Half a year prior to the deployment of US troops to capture Venezuelan President Nicolas Maduro, President Donald Trump favored a diplomatic arrangement over a forcible deposition. The Wall Street Journal reports that the commander-in-chief initially sought a pact centered on prioritizing American petroleum interests.
During a July Oval Office meeting, Trump informed advisers he preferred continuing negotiations with Maduro's administration to secure terms prioritizing US petroleum corporations seeking Venezuelan crude extraction – choosing diplomatic engagement over confrontation, according to The Wall Street Journal.
Trump recognized Secretary of State Marco Rubio, who had persistently cautioned against trusting Maduro and argued petroleum income would strengthen his administration, opposed this approach. Yet Trump, according to sources familiar with the conversation, insisted on pursuing an agreement: "We're doing it my way."
By late December, the president opted for military intervention, exhausted by repeated attempts to convince Maduro to resign in exchange for immunity from alleged crimes, The Wall Street Journal stated. The audacious overnight mission that concluded Saturday with Maduro imprisoned in New York served as a test case for more forceful foreign policy Trump has indicated he may deploy elsewhere, from Colombia to Greenland.
Throughout Trump's second administration, Venezuela rapidly became an unexpected nexus of his objectives – large-scale deportations, drug trafficking, the appeal of vast petroleum and mineral reserves, and sustained pressure from Rubio, son of Cuban exiles, and other hawks to overthrow its oppressive regime, according to The Wall Street Journal.
"Venezuela is a perfect storm, it's everything the Trump administration is concerned about," stated Elliott Abrams, who managed Venezuelan affairs during Trump's first term, The Wall Street Journal reported.
Trump's fixation on the nation's assets, expressed to associates after his second inauguration, sparked internal maneuvering among advisers and petroleum lobbyists over Venezuela policy, according to The Wall Street Journal. Trump made clear he prioritized a transaction from Caracas advancing his America First agenda, including deportation cooperation and favorable petroleum terms, over pushing democratic transition.
Ultimately, Rubio and Trump's other hawkish advisers prevailed after persuading the president that Maduro represented a drug-trafficking extremist who wouldn't relinquish power voluntarily, The Wall Street Journal stated.
From his perspective, Maduro viewed Trump's pressure campaign as empty posturing, according to former aides and businessmen close to the regime, The Wall Street Journal reported. "President Donald Trump, you must be careful because Marco Rubio wants to stain your hands with blood," he stated in September, denouncing US pressure as an effort to commandeer the nation's resources.
Maduro appeared in videos dancing and singing at holiday events, telling Americans – in broken English – he wanted peace and "don't worry, be happy." Trump privately expressed frustration about the videos, telling aides he considered Maduro unserious, a senior administration official stated, according to The Wall Street Journal.
On December 23, Maduro rejected what he didn't realize would be his final resignation offer, The Wall Street Journal reported. Instead of living his remaining days in exile with family, a helicopter transported him and his wife from Caracas into US custody.
Trump – currently – has cautiously embraced the Venezuelan leader's second-in-command, Delcy Rodríguez, after advisers informed him the ambitious 56-year-old socialist might prove more receptive to collaborating with US companies, according to The Wall Street Journal.
When Trump returned to the White House last January, he felt he had invested excessive time and political capital attempting – and failing – to oust Maduro during his first term, according to former officials, The Wall Street Journal stated.
The matter quickly reentered his attention, The Wall Street Journal reported. Many Trump top allies viewed Maduro's hold on power as lingering humiliation, and evidence Washington was tolerating an openly antagonistic regime in its hemisphere, former US officials stated.
A deal-oriented president who had never embraced the Venezuelan opposition, Trump assigned one of his most reliable aides on complex international matters, Richard Grenell, to lead, according to The Wall Street Journal.
The instructions were straightforward: secure American hostages' release held by Venezuela's regime, obtain opportunities for American petroleum corporations, and persuade Maduro to accept planeloads of Venezuelan migrants the Trump administration wanted to deport, The Wall Street Journal stated. Maduro had stopped accepting deportation flights in early 2024 as talks with the Biden administration collapsed.
It appeared effective, according to The Wall Street Journal. Just 11 days into Trump's term, Grenell flew to Caracas and posted photos shaking hands with Maduro at the Miraflores presidential palace. That day, he returned with six Americans the US claimed had been wrongfully detained. Deportation flights resumed, regularly departing the US to Caracas each 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 tracking deportation flights, The Wall Street Journal reported. The deportations were promoted in flashy videos by the White House, which claimed it was deporting gang members and criminals.
During its opening months, the Trump administration continued promoting a hard line on Venezuela publicly, according to The Wall Street Journal. Mauricio Claver-Carone, Trump's then-envoy for Latin America, insisted there was no "quid pro quo" with Maduro.
"It's not a negotiation in exchange for anything," he told reporters last January, The Wall Street Journal stated. "We don't need Venezuelan oil."
