WORLD NEWS
01/21/2020 05:45 EST | Updated 01/21/2020 05:45 EST

The Man (And The Mission) Behind Trump’s Clash With Venezuela

Ousting Venezuelan leader Nicolás Maduro is Trump's dream and NSC official Mauricio Claver-Carone is eager to make it come true.

Illustration: Rebecca Zisser/HuffPost; Photos: Getty
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At a campaign-style rally in Miami last February, President Donald Trump issued a clear warning to Nicolás Maduro, the socialist leader of Venezuela whom Trump had wanted to oust from the day he entered the White House two years prior. “A new day is coming in Latin America,” Trump proclaimed, taking aim at not only Maduro but also the remnants of Fidel Castro’s regime in Cuba.

To casual observers, it was easy to spot the influence of John Bolton in the president’s increasingly hawkish approach to the Americas. Bolton, whom Trump had named his national security adviser the previous spring, had declared the leftist governments of Venezuela, Nicaragua and Cuba the “Troika of Tyranny.” Just weeks earlier, Trump had recognized Venezuelan opposition leader Juan Guaidó as the country’s interim president, openly declaring the United States’ intention to end the Maduro regime — with military force, if necessary.

But veteran foreign policy hands in Washington and South Florida also saw the fingerprints of another lesser-known adviser with a hardline track record and the sort of sharp rhetorical tongue that had defined Trump’s — and Bolton’s — recent approach to Latin America. Trump’s speech, many of those experts thought, sounded like it had been written by Mauricio Claver-Carone. 

Claver-Carone, who serves as Trump’s top Latin America adviser on the National Security Council, is little known outside Washington. But he is notorious within the city’s Latin America circles as a bulldog for the hardline community that favors ever tougher stances toward Cuba’s ruling regime and still sees the region as the key front for Cold War-esque battles against creeping communist threats. To them, the Cubans are the puppet masters behind the instability gripping the Americas, in Venezuela and beyond; to them, the only answer is the sort of relentless pressure they believe has never been adequately applied to the region’s rogue leaders, especially to the Cubans.

Trained as a lawyer, Claver-Carone has spent most of the last two decades as an influential lobbyist and chief antagonist of anyone ― including former President Barack Obama ― who seeks to roll back the nearly 60-year embargo that has still not achieved its stated aim of ending Communist rule in Cuba. But under Trump he moved inside the government, and for the last 16-plus months, Claver-Carone has enjoyed unrivaled influence over the president’s policies toward Venezuela — so much so that foreign ambassadors have complained privately about his dominance on this issue. 

The president has exhibited a simplistic obsession with Maduro since he entered the White House, and it has only deepened amid the economic crisis that has sparked an 8,000% increase in the number of Venezuelan refugees and threatened to destabilize the entire region.

But Trump’s push for aggression shocked even those inside the foreign policy apparatus who’d long craved the chance to take a more forceful approach. “I’m a hawk in inter-agency meetings, but in the Oval Office, I’m the dove,” one senior official used to lament to his colleagues as he left meetings in which Trump demanded military options or more antagonistic policies toward Maduro than his advisers recommended. 

Trump’s facile and inconsistent view of the world has left even those closest to him baffled, wondering why a president so willing to cut up a negotiated deal with Iran favors dialogue in North Korea or how a leader who espouses the need to draw down military commitments in the Middle East has been so eager to start another one in South America. 

Searching for coherence in Trump’s foreign policy is a quest to discover “something that just isn’t there,” said Fernando Cutz, who served on the NSC under both Obama and Trump. “It’s going to be country by country, item by item. And even then it might not be consistent.”

The president’s foreign policy is, at its core, guided by the same narcissism that drives his decision-making on any other issue: Trump wants to win. And in Venezuela, coercion is his only strategy.

Gabriel Aponte via Getty Images
With Trump's blessing, Mauricio Claver-Carone is pursuing the "maximum pressure" strategy he and other hardliners believe necessary against Venezuela.

Where others ― including Bolton, whom Trump fired in September last year in part for “holding me back” on Venezuela ― have had to compromise to work in that environment, Claver-Carone is living his dream. He has the opportunity to implement the “maximum pressure” strategy he and other hardliners have long believed necessary in Venezuela, the backing of a president who shares that view, and the mandate to ensure the rest of the government helps Trump ramp up the pressure to its actual maximum, too.

Apparently, they still haven’t reached it, even a year after the strategy began in earnest with the recognition of Guaidó.


“If you’d asked me in January 2017, ‘Who is the worst person who could be in that senior director position,’ I would have said, ‘Him!’” Ben Rhodes told HuffPost last year of Claver-Carone. (Rhodes had spearheaded Obama’s efforts to normalize U.S. relations with Cuba.) 

It’s not an uncommon view: Claver-Carone is not the sort of regional generalist or experienced diplomat who has typically occupied his NSC position, and he has little expertise on the largest countries in the Americas ― a concern nearly a dozen Latin America policy experts or former government officials expressed in interviews with HuffPost. Claver-Carone has spent his career focused almost entirely on Cuba, with occasional forays into U.S. relations with the socialist governments in Venezuela and Nicaragua, which he and many other anti-Castro hardliners see as little more than puppets of the Cuban government. 

