By Vera Bergengruen, Juan Forero, Alex Leary and Kejal Vyas
Six months before he sent U.S. forces to seize Venezuelan President Nicolás Maduro, President Trump wanted to cut a deal with Maduro, not forcibly remove him from power.
During a July meeting in the Oval Office, Trump told advisers that he wanted to keep negotiating with Maduro's regime to reach a deal to give priority to U.S. oil companies seeking to pump Venezuelan crude -- opting for diplomacy with the autocratic leader.
Trump acknowledged that Secretary of State Marco Rubio, who had long cautioned him against trusting Maduro and believed oil revenues would bolster his regime, opposed the approach. But Trump, according to people briefed on the discussion, said he wanted a deal: "We're doing it my way."
In late December, the president decided in favor of military action, fed up with repeated efforts to persuade Maduro to leave office in exchange for amnesty for his alleged crimes. The brazen overnight operation that on Saturday ended with Maduro in a jail in New York offered a test case for a more muscular foreign policy that Trump has signaled he may seek to deploy in other parts of the world, from Colombia to Greenland.
In Trump's second term, Venezuela quickly became an unlikely convergence point for his priorities -- mass deportations, drug trafficking, the lure of the country's vast oil and mineral reserves, and a longstanding push by Rubio, the son of Cuban immigrants, and other hard-liners to depose its brutal regime.
"Venezuela is a perfect storm, it's everything the Trump administration is concerned about," said Elliott Abrams, who handled Venezuelan affairs in Trump's first term.
Trump's fixation on the country's resources, expressed to allies after he took office for the second time, triggered behind-the-scenes jockeying among his advisers and oil lobbyists over the shape of his Venezuela policy. Trump made it clear he cared more about a bargain from Caracas that served his America First agenda, including cooperation on deportations and favorable oil deals, than pressing for a democratic transition.
Ultimately, Rubio and Trump's other hawkish advisers came out on top after they convinced the president that Maduro was a drug-trafficking terrorist who wouldn't leave power on his own.
For his part, Maduro saw Trump's pressure campaign as a bluff, according to former aides and businessmen close to the regime. "President Donald Trump, you must be careful because Marco Rubio wants to stain your hands with blood," he said in September, denouncing U.S. pressure as an attempt to seize the country's resources
Maduro appeared in videos dancing and singing at holiday events, while telling Americans -- in broken English -- that he wanted peace and "don't worry, be happy." Trump privately expressed frustration about the videos, telling aides he believed Maduro was unserious, a senior administration official said.
On Dec. 23, Maduro rejected what he didn't know would be his final offer to leave office. Instead of living out the rest of his days in exile with his family, a helicopter lifted him and his wife out of Caracas and into U.S. custody.
Trump -- for now -- has cautiously embraced the Venezuelan leader's second-in-command, Delcy Rodríguez, after advisers told him the ambitious 56-year-old socialist might be more open to working with U.S. companies.
When Trump returned to the White House last January, he felt he had put too much time and political capital into trying -- and failing -- to oust Maduro in his first term, according to former officials.
But the issue quickly re-entered his orbit. Many of Trump's top allies saw Maduro's clinging to power as a lingering humiliation, and a sign that Washington was tolerating an openly hostile regime in its own hemisphere, former U.S. officials said.
A transactional president who had never warmed up to the Venezuelan opposition, Trump put one of his most trusted aides on thorny international issues, Richard Grenell, in charge.
The directions were straightforward: win the release of American hostages held by Venezuela's regime, secure openings for American oil companies, and persuade Maduro to accept planeloads of Venezuelan migrants the Trump administration wanted to deport. Maduro had stopped accepting deportation flights in early 2024 as talks with the Biden administration broke down.
It seemed to work. Just 11 days into Trump's term, Grenell flew to Caracas and posted photos shaking hands with Maduro at the Miraflores presidential palace. That same day, he returned with six Americans the U.S. said had been wrongfully detained. Deportation flights started back up, regularly departing from the U.S. to Caracas every Wednesday and Friday.
By late December, more than 13,600 Venezuelans had been returned to the country, according to an analysis by ICE Flight Monitor, a group that tracks deportation flights. The deportations were touted in flashy videos by the White House, which contended it was deporting gang members and criminals.
In its first months, the Trump administration continued to promote a hard line on Venezuela in public. Mauricio Claver-Carone, Trump's then-envoy for Latin America, insisted that there was no "quid pro quo" with Maduro.
"It's not a negotiation in exchange for anything," he told reporters last January. "We don't need Venezuelan oil."
Rubio warned the president that the Venezuelan leader had made five deals with different administrations over the past 10 years and had broken all of them, according to a Rubio aide.
Trump decided to offer Maduro a way out.
In May, the U.S. offered Maduro a deal to leave Venezuela for a life in exile in exchange for an amnesty that would shield him from drug charges, according to people familiar with the matter. The sanctions against him and some other regime officials would be lifted and the U.S. in turn would work with a transition government, the people said. One of the people said that there were early discussions about the government being led by Vice President Rodríguez.
The strongman rejected that offer, as well as similar ones that followed.
