Nicolas Maduro is seen in handcuffs after landing at a Manhattan helipad, escorted by heavily armed US federal agents as they make their way into an armored car en route to a Federal courthouse in Manhattan on January 5, 2026 in New York City. Photo / Getty Images NEW YORK, NY - JANUARY 5: Nicolas Maduro is seen in handcuffs after landing at a Manhattan helipad, escorted by heavily armed Federal agents as they make their way into an armoured car en route to a courthouse in Manhattan on January 5 in New York City. Photo / Getty Images
On Christmas Eve, Cardinal Pietro Parolin, second in command to the Pope and a longtime diplomatic mediator, urgently summoned Brian Burch, the United States ambassador to the Holy See, to press for details on America’s plans in Venezuela, according to government documents obtained by the Washington Post.
Would the US target only drug-traffickers, he asked, or was the Trump Administration really after regime change?
Nicolas Maduro had to go, Parolin conceded, according to the documents, but he urged the US to offer him a way out.
For days, the influential Italian cardinal had been seeking access to US Secretary of State Marco Rubio, the documents show, desperate to head off bloodshed and destabilisation in Venezuela.
In his conversation with Burch, a Trump Administration ally, Parolin said Russia was ready to grant asylum to Maduro and pleaded with the Americans for patience in nudging the strongman towards that offer.
“What was proposed to [Maduro] was that he would go away and he would be able to enjoy his money,” said a person familiar with the Russian offer.
“Part of that ask was that [Russian President Vladimir] Putin would guarantee security.”
It was not to be.
A week later, Maduro and his wife Cilia Flores would be seized by American Special Operations forces in a raid that killed about 75 people and be flown to New York to face drug-trafficking charges.
The previously unreported meeting in Vatican City was one of many failed attempts - by the Americans and intermediaries, the Russians, Qataris, Turks, the Catholic Church and others - to head off a building diplomatic crisis and find safe harbour for Maduro before the US raid to capture him just over a week ago.
“It is disappointing that parts of a confidential conversation were disclosed that do not accurately reflect the content of the conversation itself, which took place during the Christmas period,” the Vatican press office said in a statement to the Post.
Burch’s spokesperson referred questions to the State Department, which declined to comment. Kremlin spokesman Dmitry Peskov did not respond to a request for comment.
This story is based on interviews with nearly 20 people, many of whom spoke on the condition of anonymity to discuss sensitive talks and intelligence.
It includes new details about the far-reaching global efforts to steer Maduro into exile and avoid US military intervention, as well as the Trump Administration’s decision to work with Venezuela’s sitting vice-president, rather than the opposition leader Washington had long supported.
The weeks and months leading up to that day included missed opportunities for Maduro, a former bus driver and one of Latin America’s last caudillos, who appeared unaware of how perilous his position had become.
His rejection of multiple possible off-ramps, even as US warships began striking alleged narco-trafficking boats off the Venezuelan coast and US officials intensified their rhetoric against his government, would ultimately seal his fate.
Attempts to secure a way out for Maduro continued until the 11th hour.
He would receive a final warning just days before the US operation to capture him, according to a person familiar with the offer. But the autocrat refused to budge.
“He wasn’t taking the deal,” another person said. “He was just going to sit there and watch people create a crisis.”
All the while, the US was homing in on a plan for his successor, leaning into Maduro’s No. 2 - Delcy Rodriguez.
It was a striking about-face for US President Donald Trump, who during his first term had sanctioned Rodriguez and her powerful brother, Jorge, seen in Washington at the time as interchangeable members of Maduro’s ruling cabal.
But a more pragmatic view began to take hold as leading members of the Administration questioned the ability of opposition leader Maria Corina Machado to successfully win over the military and other bases of power long controlled by followers of the late Hugo Chavez, founding father of the country’s socialist state.
Trump’s thinking was partly influenced by a recent classified CIA assessment, which concluded that Maduro loyalists would be more successful in running a post-Maduro government than Machado and her team, according to a senior White House official and a person familiar with the matter.
The substance of the assessment, first reported by the Wall Street Journal, found that Machado would struggle to overcome pro-regime security services and was relayed to Trump by CIA Director John Ratcliffe, the senior White House official said.
