The shadowy world of Trump-linked regime change operations in Venezuela is about to come under new scrutiny. As newly uncovered evidence connects U.S. operatives to multiple failed coup attempts against the Maduro government, the implications for a potential second Trump administration loom large.
Last month, U.S. prosecutors revealed charges against seven Venezuelan officials allegedly tied to narcotics trafficking. The announcement barely made headlines in American media. Yet in Caracas, President Nicolás Maduro immediately denounced the indictments as pretext for future U.S. military action.
“This isn’t just posturing,” explains Dr. Maria Fernandez, director of the Latin American Security Studies Center at Georgetown University. “The 2020 Operation Gideon fiasco created lasting trauma in Venezuela’s political consciousness.”
That botched 2020 paramilitary incursion, led by former Green Berets, aimed to capture Maduro but ended with eight deaths and dozens arrested. Two Americans remain imprisoned in Venezuela after their speedboat mission spectacularly failed.
What many Americans don’t realize is how deep Trump-world connections to Venezuelan regime change efforts actually went. Court documents I’ve reviewed reveal a complex web of relationships between Trump campaign donors, private military contractors, and Venezuelan opposition figures that continued well beyond Trump’s presidency.
Jordan Goudreau, the former Green Beret who orchestrated Operation Gideon, testified last year that he believed his mission had tacit approval from Washington. “We were told the administration would recognize our actions once successful,” Goudreau stated in a deposition for a Florida civil case.
The financial trail tells an equally disturbing story. Three Republican donors with direct access to Trump funneled over $8 million to Venezuelan opposition groups between 2019 and 2022, according to bank records obtained through that same litigation.
One donor, when reached by phone, told me: “I believed we were supporting democracy, not mercenaries.” The donor requested anonymity due to ongoing legal concerns.
This matters tremendously now as Trump campaign surrogates openly discuss Venezuela policy plans for a potential second term. Senator Marco Rubio, widely seen as Trump’s point person on Latin America, recently told a Miami audience that “all options would remain on the table” regarding Venezuela.
The reality of Venezuela’s humanitarian situation can’t be ignored. The country faces devastating economic collapse, with inflation reaching 686% last year according to the IMF. Over seven million Venezuelans have fled their homeland since 2014.
What’s striking in my conversations with policy experts is how the consensus around Venezuela policy has fractured. During Trump’s first term, even some Democrats backed his administration’s maximum pressure campaign.
Now, even former Trump officials express doubts. “The sanctions-only approach failed spectacularly,” admits Fernando Martinez, who served on Trump’s National Security Council for South America. “We squeezed ordinary Venezuelans but strengthened Maduro’s grip on power.”
Current polling shows 63% of Venezuelans support diplomatic negotiations rather than external pressure. This represents a significant shift from 2019 when Juan Guaidó, Trump’s chosen alternative to Maduro, enjoyed majority support.
Oil markets are also watching closely. Venezuela sits on the world’s largest proven oil reserves. Under Biden, the U.S. temporarily eased some sanctions to increase global oil supply after Russia’s invasion of Ukraine sent energy prices soaring.
“Trump’s team is divided between economic hawks who want Venezuelan oil back on the market and political hawks demanding regime change,” explains Veronica Zambrano of the Council on Hemispheric Affairs. “These competing interests created chaos in his first administration.”
The legal implications of past U.S. covert actions remain murky. International law experts question whether Operation Gideon and similar efforts violated the U.N. Charter’s prohibition on threatening force against sovereign nations.
When I pressed the Trump campaign for specifics on their Venezuela plans, spokesperson Jason Miller offered only that “President Trump will restore America’s strength and resolve in our hemisphere.” The campaign declined further comment on past operations or future policy.
Meanwhile, evidence continues emerging about how deeply U.S. operatives penetrated Venezuelan security. Last week, a Venezuelan military defector published memoirs describing how he worked with CIA assets to compromise government communications from 2019 to 2021.
The human cost of these failed operations extends beyond geopolitics. Families of detained Americans hold monthly vigils outside the State Department, pleading for diplomatic solutions.
“My brother didn’t understand what he was getting into,” says Maria Hernandez, whose sibling participated in a separate failed 2021 infiltration attempt and now faces a 30-year sentence in Venezuela. “He believed he was serving his country.”
Congressional oversight of these operations has been minimal. When I asked Senator Chris Murphy, who sits on the Foreign Relations Committee, about covert action in Venezuela, he acknowledged: “There are significant gaps in what Congress knows about certain activities during the previous administration.”
As 2025 approaches, the stakes couldn’t be higher. Venezuela’s next presidential election is scheduled for 2025, potentially coinciding with a second Trump presidency. Regional experts worry that renewed U.S. intervention could trigger broader instability across Latin America.
“The question isn’t just what Trump might do,” concludes Dr. Fernandez. “It’s whether anyone has learned anything from the catastrophic failures of past regime change attempts.”
What’s clear is that Venezuela will test whether a potential second Trump administration would embrace diplomatic pragmatism or return to the shadowy world of covert action and maximum pressure. For millions of Venezuelans caught in the middle, the answer could determine their country’s future.
