Two days after taking office in January 2017 President Donald Trump surprised White House staff by asking for a briefing on Venezuela. At the time, Fernando Cutz was on the National Security Council staff as the President's Director for South America.

“For whatever reason, and honestly I don’t know what the reason was, but President Trump started on Day One, literally on Day One, asking about Venezuela. So, it was a priority of his from the very start,” Cutz told a forum at the Wilson Center, a Washington think tank, after he left government last year.

Cutz didn’t know, but the seed was planted a few days before Trump’s inauguration during a casual meeting at Trump Tower in New York. Trump had invited some South Florida friends to pay him a visit, among them Freddy Balsera, a Cuban American Democrat, who represented the real estate mogul on several South Florida golf projects.

During the meeting, Trump asked Balsera for some advice on what South Floridians would like to see from his presidency, according to witnesses. Balsera mentioned taking a tougher line on the Maduro regime in Venezuela, adding it would have bipartisan support and could make for a good foreign policy victory.



The president’s son-in-law and close advisor, Jared Kushner, was in the room and his ears picked up, the sources said. Balsera told Trump and Kushner about Venezuela’s most famous political prisoner: Leopoldo Lopez. And he had a suggestion: “You should meet with his wife, Lilian Tintori,” he said.

That’s precisely what happened a few weeks later, courtesy of another Cuban American - a Republican this time - Senator Marco Rubio.

Tintori was at the White House to meet Vice President Mike Pence and press the administration to do more about human rights in her home country. Tintori made her case during the 40-minute meeting. First lady Melania Trump, who was also in the room, expressed her sympathy.

In the midst of the meeting, Trump tweeted “Venezuela should allow Leopoldo Lopez … out of prison immediately.”



So, why was Trump’s meeting with Lilian Tintori so important?

Treading carefully



For the eight years under President Barack Obama, the U.S. chose to tread cautiously with Venezuela’s fiery President Hugo Chavez, who enjoyed strong support among the poor. U.S. officials feared that punitive actions, such as oil sanctions, might cause a backlash with familiar accusations of foreign meddling by the ‘gringo imperialists.’

Instead, they banked on the socialists coming unstuck at home due to their own misrule. But for years the opposite occurred, especially when oil prices soared, hitting $120 a barrel in 2008.

In 2013 the socialists suffered a massive blow. Their charismatic leader, was struck down by cancer. Chavez was replaced by political ally Nicolas Maduro, a loyal acolyte but lacking the same popular appeal.

By the time Trump entered the White House things had really begun to fall apart in Venezuela. Corruption was rampant, mismanagement at the state oil company had seen output fall dramatically. Oil prices had also plummeted. And to cap it off Maduro and his allies were using PdVSA as their personal piggy bank, pocketing billions of dollars in the process, according to a series of major federal indictments in New York, Houston and South Florida.



Maduro’s regime was rapidly losing legitimacy at home – while a flood of refugees was creating big problems for his neighbors in the region. The Trump administration saw an opportunity. The stars were aligning in the region with leftist governments in Brazil and Colombia moving to the right.

“A lot of it was a continuity of the vision that folks under President Obama had, but we were given the green light to act,” said Cutz.

Obama had begun to impose sanctions on some top Venezuelans. The Obama White House even looked at oil sanctions, but decided the moment wasn’t right.

That changed soon after the Trump administration took office as violence on the street of Caracas mounted, and evidence of corruption piled up.

An ‘escalatory roadmap’



“The plan that we designed was a step-by-step approach that was getting stronger as the situation on the ground warranted. It was a designed program of escalation, an ‘escalatory roadmap’ as we called it,” said Cutz.

“It listed these certain actions that … we would take based on what was happening on the ground,” he added. “We were given full freedom and liberty to go through the possibilities, and that was critical, because we had that top cover from the President who really cared about this."

Trump intensified the sanctions regime.

In the summer of 2017, Venezuela was rocked by street demonstrations.

In photos: Violence and repression in Venezuela reaches shocking new levels after month-long protests Cargando galería



In August 2017, Trump went as far as announcing that the “military option” was on the table.

The Trump administration also began to raise the rhetoric, calling Maduro a dictator, and a ‘madman.’



But it wasn’t until 2018 that Trump assembled a new more hawkish foreign policy team. Out went Secretary of State Rex Tillerson and National Security Council Advisor General HR McMaster. In came conservatives Mike Pompeo and John Bolton.

'Little Marco' gains influence



Rubio’s influence has also grown since that White House visit with Lilian Tintori. Despite calling him ‘Little Marco’ during the 2016 presidential campaign, Trump has now taken to heaping President Donald Trump has lately taken to heaping praise on his former presidential rival.



“I do listen a lot to Senator Rubio on Venezuela, it’s close to his heart,” Trump told a small group of reporters representing regional news outlets last month.

Rubio was also instrumental in bringing into the government some key Cuban Americans; Mauricio Claver-Carone at the NSC. Another John Barsa, is awaiting confirmation to lead USAID’s operations in Latin America. Claver-Carone is a longtime activist on Cuba policy and staunch backer of the economic embargo against Havana’s communist government.

Barsa, who enlisted in the U.S. Special Forces reserves, previously worked for another Cuban American congressman in Miami, Lincoln Diaz-Balart.

In an exclusive interview with Univision, Claver-Carone said the U.S. wasn’t interested in negotiating with Maduro, unless it was to discuss his exit. "What we are not willing to have is a conversation about how he can go on wasting time and usurping power," he said.





Cuba in the crosshairs



Otto Reich, another conservative Cuban American and former U.S. Ambassador to Venezuela says the Trump administration clearly has Cuba in its sights.

"I think that what they are preparing in the government is first of all to use the fall of the Venezuelan dictatorship that has financed so much violence and subversion in the hemisphere, to later bring about changes, transitions in Cuba and Nicaragua," he told the Jaime Bayly show last month.

Meanwhile, U.S. policy shift dovetailed with a new unified purpose among Venezuelan opposition leaders, who began to put together a ‘Made in Venezuela’ national reconstruction plan, dubbed, ‘Plan Pais, para el dia despues.’ (The Country Plan, for the day after)





The situation on the ground took an important turn in May 2018 when Maduro sought re-election for another six years. With the main opposition leaders either disqualified or jailed the election was declared a fraud. When Maduro was sworn in January 10 this year, the opposition denounced his presidency as illegitimate, creating a new constitutional crisis.

Guaidó enters the picture



That grew on January 23, when Juan Guaidó, the largely unknown president of the National Assembly, was sworn in as interim president.

Trump administration officials say they had been waiting for this moment. For the first time in 20 years, U.S. officials could argue there was a rightful president they could put their support behind.







In mid-December, Guaidó had quietly traveled to Washington, Colombia and Brazil to brief officials on the opposition’s strategy of renewed demonstrations to coincide with Maduro’s swearing-in. In a trip over the New Year’s holidays, U.S. Secretary of State Mike Pompeo met with his Brazilian and Colombian counterparts.

With the support of an international coalition backing Guaidó, the US is now hell bent on a plan to oust Maduro, and hold new elections. Part of the strategy is to use a massive humanitarian relief effort to test the loyalty of the Venezuelan military.

But it’s a high-risk strategy.

“The people of Venezuela, are we going to make them suffer more than they are right now? And if the answer to that is yes, then you need to really be careful," warns Cutz.

"Will the United States be solely on the hook to fix Venezuela if we do that? Yes, absolutely, because then everybody in the region, everybody in Venezuela, will point to the United States and say, ‘This is your mess,’” he adds.