The international call came in September 2018, after months of rising tension between the United States and Venezuela, a key strategic player in South America.
On one end of the line was Venezuela's socialist president, the pariah leader of a disintegrating economy whom President Donald Trump's administration was seeking to isolate.
On the other end: the U.S. president's personal attorney Rudy Giuliani and then-Rep. Pete Sessions, R-Texas.
Both were part of a shadow diplomatic effort, backed in part by private interests, aimed at engineering a negotiated exit to ease President Nicolás Maduro from power and reopen resource-rich Venezuela to business, according to people familiar with the endeavor.
Sessions had served as emissary in the back-channel effort, visiting Maduro in Caracas that spring. The phone call, which Giuliani joined, was a follow-up to that visit, Sessions' spokesman Matt Mackowiak told The Washington Post.
The phone conversation involving the Venezuelan president and Trump's personal lawyer, which has not been previously reported, provides another example of how Giuliani used his private role to insert himself into foreign diplomacy, alarming administration officials confused about whose interests he was representing.
Giuliani operated a similar campaign this year in Ukraine, where he pressured officials to announce investigations to benefit Trump - an endeavor that led to the president's impeachment this month.
The impeachment inquiry pushed into the spotlight consulting work Giuliani has undertaken around the globe even as he has been representing Trump at no charge. His freelancing has triggered concerns among White House officials that his intercessions have muddied and at times undercut official U.S. policy, according to people familiar with the worries, who, like others cited in this story, spoke on the condition of anonymity to describe internal discussions. Meanwhile, federal prosecutors are scrutinizing the former New York mayor as part of an investigation into possible foreign lobbying violations.
Word of Giuliani's call with Maduro eventually reached White House officials, who did not know why he was involved, according to one former senior administration official.
Giuliani's willingness to talk with Maduro in late 2018 flew in the face of the official policy of the White House, which, under national security adviser John Bolton, was then ratcheting up sanctions and taking a harder line against the Venezuelan government.
Around the time of the phone call, Giuliani met with Bolton to discuss the off-the-books plan to ease Maduro from office - a plan Bolton vehemently rejected, two people familiar with the meeting said.
Giuliani did not respond to multiple requests for comment. A lawyer for Bolton declined to comment. The White House did not respond to requests for comment.
In January 2019, the United States formally recognized Maduro's rival Juan Guaidó as president, a policy move backed by Bolton. Later in the year, Giuliani would pick up a client in the region: a Venezuelan tycoon under investigation by the Justice Department for possible money laundering.
It is not clear why Giuliani became involved with the back-channel negotiations with Venezuela's president or the extent of his role. But the tale of behind-the-scenes talks with Maduro offers another example in which the president's personal attorney aligned with private interests to try to sway U.S. foreign policy. And the episode involves some of the figures who played a role in the Ukraine effort - including Sessions, an 11-term congressman who pushed for the ouster of the U.S. ambassador to Ukraine around the time he met with Giuliani associate Lev Parnas in 2018.
Sessions, who lost his seat that November and is now running for Congress in another Texas district, said through his spokesman that he has known Giuliani for three decades but has never worked with him on any private-sector activities.
WhenTrump took office, he promised to take a tougher stand against Maduro, who has been Venezuela's president since the 2013 death of leader Hugo Chávez and has grown increasingly repressive, even as his country has sunk into economic crisis.
That approach had the backing of Republicans in Florida, which has large and politically engaged Venezuelan and Cuban communities. Sen. Marco Rubio, R-Fla., accused then-President Barack Obama of failing to hold Maduro accountable and of naively pursuing negotiations that failed to remove him from office.
Trump's personal interest in the country was piqued by a February 2017 White House visit by Lilian Tintori, the wife of a prominent Venezuelan political prisoner. She was also a former kite-surfing champion who had appeared in that country's version of the reality show "Survivor."
Trump quickly adopted Venezuela as a cause, surprising some in the human rights community who noted he did not show similar interest in abuses in countries such as North Korea and Russia.
That year, the Trump administration labeled Venezuela's vice president a drug kingpin and froze his assets in the United States. It also imposed economic sanctions on Venezuelan companies and banned travel to the U.S. by government officials and their families.
"This corrupt regime destroyed a prosperous nation by imposing a failed ideology that has produced poverty and misery everywhere it has been tried," Trump declared before the United Nations General Assembly in September 2017. "To make matters worse, Maduro has defied his own people, stealing power from their elected representatives to preserve his disastrous rule."