Soon afterwards, the official added, Trump settled on Rodriguez as Maduro’s successor at the recommendation of his top intelligence and security officials.
For years, Rodriguez had a public persona as a fiery Chavista, but in one-on-one encounters, particularly with US oil representatives, she came off as a totally different person.
“She wasn’t anti-American; she’d even lived in Santa Monica” in her college years, said one person who held repeated conversations with her. “She was the farthest thing from an ideologue.”
There is no indication that Rodriguez was aware of the US plot to remove Maduro.
And the Trump Administration did not tell her that she had become the favourite to take his place, the senior White House official said.
It would have been “extremely dangerous for us to communicate anything prior to the operation”, the official said.
Maduro, for his part, seemed to consistently misunderstand the signals from Washington.
He believed a November call he had with Trump had gone “well”, said a person familiar with his thinking, when in fact he was being told his time was up. “The President said you can go the easy way or the hard way,” the senior White House official said.
Trump even invited his Venezuelan counterpart to Washington, according to a source, offering safe passage so they could discuss matters in person. Maduro turned him down.
He calculated that the Democrats would win the Midterm elections, that Trump would be hamstrung - and that he could cling to power.
“He was out there dancing,” the person said. “Not anymore.”
The Vatican has long been a spoke in the wheel of international negotiations with Venezuela’s isolated Government.
A decade ago, the Holy See tried and failed to work out a deal between Maduro and the fractured opposition.
More recently, the Vatican had sought dialogue with the Venezuelan Government through its senior clerics in the country, and Pope Leo XIV had cautioned the Americans against the use of force.
“I believe violence never brings victory,” Leo said in November after mentioning reports of US warships moving towards Venezuela. “The key is to seek dialogue.”
Parolin, who had previously served as the papal nuncio - or Vatican ambassador - to Caracas, had a deep interest in Venezuela.
He had also served as an intermediary with the Trump Administration before on Ukraine and Russia, according to a person familiar with the negotiations.
Venezuela represents an important foothold for Moscow in Latin America.
When Chavez rose to power in 1999, Venezuela made major purchases of Russian weapons, including tanks, Sukhoi fighters and surface-to-air missiles.
Russia also offered significant loans to Caracas, provided financial lifelines to help the country weather US sanctions and remains a player in the Venezuelan oil industry.
In his December 24 meeting with Burch, according to the documents obtained by the Post, Parolin said Russia was prepared to receive Maduro.
He also shared what is described in the documents as a “rumour”: that Venezuela had become a “set piece” in Russia-Ukraine negotiations, and that “Moscow would give up Venezuela if it were satisfied on Ukraine”.
Analysts say Russia had already reduced its support for Venezuela in recent years as its focus shifted to the war next door.
Loans to help Venezuela buy Russian weapons effectively stopped in 2018.
When Maduro visited Moscow in May, he signed a strategic partnership agreement with Putin, but the relationship was viewed by most observers as more ideological than substantive.
Russia’s apparent offer to grant asylum to the Venezuelan president came amid broader efforts by Moscow to reset relations with the US and secure a favourable deal on Ukraine.
The documents show Parolin told Burch that he believed Maduro had been willing to step down following the July 2024 election, which the Venezuelan leader was widely believed to have stolen.
But he was convinced then by Diosdado Cabello, his hardline Interior Minister, that doing so would cost him his life.
Parolin said Maduro would have become hesitant to leave without the support of his inner circle, according to the documents, and was probably concerned about abandoning his top lieutenants, notably Rodriguez and Cabello.
The person familiar with the Russian offer, however, said Moscow was also willing to grant asylum to the other senior Venezuelans, and it appeared that Maduro was simply digging in his heels, believing the US would not act.
“I think it was hubris,” this person said.
Another factor may also have been at play.
The assessment among some in Washington was that Maduro would never go to Russia because it was too restrictive - and he wouldn’t have access to the money from the Venezuelan gold trade he is believed to have stashed offshore, according to a person familiar with the deliberations of the Trump Administration.
Parolin suggested that the US could set a deadline for Maduro’s exit from the country, the documents said, and provide assurances for his family.
