When President Trump turned to the Capitol gallery during his State of the Union speech in February to recognize Venezuela’s young opposition leader, Juan Guaidó, it seemed like a political masterstroke.
Mr. Guaidó’s surprise appearance — the culmination of efforts by foreign policy hawks to shift U.S. strategy in Latin America and dislodge Venezuela’s strongman president, Nicolás Maduro — prompted a standing ovation from Republicans and Democrats alike. “Maduro’s grip on tyranny will be smashed and broken,” Mr. Trump proclaimed. In the 2020 battleground of South Florida, home to hundreds of thousands of Venezuelan expatriates and Cuban-Americans who support their cause, Mr. Trump’s embrace of Mr. Guaidó drew a rapturous response.
But on the eve of Election Day, Mr. Trump’s approach to Venezuela has yielded both some political success and a foreign policy failure. While recent polls show Mr. Trump running close to his Democratic rival, former Vice President Joseph R. Biden Jr., among Florida’s Latino voters, his administration’s harsh sanctions have failed to oust Mr. Maduro, while leaving Chinese, Russian and Iranian interests more firmly entrenched in Venezuela. Mr. Maduro has effectively vanquished Mr. Guaidó, whose popular support has collapsed.
Mr. Maduro’s survival is, in part, a parable of foreign policy in Mr. Trump’s Washington — where ideologues, donors and lobbyists compete to seize the attention of an inexperienced and highly transactional president, warping and reshaping American diplomacy along the way.
The tug-of-war over Mr. Trump’s Venezuela position pitted Cuban-American activists and Florida politicians, who viewed Mr. Maduro as a proxy and energy supplier for Cuba’s Communist regime, against pro-Trump business interests advocating closer engagement with Mr. Maduro.
They included a billionaire donor from Florida; top lobbyists who have earned millions in the influence-business boom of Mr. Trump’s first term; and a Venezuelan oligarch, now under federal indictment, who worked to broker U.S. investments in his country.
At stake was not only the welfare of Venezuelans, but also the flow of billions of dollars in their country’s crude oil — and, Mr. Trump came to believe, his re-election prospects.
As Mr. Maduro endures, a key architect of Mr. Trump’s Venezuela policy left his White House post in September. The same month, another official met secretly in Mexico with a Maduro ally in a last-ditch effort to persuade Mr. Maduro to step down — which Mr. Trump could have touted as a triumph before November.
A White House spokesman, John Ullyot, said Mr. Trump’s leadership had led to broad international pressure on Mr. Maduro. “The president continues to support the Venezuelan people to ensure a future that is democratic and prosperous,” he said.
But some former officials who favored a tougher stance on Venezuela now question the administration’s approach.
“There is a very strong consideration for the donors, for the swing voters in Florida and for those that are just ideologically pure on the evilness of Cuba,” said Fernando Cutz, who worked on the National Security Council for Mr. Trump and his predecessor. “The nuance is gone — the diplomacy.”
In spring 2017, Brian Ballard, a lobbyist and top Trump fund-raiser from Florida, hosted a meeting with two people who would play a role in the struggle over Venezuela’s future.
One was Raúl Gorrín, who had amassed a fortune under Venezuela’s socialist government while building close ties to both Mr. Maduro and the opposition. He was among a wave of foreign interests reaching out to Mr. Ballard, who had recently opened a Washington office to meet the demand for lobbyists close to the new administration.
The other guest was Mauricio Claver-Carone, a longtime lobbyist on Cuba policy and a ferocious defender of the embargo. He had landed at the Treasury Department after working on the Trump campaign but had ambitions for a foreign policy role. Mr. Claver-Carone declined to comment.
As the two men talked alone, their conversation grew testy, according to Mr. Gorrín, 51. Mr. Claver-Carone insisted that the regime was close to collapse; Mr. Gorrín argued that Mr. Maduro was firmly in control and that the United States and Venezuela would benefit from a thaw.
“You don’t know Venezuela,” he recalled saying.