As U.S. officials juggled priorities on Venezuela, oil remained front and center. Energy companies were pushing hard to convince the government to ease off on sanctions, which they said were excluding Americans from lucrative oil deals and recouping billions of dollars in debts while giving China a stronger foothold in the hemisphere and stoking outward migration from an economically crippled Venezuela.
In July, Chevron regained the ability to pump oil in Venezuela, reversing a move earlier that year to rescind a Biden-era license.
Oil industry lobbyists were fighting for more companies to return to the country. They told Trump administration officials that the regime in Caracas was so desperate that they would welcome U.S. firms with tantalizing terms not seen by the industry in decades -- including no-bid contracts and little environmental or regulatory oversight. But U.S. officials were wary that striking business deals while allowing Maduro to stay in power would anger elements of the president's political base who wanted the Venezuelan leader ousted, according to people familiar with the administration's thinking.
Some top officials, including Rubio and Miller, stressed to Trump that U.S. prosecutors had charged Maduro with being the head of a drug-trafficking enterprise. It resonated with the president, who had campaigned on stemming the flow of drugs into the country, according to a senior administration official.
In August, the U.S. doubled the reward for the arrest of Maduro to $50 million. "Under President Trump's leadership, Maduro will not escape justice and he will be held accountable for his despicable crimes," Attorney General Pam Bondi said.
In his first term -- when he unsuccessfully tried to topple the autocrat with oil sanctions -- Trump had similarly considered a variety of options, including military ones. But he was met with pushback from the Pentagon. Defense officials never developed detailed plans to execute military strikes, according to Juan Cruz, the top White House official handling Latin American policy in Trump's first term.
This time, the Pentagon moved quickly to operationalize Trump's orders to execute military strikes in the region. In September, the Trump administration launched a military campaign to bomb alleged drug-smuggling vessels in the Caribbean and eastern Pacific, an effort that has killed more than 110 people. That was followed by the largest military buildup the region has seen in decades, with an aircraft carrier, naval strike vessels, logistical ships and thousands of Marines amassing off the coast of Venezuela.
The lethal action and massive deployment, as well as the White House's shifting rationales for what it was seeking to accomplish in Venezuela, triggered scrutiny from U.S. lawmakers on both sides of the aisle.
"I want to know what's going to happen next. Is it the policy to take Maduro down? It should be if it's not," Sen. Lindsey Graham (R, S.C.) said late last year, calling the administration's Venezuela policy confusing after a closed-door briefing with Rubio and Hegseth.
Trump administration officials publicly denied that the pressure campaign was about regime change, contending that it was an effort to stem the flow of deadly narcotics to the U.S.
But by late summer, senior officials began drawing up options to remove Maduro from power. Rubio, Hegseth, CIA Director John Ratcliffe, homeland security adviser Stephen Miller and Dan Caine, the chairman of the Joint Chiefs, began to meet regularly to discuss the potential operation.
U.S. intelligence personnel started to closely track Maduro -- where he went and lived, what he ate and wore -- with the aid of an asset in the Venezuelan leader's inner circle, according to administration officials and others familiar with the operation. U.S. special operations forces began to do dry runs of the extraction, practicing on a replica of his Caracas compound at a military base.
By the fall, Trump had told Grenell to stop his diplomatic outreach to Venezuelan officials, and Grenell has been sidelined since then, administration officials said.
In October, Trump made the unusual announcement that he had authorized the CIA to conduct covert operations in Venezuela, alleging the country's leaders had "emptied their prisons into the United States of America" and "we have a lot of drugs coming in from Venezuela."
Maduro, who denied the allegations, retorted that the U.S. was trying to justify an invasion to loot Venezuela's natural resources, something he had warned about his entire political career. "They want us to become slaves of the empire again. Never!" Maduro said. People close to his government said the strongman, after overcoming pressure during Trump's first term, saw the U.S. threats as a bluff.
Weeks later, Trump privately expressed reservations to aides that ordering a military operation to remove Maduro might fail to force him out, U.S. officials said at the time.
In mid-November, the two leaders spoke on the phone. They discussed general amnesty for Maduro, his senior aides and their families, many of whom face U.S. financial sanctions and criminal indictments, people familiar with the matter said. Trump told Maduro that if he didn't leave willingly, the U.S. would consider the use of force, according to people familiar with discussion.
A few weeks later, opposition leader María Corina Machado made a daring escape from the country, slipping through military checkpoints to reach a fishing boat bound for Curaçao and a private jet headed to Norway, where she was honored with the Nobel Peace Prize. The U.S. military was kept apprised of the operation, according to people involved in her escape.
Trump allies lauded the escape as the next step to help Machado's opposition movement take over Venezuela.
On Dec. 23, there was a final attempt to allow Maduro to voluntarily step down to live in exile. He turned it down.
"He was provided multiple very, very, very generous offers, and chose instead to act like a wild man, chose instead to play around," Rubio told reporters Saturday. "And the result is what we saw tonight."
Write to Vera Bergengruen at vera.bergengruen@wsj.com, Juan Forero at juan.forero@wsj.com, Kejal Vyas at kejal.vyas@wsj.com and Alex Leary at alex.leary@wsj.com
(END) Dow Jones Newswires
January 04, 2026 21:03 ET (02:03 GMT)
Copyright (c) 2026 Dow Jones & Company, Inc.
