Trump’s Bold Gamble: Flights Resume, U.S. Grips Venezuela’s Oil Revenue

Paul Riverbank, 1/30/2026 U.S.-Venezuela relations thaw as Trump lifts travel bans, airlines plan returns, and oil sales face tight oversight. Diplomatic and commercial ties stir hope for recovery, though sharp security warnings and unresolved risks remind us that Venezuela’s path forward remains fragile and closely watched.

Almost as if their phones had rung at the same moment, a handful of nervous airline executives started sharing news of their own. American Airlines, which once flew to Venezuela long enough to know the rhythm of its airports and the airport workers by name, is now hustling to get planes back in the air. “We have a more than 30-year history connecting Venezolanos to the U.S.,” their chief commercial officer, Nat Pieper, said in a statement peppered with optimism. There was talk of families reuniting and the hum of commerce—practical, hopeful, a world away from the atmosphere that drove the carriers out in the first place.

Back in 2019, the situation had felt simpler in its bleakness. Airline giants quietly pulled their crews out months before an official shutdown, spooked by stories—sometimes only half-confirmed—of unrest and trouble for outsiders. When Homeland Security finally slammed the door on all airspace between the two countries, it didn’t seem like it would open again quickly. Tensions with Nicolás Maduro’s government reached their breaking point; embassies locked their doors and politicians swapped accusations on international news. Even now, the State Department’s advisory page still flashes a red “Do not travel” warning in stark terms—crime, instability, real danger. For all the President’s buoyant talk, those words haven’t changed, and the agency hasn't addressed any plans to rewrite them.

Yet, in just the last week, the mood inside the Beltway has subtly shifted. Congressional aides began circulating a letter about the phased return of embassy staff to Caracas. The memo was practical, bureaucratic; it suggested “select” teams would assess conditions and handle limited duties—nobody is talking about business as usual, at least not yet.

Then there’s the oil question, never far from the headlines when it comes to Venezuela. With Nicolás Maduro forced out by a U.S.-led military campaign (itself the largest shift in regional politics for years), Secretary of State Marco Rubio laid out a system as meticulous as it is interventionist. Venezuela could resume oil exports, but under new, tight rules. The cash for any oil sold would go straight into an account under U.S. oversight—a compromise meant to keep Venezuela’s rickety government afloat, but avoid the old patterns of money slipping quietly into the wrong hands. “It’s an account that belongs to Venezuela,” Rubio clarified, “but it has U.S. sanctions as a blocking mechanism.” Routine, maybe, but the kind of routine that gets dissected in hearing rooms.

Senator Chris Murphy barely let the ink dry before questioning the entire scheme. “This sounds like taking their oil at gunpoint,” he argued one morning, demanding proof the set-up wouldn’t just become another lever for foreign interests. Rubio, almost weary, reached for familiar lines about past corruption and countries snapping up fuel at cut rates—a veiled reference to China—insisting the new flow of money ought to mean lights for hospitals and repairs for Venezuela’s battered infrastructure.

Still, real holes remain. In Venezuela’s parliament, debates over how to attract private investment to resurrect the energy sector tend to turn into marathons. Doctors and patients from Caracas to Maracaibo know the shortages firsthand, having bought their own gauze or painkillers—some wounds are far bigger than a single agreement can patch.

Even as embassies prepare to send advance teams scouting for safe places to stay, and airlines redraw their timetables, old anxieties echo. One midweek, a relative of mine in Miami called her brother in Valencia; word of the first direct flights sent their conversation in hopeful directions, but neither was ready to book a ticket just yet.

The White House, true to its message, is gambling that the U.S. can pressure and pilot Venezuela out of its rut. Where repeated warnings and near-total isolation closed off channels, the hope now is that reopening them—slowly, with conditions and oversight—might bring some relief.

Unanswered questions remain stubbornly at the margins of these plans: safety for foreign visitors, success of budget monitoring, whether Venezuela’s chaos is truly behind it. For all the sweeping statements from Washington and proclamations of change, daily life in Venezuela will likely shape the story more than any White House address.

But with reopenings already underway, new embassies being staffed, and oil exports inching forward under close watch, one thing is certain—the conversation has shifted, and for the first time in a while, so has the direction of travel.