Mr. Trump, a mutual object of interest, had unformed views but was curious about Venezuela, piqued by its vast oil wealth and by the country’s dominance of the Miss Universe contest, which he once owned, according to two former White House aides.
He was also focused on re-election. “Trump saw Venezuela 110 percent through the prism of Florida’s electoral votes,” said a former senior U.S. official, who requested anonymity to characterize private conversations.
Mr. Trump heard often from Marco Rubio, the Cuban-American senator from Florida, who advised tougher sanctions. Under Mr. Maduro’s leadership, the economy of the once-wealthy country had cratered, its health system failed and opposition was often met with violence.
But Mr. Trump swung between belligerence that unnerved even his hawkish aides and supreme confidence in his negotiating skills. In summer 2017, while musing publicly about invading Venezuela, he also asked advisers whether he should meet with Mr. Maduro, according to one of the aides.
“We were always fearful that he would want to exercise that option,” said the former aide, speaking on the condition of anonymity. “You can’t say no. We said, ‘It’s going to be bad for your image, and he’s going to manipulate you.’”
That summer, Mr. Gorrín’s media company hired Mr. Ballard. Both men agree that Mr. Gorrín wanted help placing his Globovisión network on American television, where it might grow into a Spanish-language Fox News. Associates of Mr. Gorrín said he also hoped the lobbyist could establish him as a player in Washington on Venezuela policy, making key introductions. (Mr. Gorrín said Mr. Ballard proposed the middleman role; the lobbyist denied that and said he made no introductions.)
The Venezuelan said that Mr. Ballard connected him to Harry Sargeant III, a billionaire Trump donor from Florida who had worked in Venezuela in the 1990s. Mr. Sargeant, 62, saw Venezuela’s oil reserves as a business opportunity and the key to energy independence for the Americas.
Mr. Gorrín, in turn, helped arrange for Mr. Sargeant to meet state oil company officials in Caracas; when he arrived, he found himself in a session with Mr. Maduro as well. In an interview, Mr. Sargeant said he told Mr. Maduro that Venezuela needed American businesses to help rebuild its economy.
Soon after, one of Mr. Sargeant’s companies began negotiating a deal to take over three dilapidated oil fields. In summer 2018, Mr. Sargeant flew with an associate to see Mr. Trump at a New York fund-raiser, trying — unsuccessfully — to deliver a letter from Mr. Maduro.
In Washington, the hard-liners had been gaining ground. Mr. Trump fired Rex W. Tillerson, his secretary of state, in early 2018 and installed John Bolton, a veteran hawk, as national security adviser. In the White House, Mr. Rubio’s view — maximum pressure on Mr. Maduro — prevailed, with the State Department playing a diminishing role.
After Mr. Maduro won a second term in an election widely denounced as a sham, the Trump administration imposed new sanctions.
With support from Mr. Rubio and others, Mr. Bolton hired Mr. Claver-Carone that August to run Western Hemisphere affairs on the National Security Council. The administration began preparing economic penalties that would target Mr. Maduro’s inner circle and the oil assets he depended on for hard currency.
Later that fall, Mr. Claver-Carone met Mr. Sargeant for drinks near the White House. Mr. Sargeant had recently finalized the oil deal, one of the most favorable that Venezuela had granted to a foreign business in years. Mr. Maduro had allowed the project, he told Mr. Claver-Carone, to show that he wanted better relations with the United States.
Mr. Claver-Carone was unmoved, Mr. Sargeant recalled. There was only one message the official wanted to hear from Mr. Maduro: where the Venezuelan president wanted to live in exile, whom he wanted to accompany him and how much money he wanted to take.
In early 2019, the White House rallied an international coalition to recognize Mr. Guaidó, head of Venezuela’s National Assembly, as the country’s rightful president. Speaking to a Miami crowd that February, Mr. Trump urged the Venezuelan military to back Mr. Guaidó or “lose everything.”
By then, according to two Venezuelan opposition leaders and a former Trump administration official, Mr. Claver-Carone and others were pressing Venezuela’s military and political elite to turn on Mr. Maduro.