Rubio warned the president that the Venezuelan leader had made five deals with different administrations over the past decade and had broken all of them, according to a Rubio aide, The Wall Street Journal reported.
Trump decided to offer Maduro an exit, according to The Wall Street Journal.
In May, the US offered Maduro a deal to leave Venezuela for life in exile in exchange for amnesty shielding him from drug charges, according to people familiar with the matter, The Wall Street Journal stated. The sanctions against him and some other regime officials would be lifted and the US in turn would work with a transition government, the people stated. One person stated there were early discussions about the government being led by Vice President Rodríguez.
The strongman rejected that offer, plus similar subsequent ones, according to The Wall Street Journal.
As US officials juggled priorities on Venezuela, petroleum remained paramount, The Wall Street Journal reported. Energy companies were pushing intensely to convince the government to ease sanctions, which they claimed were excluding Americans from lucrative petroleum deals and recouping billions in debts while giving China greater influence in the hemisphere and stoking outward migration from an economically devastated Venezuela.
In July, Chevron regained the ability to pump petroleum in Venezuela, reversing a move earlier that year to rescind a Biden-era license, according to The Wall Street Journal.
Petroleum industry lobbyists were fighting for additional companies to return to the country, The Wall Street Journal stated. They told Trump administration officials that the regime in Caracas was so desperate that they would welcome US firms with enticing terms not seen by the industry in decades – including no-bid contracts and minimal environmental or regulatory oversight. But US officials were cautious that striking business deals while allowing Maduro to remain 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 homeland security adviser Stephen Miller, emphasized to Trump that US prosecutors had charged Maduro with heading a drug-trafficking enterprise, according to The Wall Street Journal. It resonated with the president, who had campaigned on stemming the drug flow into the country, according to a senior administration official.
In August, the US doubled the reward for Maduro's arrest to $50 million, The Wall Street Journal reported. "Under President Trump's leadership, Maduro will not escape justice and he will be held accountable for his despicable crimes," Attorney General Pam Bondi stated.
In his first term – when he unsuccessfully tried to topple the authoritarian with petroleum sanctions – Trump had similarly examined various options, including military ones, according to The Wall Street Journal. But he was met with Pentagon pushback. 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 rapidly to operationalize Trump's orders to execute military strikes in the region, The Wall Street Journal stated. 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 witnessed in decades, with an aircraft carrier, naval strike vessels, logistical ships and thousands of Marines amassing off Venezuela's coast.
The lethal action and massive deployment, plus the White House's shifting rationales for what it sought to accomplish in Venezuela, triggered scrutiny from US lawmakers on both political sides, according to The Wall Street Journal.
"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," Senator Lindsey Graham (Republican, South Carolina) stated late last year, calling the administration's Venezuela policy confusing after a closed-door briefing with Rubio and Pete Hegseth, The Wall Street Journal reported.
Trump administration officials publicly denied that the pressure campaign concerned regime change, contending that it constituted an effort to stem deadly narcotics flow to the US, according to The Wall Street Journal.
But by late summer, senior officials began developing options to remove Maduro from power, The Wall Street Journal stated. Rubio, Hegseth, Miller, CIA Director John Ratcliffe and Dan Caine, the chairman of the Joint Chiefs, began meeting regularly to discuss the potential operation.
US intelligence personnel started closely tracking Maduro – where he traveled and lived, what he consumed and wore – with aid from an asset in the Venezuelan leader's inner circle, according to administration officials and others familiar with the operation, The Wall Street Journal reported. US special operations forces began conducting extraction dry runs, practicing on a replica of his Caracas compound at a military base.
By fall, Trump had instructed Grenell to cease his diplomatic outreach to Venezuelan officials, and Grenell has been sidelined since, administration officials stated, according to The Wall Street Journal.
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."
Smoke raises at La Carlota airport after explosions and low-flying aircraft were heard in Caracas, Venezuela, Saturday, Jan. 3, 2026 (AP Photo/Matias Delacroix)
Maduro, who denied the allegations, retorted that the US was attempting to justify an invasion to plunder Venezuela's natural resources, something he had warned about his entire political career, The Wall Street Journal stated. "They want us to become slaves of the empire again. Never!" Maduro stated. People close to his government stated the strongman, after surviving pressure during Trump's first term, viewed the US 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, US officials stated at the time, according to The Wall Street Journal.
In mid-November, the two leaders spoke by phone, The Wall Street Journal reported. They discussed general amnesty for Maduro, his senior aides and their families, many of whom face US financial sanctions and criminal indictments, people familiar with the matter stated. Trump told Maduro that if he didn't leave willingly, the US would consider force, according to people familiar with the 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, according to The Wall Street Journal. The US military was kept apprised of the operation, according to people involved in her escape.
Trump allies praised the escape as the next step to help Machado's opposition movement take over Venezuela, The Wall Street Journal stated. On December 23, there was a final attempt to allow Maduro to voluntarily step down to live in exile, according to The Wall Street Journal. He declined.
"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, The Wall Street Journal reported. "And the result is what we saw tonight."