The cardinal expressed that he was “very, very, very puzzled by [the] lack of clarity of the US endgame in Venezuela”, the documents say. He appealed for patience, caution, restraint.
But the White House was done with waiting.
Rodriguez, the daughter of a leftist who died in the custody of Venezuela’s intelligence services, was a longtime senior socialist who rose to the highest ranks under Maduro and became an indispensable figure in his inner circle.
As Oil Minister, she served as a high-level emissary on sensitive foreign missions to Turkey and Qatar and became a reliable partner for oil interests and other foreign investors in Venezuela - even as she helped Maduro co-opt democracy and solidify his authoritarian rule.
Rodriguez began gaining the trust of some in the Caracas business community in recent years by reforming the economy, improving the exchange rate and working with a team of young people - including economists from the government of Rafael Correa when he was Ecuador’s president.
She received pushback from inside the Maduro Government for her reforms, particularly from Flores and from hardliners in the Chavista establishment who had benefitted from the country’s entrenched power structure.
Officials from Chevron, the only American company Washington had permitted to operate in Venezuela amid US sanctions, met monthly with Rodriguez and spoke positively about her to the US Government, including under the Biden administration, a former American diplomat said.
The Chevron model was working, US officials were told by company representatives, and Rodríguez was granting their wishes.
Asked for comment, a spokesperson for Chevron said the company had no advance notice of the US military operation and did not engage in any discussions with Administration officials regarding governance for a post-Maduro Venezuela.
Venezuelan business leaders began to push for Rodriguez as a person who could lead a political transition. “That consensus seems to have been accepted up in Washington,” according to a person familiar with the Maduro Government.
The vice-president had also emerged as an effective manager in talks with Qatar, a fellow Opec member and a key intermediary with Venezuela in recent years.
Qatar had “a lot of frustration” with Maduro, who would overrule things to which his negotiators agreed, according to a Biden official familiar with the talks.
The Qatari assessment was that if Rodriguez “says she’s going to do something, it gets done”. The Qataris “recognised that Delcy should run the country before anybody else did” if Maduro was out, the former official said.
A spokesperson for the Qatari Government did not respond to a request for comment.
Early last year, Trump’s presidential envoy for special missions, Richard Grenell, took a leading role in negotiating with Venezuela, sometimes with the help of Qatar and sometimes directly with Rodriguez’s brother, Jorge Rodriguez, a psychiatrist, former minister of information and current president of the country’s national assembly.
In those talks, Venezuela repeatedly shot down US proposals for Maduro to leave power, according to a person familiar with the discussions.
At one point, the Venezuelans suggested Maduro could step down and stay in the country while Rodriguez took over, the person said, but it was never a “concrete” proposal.
And by the late northern summer, it became clear that Rubio - a Venezuela hawk and Grenell rival who has always favoured pressure over negotiations - was taking over the Venezuela file. Grenell did not respond to a request for comment.
During an Oval Office meeting on October 2, the senior White House official said, Trump and his top aides discussed how else they could apply pressure on Maduro, beyond the boat strikes that have killed more than 100 people in the Caribbean and Eastern Pacific.
Trump applauded Grenell’s diplomatic efforts to coax Maduro to step down, but he said it was time for military action, the White House official said.
Over the following months, Qatar received multiple Venezuelan requests for talks with the US, according to a person familiar with the outreach, but the Trump Administration indicated it was not interested.
Unofficial emissaries filled the void. They included Brazilian billionaire Joesley Batista, who arrived in the Venezuelan capital of Caracas in late November on a mission to convince Maduro to leave power.
Among the points discussed that day was a plan for the president to step down, according to three people familiar with the meeting.
Maduro was given an offer to go into exile to Turkey or another willing country, two of the people said. The Turkish Embassy in Washington did not respond to a request for comment.
A potential asylum deal for Maduro in Turkey had been in play since at least November, according to the person familiar with Trump Administration deliberations, including “guarantees” he would not be extradited to the US.
But the now-jailed former leader and his wife indignantly pushed back, the three people said.
“Nicolas Maduro had multiple opportunities to avoid this,” Rubio said during an appearance with Trump at Mar-a-Lago.