Conditions worsened in Venezuela, where there were frequent shortages of basic goods including food and medicine, runaway inflation and spates of civil unrest. But Maduro remained in power.
In February 2018, Maduro announced that a presidential election would be held that spring. But most opposition candidates would be banned from running, leading to fears that the vote would be a sham election used to consolidate his power.
U.S. business executives with interests in Venezuela, among them Harry Sargeant III, the chief executive of a Florida-based global energy and shipping company who has worked extensively in the country, began encouraging negotiations to ease Maduro out of office.
In a statement, Sargeant said he "supported the idea of a back channel based on my over 30 years of firsthand experience in Venezuela and my observation of the political dynamic going on in Caracas at the time."
"I believed then and now that an adversarial sanctions policy alone would have two profoundly negative effects," he added. "First, it would exacerbate Venezuela's humanitarian crisis. Second, I believed it would undermine key U.S. business interests in Venezuela to the benefit of American adversaries like the Russians and Chinese."
It was against this backdrop that Mackowiak said Sessions accepted an invitation from Maduro to quietly visit Caracas and try to negotiate a path to improved relations between the United States and Venezuela.
Sessions, a former chairman of the National Republican Congressional Committee who chaired the House Rules Committee at the time, had long been interested in Venezuela, in part because many of his Texas constituents had energy interests there, according to his spokesman.
"He was pleased to help with this back-channel mission, which was coordinated with the highest levels of the U.S. State Department," Mackowiak said, adding that Sessions met with top U.S. officials before and after his trip.
The State Department did not respond to requests for comment.
But people familiar with State Department officials' role said those officials did not initiate the trip or organize or participate in Sessions' meeting with Maduro. And several U.S. officials disputed the notion that the trip was sanctioned, noting that the White House at the time wanted to take a harder line with Maduro and was not interested in making concessions.
National Security Council officials, in particular, were opposed to the kind of settlement with Maduro that Sessions was advocating.
"There was absolutely no interest or appetite for negotiations," said a former White House official. "We generally did not welcome efforts like this one. It wasn't consistent with our policy goals. We saw it as a nuisance and a distraction."
Sessions' spokesman dismissed such complaints as part of a "turf battle" among Washington bureaucrats.
"There might have been a disagreement between the State Department and the NSC about how best to bring peace to Venezuela," Mackowiak said. "But Rep. Sessions was pleased to be part of an effort, coordinated closely with the State Department, to bring a democratically elected president to Venezuela."
Sessions' district is home to ExxonMobil and other oil companies that were once active in Venezuela but were forced to scale back amid political turbulence. But Sessions told the Dallas Morning News in 2018 that the oil interests did not play a role in his decision to become involved. He said he had been working with various players, including representatives of the Venezuelan opposition, to negotiate a solution for more than a year.
Sessions told the newspaper he was working to make "dialogue between parties that are trying to make progress."
Mackowiak said Sessions used his own funds to pay for the two-day trip.
Two people with knowledge of the visit said he was hosted by Raúl Gorrín Belisario, the owner of a major television network in Venezuela who was viewed with distrust by some U.S. officials and months later would be indicted in Florida on charges of money laundering and bribery.
The people said that rather than staying in a U.S. facility, Sessions stayed at Gorrín's lavish, modernist, walled compound in a fashionable part of the capital.
Mackowiak said that Sessions' trip, including where Sessions stayed, was coordinated with State Department officials.
Sessions left Caracas with a list of concessions that had been agreed to by Maduro - his departure from power and a commitment to allow free and fair elections in exchange for leniency from the United States - according to Mackowiak.
But some U.S. officials said they worried that the deal Sessions was floating was intended to legitimize the upcoming election by opening up the vote to at least some opposition candidates, which could help Maduro remain in power, rather than ease him from office, according to a person familiar with the conversations. And they were concerned that the back-channel overtures sent mixed messages to the Maduro government.
About five weeks after returning from Caracas, Sessions met in his Capitol Hill office with Parnas, who Mackowiak said wanted to discuss a proposal to sell liquefied national gas in Ukraine.
In an indictment this fall charging Parnas and his business partner Igor Fruman with illegally channeling foreign money into U.S. election campaign accounts, federal prosecutors said Parnas sought Sessions' assistance in ousting then-U.S. Ambassador to Ukraine Marie Yovanovitch at the behest of "one or more Ukrainian government officials."
On May 9, the same day that Parnas posted photos of his meeting with Sessions on Facebook, the congressman sent Secretary of State Mike Pompeo a letter urging Yovanovitch's removal.