“He had to deliver a win,” the former administration official said. “He sold it to the president as, ‘if you get rid of Maduro, you win’” in Florida.
Among those Mr. Claver-Carone contacted, according to the opposition leaders, was Mr. Gorrín.
By then, he was technically a fugitive from American justice. The prior summer, U.S. prosecutors had charged him in an alleged money-laundering scheme. He dismissed the indictment as political persecution, but Mr. Ballard had dropped him as a client and Mr. Gorrín was added to the sanctions list.
Now, American officials and the Venezuelan opposition needed back channels of their own. According to the opposition leaders, Mr. Gorrín and other intermediaries were asked to convey U.S. offers of leniency to cooperative regime figures.
Mr. Gorrín had attended university with the chief justice of Venezuela’s supreme court; the Americans believed they had a deal with Mr. Gorrín to help deliver the judge and others to Mr. Guaidó's side. That March, the Trump administration quietly took Mr. Gorrín’s wife off the sanctions list.
Mr. Gorrín, whose discussions with regime figures were reported by The Wall Street Journal last year, denied playing any role in the effort, and said he had no contact with Mr. Claver-Carone after their 2017 meeting.
An attempted uprising failed. The promised supreme court ruling never materialized. Mass demonstrations led by Mr. Guaidó fizzled, and Mr. Maduro deployed paramilitaries to torture and kill protesters.
Mr. Sargeant, whose oil deal had been scuttled by the new sanctions, saw an opening. That summer, he teamed up with Robert Stryk, a lobbyist who had earned millions representing foreign leaders in Washington. Mr. Stryk’s White House contacts told him that the president felt misled by his advisers on Venezuela. Eager to cut foreign policy deals that administration hawks opposed, Mr. Trump was clashing with Mr. Bolton. By September, he was gone.
The next month, Mr. Sargeant and Mr. Stryk flew to Caracas to meet with Mr. Maduro. When they arrived in the presidential palace, there was another guest: Mr. Gorrín.
Mr. Maduro seemed to brush off reports of Mr. Gorrín’s role in the failed April uprising. “He’s my guy,” Mr. Maduro remarked, according to another person present at the meeting. Mr. Maduro waxed about American baseball and said he was willing to let U.S. drug enforcement agents back into the country.
Mr. Stryk proposed a plan to secure formal legal representation for Mr. Maduro in Washington — a revived diplomatic channel. Mr. Maduro picked up a Trump figurine made of chocolate and mimed shaking his hand.
“We’re all having a meeting now,” he said.
Nothing would come of the effort. After Mr. Stryk and a law firm filed disclosure forms revealing their proposed work for the regime, the blowback was severe. Senator Rick Scott, a Florida Republican, pledged to blackball all the firm’s clients unless it withdrew. It did.
The Trump administration’s drive to unseat Mr. Maduro also faltered. He brushed off a White House proposal in March that he and Mr. Guaidó step aside in favor of a transitional government.
Mr. Maduro’s opponents grew desperate. In May, a group of radical opposition sympathizers, former military officers and American mercenaries tried to invade Venezuela by speedboats. The operation was ambushed. The attempted coup became a political one for Mr. Maduro, when documents linked one of Mr. Guaidó’s advisers to the putsch.
In scripted settings, Mr. Trump has remained committed to his administration’s hard-line policies. In a July appearance in Florida, he contrasted his attacks on Mr. Maduro with what he characterized as the socialist-friendly policies of Mr. Biden.
But in an interview with Axios in June, Mr. Trump had distanced himself from Mr. Guaidó, and suggested he was open to meeting Mr. Maduro. The president’s Twitter feed, once filled with denunciations of the Maduro regime, went all but silent on the topic this fall. By then, Mr. Claver-Carone was on his way out, to an influential job running the Inter-American Development Bank.
“It is a shame where we are right now,” said Steve Goldstein, a former top State Department aide to Mr. Tillerson. “Maduro should not be the president of Venezuela.”
Patricia Mazzei and Edward Wong contributed reporting.