“He was provided very, very, very generous offers and chose instead to act like a wild man, chose instead to play around.”
Batista, a beef magnate with business interests in both the US and Venezuela, had previously acted as a middleman in negotiations over tariffs that Trump had imposed on Brazilian goods.
He arrived in Caracas with a list of four points - including insistence on American access to rare metals and oil, a break with Cuba - Venezuela’s longtime ally - and Maduro’s departure from the country, according to a person familiar with the meeting.
After the trip, Batista relayed his takeaways to the Trump Administration, the senior White House official said.
He “was not working at the behest of the US”, the official said, but it took his findings “into consideration”.
Rodriguez knew that, according to the constitution, she would take over on an interim basis in the event of a Maduro’s exit from the political stage, according to a person in contact with the Venezuelan Government.
When the issue was brought up, she would become “uncomfortable”, the person said.
In the end, though, she would have no say in the matter.
As momentum built around the idea of working with Rodriguez, US officials began to sour on the prospect of a future government led by Machado - Venezuela’s most prominent opposition leader and the winner of the 2025 Nobel Peace Prize.
In recent weeks, influential business executives in Venezuela and even other members of the country’s opposition movement had warned the US that Machado had not made enough inroads with the armed forces - the ultimate arbiters in Venezuela - and would not be capable of gaining their trust, according to additional US government documents obtained by the Post.
In conversations with US diplomats about her plans should Maduro suddenly leave power, those documents show, Machado’s team expressed a belief that most of the military would fall in line, and it had assured military contacts it would avoid a broad purge of troops.
Her advisers told US officials they would not need to prosecute more than a few dozen regime figures. But they also made clear that top Maduro officials would have no place in a new government.
In the documents, US officials described discussions with other contacts who expressed scepticism about the inroads Machado’s team claimed to have made with the armed forces.
One member of the Venezuelan opposition said there had been no conversations between her representatives and military officers.
Taken together, the contacts were worried that in the event of Maduro’s abrupt departure, “a Machado-led government would flounder in the face of immense challenges”.
Machado’s team did not respond to requests for comment. In the aftermath of Maduro’s seizure, the opposition leader has sought to assuage Trump, including offering to give him her Nobel Peace Prize, an award he has openly coveted.
Her decision to accept the prize, people close to the White House have said, contributed to Trump’s decision to turn against her.
Machado is expected in Washington this week, the US President told Fox News on Friday. “I look forward to saying hello to her,” Trump said, adding that it would be “a great honour” to accept her award.
In the documents, US officials included an analysis that now seems prescient: “Should Maduro suddenly depart the scene and other senior Chavistas were to stay in power, they might well decide to keep their repressive regime going to maintain their ill-gotten riches and avoid the justice that awaits them”, they wrote.
Rodriguez has striven to consolidate power since Maduro’s departure, vacillating between defiant and conciliatory tones toward Washington. Authority is fractured in Venezuela, and early signals have been mixed.
The detention of journalists and civilians, as well as new checkpoints set up by paramilitary gangs, have been interpreted by analysts as a show of strength by Cabello, who controls the country’s intelligence services and police.
The Trump Administration remains confident in its decision to back Rodríguez, pointing to Friday’s release of some political prisoners and an agreement to export Venezuelan oil to the US.
“We have seen thus far immense, deep co-operation with the interim authorities,” said the senior White House official, noting that Rodriguez and Rubio speak “frequently”.
It was a lesson, said a person close to the Maduro Government, “that it is not possible to govern Venezuela without Chavismo”.
At the Vatican, Leo expressed concern that “a diplomacy that promotes dialogue” was being replaced by “diplomacy based on force”.
“War is back in vogue, and a zeal for war is spreading,” he warned.
- Ana Vanessa Herrero, Marina Dias, Stefano Pitrelli, and Tara Copp, Warren P. Strobel and Souad Mekhennet contributed to this report.
Sign up to Herald Premium Editor’s Picks, delivered straight to your inbox every Friday. Editor-in-Chief Murray Kirkness picks the week’s best features, interviews and investigations. Sign up for Herald Premium here.