Mackowiak said Sessions did not act at the request of Parnas but wrote the letter after hearing concerns about the ambassador from several members of Congress who had traveled to Ukraine.
Meanwhile, in Venezuela, Maduro won re-election in May with nearly 68 percent of the vote. The international community largely rejected the vote because of allegations of fraud and the banning of key opposition parties, and civil unrest ensued as Maduro prepared to begin another term.
In August, U.S. prosecutors charged Gorrín, Sessions' host for the congressman's Venezuela visit, with participating in a $1 billion money-laundering and bribery scheme. Prosecutors have said Gorrín is a fugitive. Neither Gorrín nor his Miami-based lawyer responded to requests for comment.
Around that time, Giuliani, who had joined Trump's legal team months earlier, began talks with individuals who were part of the back-channel to Maduro. In August, Giuliani met in New York with Parnas and two American business executives with investments in Venezuela to discuss the effort, according to people familiar with the gathering.
The meeting took place at a favorite Giuliani hangout, the Grand Havana Room cigar bar, blocks from Trump Tower in Manhattan. Over whiskey and cigars, Giuliani agreed to try to see whether there was a way to negotiate with Maduro and perhaps reach a diplomatic solution to the political chaos and economic collapse overtaking the country, one of the participants said.
About a month later, Maduro was on the phone with Sessions. In the room with the Venezuelan president at the time was the country's first lady, who serves as a close adviser to her husband, as well as Venezuela's vice president and information minister, according to a person familiar with the conversation.
Giuliani was introduced at the beginning of the call but appeared mostly to listen as Maduro and Sessions spoke, Mackowiak said.
In the nearly hour-long conversation, they reviewed the concessions that Maduro had agreed to make during Sessions' visit months earlier, according to the person familiar with the call.
The communications ministry of Venezuela did not respond to a request for comment.
Later, word filtered to the White House that Giuliani and Sessions had participated in a call with Maduro, causing confusion, said a former senior administration official.
"We didn't know why Rudy was involved at the time," the person said.
Not long after the call, Giuliani told some of his associates that he had taken the idea of a soft landing for Maduro to Bolton, the president's national security adviser. But he said the meeting had not gone well, according to people familiar with his account.
Charles Cooper, a lawyer for Bolton, declined to comment.
Bolton's distaste for Giuliani's foreign policy freelancing emerged during the impeachment inquiry. Former national security official Fiona Hill testified that Bolton warned her not to interact with the president's lawyer, calling him "a hand grenade who's going to blow everybody up."
In January of this year, the situation in Venezuela disintegrated as Maduro prepared to be formally inaugurated for another term. The legislature, led by Maduro's opposition, declared that the election had been illegitimate and named legislative leader Guaidó the nation's new president. He was quickly recognized by the United States and dozens of other countries.
Some Venezuelan business leaders who had amassed vast wealth under Maduro but had been severely constrained by U.S. sanctions switched sides and began to assist Guaidó.
Among them was Gorrín, who played a key role in a failed effort to persuade the nation's Supreme Court to recognize Guaidó over Maduro, part of an effort to curry favor with the Americans, as The Post has reported.
This summer, another wealthy Venezuelan energy executive, Alejandro Betancourt López, hired Giuliani to serve as his lawyer and help argue that he should not be charged in a $1.2 billion money laundering case in Florida.
Eight men - including Betancourt's cousin - have already been charged in the case, which alleges that top officials of the Venezuela's state-owned oil company, business leaders and bankers conspired to steal money from the company and then launder it through Miami real estate purchases and other investment schemes. Two people familiar with the matter said that Betancourt is referred to in the criminal complaint as an uncharged co-conspirator.
Jon Sale, a Miami-based lawyer representing Betancourt, has said his client denies any wrongdoing. He declined to comment on Betancourt's relationship with Giuliani.
In early August, Giuliani was hosted at Betancourt's lavish estate outside Madrid when Giuliani met at Trump's direction with a top aide to the Ukrainian president, as The Post previously reported.
Giuliani later met with Justice Department officials and urged them not to charge Betancourt, The Post reported.
In response to questions about his work for Betancourt, Giuliani wrote in a text message last month: "This is attorney client privilege so I will withstand whatever malicious lies or spin you put on it."
The news that Giuliani was representing the wealthy energy executive before the administration while also serving as the president's personal attorney disturbed veteran U.S. officials who have experience in Venezuela.
"You have to ask, 'Why is he doing this?' " said one former senior administration official.
This article was written by Rosalind Helderman, Tom Hamburger, Anthony Faiola and Josh Dawsey, reporters for The Washington Post.