In less than 48 hours on Wednesday and Thursday, three developments reshaped the U.S. posture towards Venezuelan President Nicolás Maduro. First, news that President Donald Trump authorized the CIA to carry out lethal operations in Venezuela leaked through the New York Times; then, three B-52 bombers conducted air maneuvers near the Venezuelan coast; and finally, Secretary of Defense Pete Hegseth announced that Admiral Alvin Holsey would step down as head of of U.S. Southern Command, which oversees military operations in Central and South America.
Before those events, the Trump administration’s narrative about Venezuela focused almost exclusively on the Tren de Aragua criminal gang and, more recently, on the Venezuelan state’s alleged connection to a massive drug cartel. The mass deportation of Venezuelans has already begun, along with the suspension of Temporary Protected Status (TPS) makes another 300,000 Venezuelans deportable. Meanwhile, U.S. forces have carried out bombings of “fast boats” allegedly transporting drugs to the United States. These efforts to link Venezuela to both immigration chaos and drug smuggling are directly targeted at Maduro. The U.S. has raised to $50 million the amount of an award for information leading to Maduro’s arrest and conviction on drug trafficking charges.
This development, combined with the B-52 flights and Adm. Holsey’s departure, all trace back to one general under Trump’s leadership.
The leak of Trump’s authorization to the CIA has two possible explanations. It could have been an unintended disclosure, reflecting the familiar internal miscommunication and chaos inside the Trump administration. Or it may have been a deliberate leak, part of the administration’s political trolling strategy, aimed at amplifying pressure on Maduro’s inner circle. Either way, it forced Trump to clarify his remarks to the press, in the hours following the leak, that “we are certainly looking at land now because we have the sea very well under control.”
This development, combined with the B-52 flights and Adm. Holsey’s departure, all trace back to one general under Trump’s leadership: Lt. Gen. Dan Caine, chairman of the Joint Chiefs of Staff. Prior to his current position, Caine served as associate director for military affairs at the CIA from November 2021 until his retirement in December 2024. In June of this year, the strikes on three Iranian nuclear facilities using B-2 bombers were ordered by President Trump. Gen. Caine, along with Hegseth, provided public details following that attack. Holsey’s departure leaves Caine (and Hegseth) with even more control over the U.S. military operations toward Venezuela.
Whether these events of the past week are intended to pressure and divide Maduro’s inner circle without committing to open intervention, or to test the ground for a military intervention, is unclear. But one goal seems increasingly clear, an intentional attempt to detain Maduro, which could trigger a “regime change” in Venezuela.
During his presidential transition, Trump tapped longtime adviser Richard Grenell as his envoy for special missions. Grenell held multiple rounds of talks with Maduro’s government that yielded several concrete steps. In May, Venezuela released one U.S. citizen; two months later, El Salvador transferred from its CECOT maximum-security prison to Venezuela over 250 Venezuelan nationals deported by the U.S.; and Venezuela released a further 10 U.S. citizens as well as a number of its own political prisoners. Meanwhile, the Trump administration reinstated limited oil operations for Chevron, allowing it to resume business under strict terms.
If Maduro ever signals willingness to leave power, Grenell would remain a logical intermediary given his prior contacts. But Grenell’s recent efforts to negotiate with Maduro’s circle have largely failed, and he has reportedly been sidelined by Secretary of State Marco Rubio. Neither Grenell nor the CIA, now stripped of much secrecy, seem to have the bandwidth to influence the White House’s evolving strategy.
All scenarios reflect Trump’s preference to position himself as the decider and the central actor. The past week’s developments represents an alignment of Trump with Rubio, Hegseth and Caine.
Venezuela remains a paradox: a country with the largest proven oil reserves in the world and yet one of the deepest humanitarian crises in the hemisphere.
It also intersects with the rise of María Corina Machado, new recipient of the Nobel Peace Prize, as the central figure of democratic resistance in Venezuela. Though the Maduro regime claimed victory in last year’s presidential elections, physical ballot records verified by independent observers showed an overwhelming victory for Machado’s endorsed candidate, Edmundo González Urrutia. After the election, hundreds of thousands of Venezuelans took to the streets demanding that Maduro acknowledge his defeat. Instead, the regime responded with repression: security forces opened fire on demonstrators, and thousands were detained.
Venezuela remains a paradox: a country with the largest proven oil reserves in the world and yet one of the deepest humanitarian crises in the hemisphere. Years of economic collapse, hyperinflation, and mass migration have left the nation hollowed out. In this context, any renewed U.S. pressure inevitably converges with Venezuela’s internal struggle for democratic restoration.
Looking ahead, two variables are crucial. The first is whether the White House truly trusts the Pentagon and the intelligence community to execute any covert or lethal action with zero civilian casualties and minimal other blowback. The second is whether the opposition aligned with Machado can produce a disciplined transition plan that avoids social turmoil and can be rapidly underwritten with U.S. support to stabilize the economy and ease migration pressures. If both of those tracks solidify, events could accelerate quickly, potentially leading to the ouster of Maduro and his regime. If either one falters, though, the risk tilts toward a longer, messier crisis that would further erode U.S. credibility. Either way, like it or not, Donald Trump’s instinct for spectacle and deal-making may soon shape Venezuela’s fate.