It was a scene few expected so soon: cameras snapping as President Trump stepped to the White House podium, waving away five years of warnings with a short, direct announcement: “American citizens will be very shortly able to go to Venezuela, and they’ll be safe there.” Hard to believe, for anyone who remembers headlines just last year, when travelers were being cautioned to stay away at all costs.Almost as if their phones had rung at the same moment, a handful of nervous airline executives started sharing news of their own. American Airlines, which once flew to Venezuela long enough to know the rhythm of its airports and the airport workers by name, is now hustling to get planes back in the air. “We have a more than 30-year history connecting Venezolanos to the U.S.,” their chief commercial officer, Nat Pieper, said in a statement peppered with optimism. There was talk of families reuniting and the hum of commerce—practical, hopeful, a world away from the atmosphere that drove the carriers out in the first place.Back in 2019, the situation had felt simpler in its bleakness. Airline giants quietly pulled their crews out months before an official shutdown, spooked by stories—sometimes only half-confirmed—of unrest and trouble for outsiders. When Homeland Security finally slammed the door on all airspace between the two countries, it didn’t seem like it would open again quickly. Tensions with Nicolás Maduro’s government reached their breaking point; embassies locked their doors and politicians swapped accusations on international news. Even now, the State Department’s advisory page still flashes a red “Do not travel” warning in stark terms—crime, instability, real danger. For all the President’s buoyant talk, those words haven’t changed, and the agency hasn't addressed any plans to rewrite them.Yet, in just the last week, the mood inside the Beltway has subtly shifted. Congressional aides began circulating a letter about the phased return of embassy staff to Caracas. The memo was practical, bureaucratic; it suggested “select” teams would assess conditions and handle limited duties—nobody is talking about business as usual, at least not yet.Then there’s the oil question, never far from the headlines when it comes to Venezuela. With Nicolás Maduro forced out by a U.S.-led military campaign (itself the largest shift in regional politics for years), Secretary of State Marco Rubio laid out a system as meticulous as it is interventionist. Venezuela could resume oil exports, but under new, tight rules. The cash for any oil sold would go straight into an account under U.S. oversight—a compromise meant to keep Venezuela’s rickety government afloat, but avoid the old patterns of money slipping quietly into the wrong hands. “It’s an account that belongs to Venezuela,” Rubio clarified, “but it has U.S. sanctions as a blocking mechanism.” Routine, maybe, but the kind of routine that gets dissected in hearing rooms.Senator Chris Murphy barely let the ink dry before questioning the entire scheme. “This sounds like taking their oil at gunpoint,” he argued one morning, demanding proof the set-up wouldn’t just become another lever for foreign interests. Rubio, almost weary, reached for familiar lines about past corruption and countries snapping up fuel at cut rates—a veiled reference to China—insisting the new flow of money ought to mean lights for hospitals and repairs for Venezuela’s battered infrastructure.Still, real holes remain. In Venezuela’s parliament, debates over how to attract private investment to resurrect the energy sector tend to turn into marathons. Doctors and patients from Caracas to Maracaibo know the shortages firsthand, having bought their own gauze or painkillers—some wounds are far bigger than a single agreement can patch.Even as embassies prepare to send advance teams scouting for safe places to stay, and airlines redraw their timetables, old anxieties echo. One midweek, a relative of mine in Miami called her brother in Valencia; word of the first direct flights sent their conversation in hopeful directions, but neither was ready to book a ticket just yet.The White House, true to its message, is gambling that the U.S. can pressure and pilot Venezuela out of its rut. Where repeated warnings and near-total isolation closed off channels, the hope now is that reopening them—slowly, with conditions and oversight—might bring some relief.Unanswered questions remain stubbornly at the margins of these plans: safety for foreign visitors, success of budget monitoring, whether Venezuela’s chaos is truly behind it. For all the sweeping statements from Washington and proclamations of change, daily life in Venezuela will likely shape the story more than any White House address.But with reopenings already underway, new embassies being staffed, and oil exports inching forward under close watch, one thing is certain—the conversation has shifted, and for the first time in a while, so has the direction of travel.