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Trump’s Renewed Focus on Venezuela Has a Catch: His Allies’ Past Shadow Diplomacy

As Trump hones in on Venezuela, a little-explored episode of shadow diplomacy during his first term comes back to light.

Donald Trump
Donald Trump has called Venezuela an “enemy” and floated the idea of seeking refuge in the country if he loses the 2024 election. Andrew Harnik/AP

In the span of a few weeks, Donald Trump called Venezuela an “enemy” and Nicolás Maduro a violent dictator, railed against Venezuelan migrants fleeing to the United States and floated the idea of seeking refuge in Venezuela himself if he loses the 2024 election.

Trump’s former national security adviser, John Bolton, says this oscillation is par for the course with the former president, recounting a little-explored episode of shadow diplomacy during Trump’s first term, when the former president’s personal associates undermined what should have been a consistently hard stance against the Venezuelan autocrat.

In 2018, Trump told Bolton to “get it done” and push Maduro out. Months later, the Trump administration also supported a democratic resistance in Venezuela. But behind the scenes, as The Washington Post first reported, Trump’s personal lawyer Rudy Giuliani and ex-con businessman Lev Parnas hooked up with Congressman Pete Sessions and oil billionaire Harry Sargeant III to offer Maduro a “soft landing” during a phone call in September 2018.

Reached on Thursday afternoon, Bolton reiterated his frustration that Maduro ever came close to snagging a sweetheart deal for himself and close associates.

“I was certainly willing to envision him going to Cuba or Russia or Iran or China. But not in this hemisphere outside of Cuba,” Bolton said of the back-channeled efforts to give Maduro a safe haven in the United States. He called the former president’s tendency to rely on allies like Giuliani “damaging.”

“It indicates that the ‘official’ policy is not the president’s policy. These guys are not part of the official decision-making. It’s hard enough to do national security work without being undercut by them,” Bolton said, adding that “one of the causes” of Trump’s lack of resolve on Venezuela was directly due to the fact that “there were a lot of people outside of regular policymaking channels who talked to Trump all the time.”

Parnas spoke to NOTUS about the deal that never came to fruition.

“It was Maduro’s idea, basically,” Parnas said, describing how an American energy executive concocted a plan to give the dictator safe passage to the United States — with help from Giuliani, who kept Trump in the loop as the talks proceeded.

“Trump has no idea about what goes on in the world. He doesn’t listen to his State Department or the people he should be listening to,” Parnas noted.

In the memoir, Parnas describes being approached by Florida billionaire Sargeant III with a plan to ferry Maduro out of the destabilized country — something the mogul wanted to do with the help of Giuliani, who had Trump’s ear.

The book says that during the conversation, Giuliani took a call from Trump and exited the room — later returning to get briefed on how it went and heading to the White House to fill in the president. The deal never went through and faded into the past. Now Trump is trying to play tough.

Trump and Republicans overall have long won over Venezuelans in the United States with their tough talk around Maduro. Trump has injected Venezuela into most of his recent speeches and interviews, using it as a cudgel against the Biden administration and Vice President Kamala Harris’ 2024 presidential campaign.

With Venezuela in turmoil now that Maduro has declared himself the winner of recent elections that were mired in claims of fraud, Trump has continuously blamed Democrats allowing for a mass migration from that nation, suggesting that Joe Biden and Harris are not “strong” enough leaders to exert pressure on the regime.

But his recent complaints about Venezuelan migrants and comments like those he made to Elon Musk suggesting that it would be “safer” to go to Venezuela should he lose the election than stay in the United States are concerning to those in the opposition movement.

“What’s going to end up happening is that he’s going to have every Venezuelan, at least in Florida, voting for Kamala if he keeps going like that,” one source familiar with the Venezuelan opposition’s thinking told NOTUS.

Venezuelan opposition figures don’t look down on Trump’s shadow diplomacy effort to remove Maduro, even if it means giving him a soft landing.

“I have been a victim of human rights violations. I’ve been persecuted, been in hiding, I have lost my freedom twice and now I am exiled,” Freddy Guevara, a Venezuelan opposition official, told NOTUS in an interview conducted in Spanish. “I can tell you that I personally don’t care at all that I get retribution, just as long as they leave and let the [Venezuelan] people live in peace.”

“It must be understood that justice doesn’t always mean imprisonment,” he added.

But this Trump-era side deal might have run interference with his administration’s official policy against Venezuela, which was overseen by Bolton. In his 2020 memoir about his stint at the White House, The Room Where It Happened, Bolton describes his frustration with Trump repeatedly insisting on meeting Maduro face-to-face, calling the Venezuelan autocrat “too tough” to go down, and complaining that “nobody’s ever heard” of “this kid,” opposition leader Juan Guaidó.


Jose Pagliery and Oriana González are reporters at NOTUS.