance of the American mainland. “Illegitimate regime,” Rubio has called the current government more than once, suggesting that the next chapter is already being drafted—if not by Cubans themselves, then certainly with their awareness.Events in the Western Hemisphere rarely unfold on anyone’s preferred timetable. But with Venezuela’s government toppled, pressure on Havana reaching new levels, and diplomats as well as exiles being pressed into service, a familiar but rarely straightforward American doctrine has resurfaced: speak less, act more, and let the results write the headlines.If the past few months are any guide, this will be a season for surprise announcements and uneasy deals. For now, the only certainty is that the center of gravity in Latin America is shifting, and the world is watching the next domino closely.