“It is mind-boggling that we’d have a policy driven by these three countries, while overlooking Brazil, Chile, Argentina, Mexico,” said Christopher Sabatini, a global affairs professor at Columbia University and the founder of Global Americans, a Latin America-focused research nonprofit. “Imagine having an NSC director for Asia that knew nothing but Laos. That’s what we’re talking about. You’ve got Japan and the Koreas, China and Vietnam, and this guy only knows Laos. Imagine that.”

Claver-Carone declined to comment on the record for this story. 

Ariana Cubillos/ASSOCIATED PRESS
Trump's foreign policy advisers so far have not backed his idea of invading Venezuela to take out the country's socialist president, Nicolás Maduro. 

Claver-Carone is a born and bred anti-Castro warrior, brought up in South Florida by a Cuban American mother whose own family had been persecuted in Cuba after the revolution. He would “go berserk” at the mention of Fidel Castro, a high school friend once recounted to USA Today. As a student at Rollins College in Orlando, Claver-Carone would stay after class to discuss with his mentor “how naive people are” when it came to the Cuban regime, the paper reported. 

If Trump’s interest in Venezuela and Cuba is mostly, and maybe entirely, a cynical search for victory ― over Maduro and in Florida (and beyond) in the 2020 election ― Claver-Carone’s is the opposite. 

He is a true believer in the gospel that Cuba has been, and remains, the chief antagonist to freedom and prosperity in the Western Hemisphere; that the United States’ failure to deal with the Cubans has allowed them to act as a nefarious force across the region; and that the liberation of Cuba from Communist rule ― and thus the liberation of the people in countries influenced by Cuba ― should figure prominently in any U.S. president’s agenda. He has devoted his career to that cause.

After a brief stint as a Treasury Department lawyer in the George W. Bush administration, Claver-Carone launched a career as a Cuba policy lobbyist. It was a fraught time for pro-embargo interests. Public opinion in the U.S. had begun to shift, Congress had taken small steps toward loosening the restrictions, and the largest pro-embargo institution in Washington had splintered, leaving a void on the hardline side of the aisle. 

Claver-Carone’s first act as executive director of Cuba Democracy Advocates — a new nonprofit group launched by two wealthy Cuban American businessmen who wanted to fill that hardline void — was to commission a poll gauging support among Cuban American voters for the effort to ease restrictions on Cuba. The poll found that most respondents opposed any change in the U.S. approach to the island; in fact, it found that nearly half of young Cuban Americans wanted the U.S. to take military action against Castro. The survey earned media attention in Miami, though not all of it positive. Noting that the survey’s questions were overly leading, a polling expert derided it in the pages of Miami’s largest newspaper as “useless in determining attitudes toward Cuban policy.”

Claver-Carone also led the U.S.-Cuba Democracy PAC, a political action committee that throughout the 2000s has helped to blunt every bit of momentum toward loosening the embargo. Between 2004 and 2015, the PAC raised more than $4 million and made contributions to more than 600 campaign committees.

The first time the new Democratic Congress voted on Cuba in 2007, 66 Democrats — including multiple members of party leadership — voted down an effort to weaken the embargo. Fifty-two of them had received donations from Claver-Carone’s group.

By 2009, 18 members of Congress had changed their position on the embargo after receiving money from the U.S.-Cuba Democracy PAC, according to Public Campaign, a nonprofit that advocated for campaign finance reform. Between 2003 and 2009, the PAC’s supporters, individually and through the PAC, showered nearly $11 million on congressional candidates, Public Campaign said.

A third Claver-Carone-led organization, Cuba Democracy Public Advocacy Corp., was paid more than $250,000 to lobby Congress on various pieces of Cuba-related legislation between 2006 and 2016.

Claver-Carone’s efforts drew legal and ethical complaints from Citizens for Responsibility and Ethics in Washington, a liberal nonprofit watchdog, which alleged in four separate campaign finance complaints that the groups Claver-Carone oversaw had broken various laws. The most explosive claim was that the three organizations he led were improperly intertwined. But even as the Federal Election Commission raised concerns about practices in multiple cases, it never found Claver-Carone or the groups guilty of major violations, and it cleared him in the biggest case that CREW brought. So he pressed on.

Barack Obama won Florida in 2008 despite promising to meet with Raúl Castro, Fidel’s brother and successor, and carried the state again as he won reelection four years later. But Claver-Carone ― who had hosted a 2012 fundraiser at which GOP nominee Mitt Romney promised that, if he won, “Fidel Castro will finally be taken off this planet” ― was always a thorn in Obama’s side as the president moved to normalize relations with Cuba. 

Alongside his lobbying and other political activities, Claver-Carone ran Capitol Hill Cubans, a now-shuttered blog that was for years a must-read for anyone following U.S. policy on Cuba. He updated the blog daily as well as operating an email listserv to blast news to anyone who signed up. The site went offline when Claver-Carone joined the Trump administration. He also blogged for HuffPost: In 2015 he wrote that Obama’s policy of “talking for the sake of talking” had only “served as a useful distraction for the world” while the Castro regime strengthened “its political and economic grip over the Cuban people and their future.”

Almost everything [President Trump] did got terrible reviews in the press, except for Venezuela.A former Trump administration official

Rhodes, the former deputy national security adviser who ran point on the Obama administration’s Cuba efforts, always kept a close eye on Claver-Carone’s daily newsletters and blog posts. So, too, did the rest of the administration.

“I would read his blog and his blast emails because I found them to be the best barometer of what the furthest hardline reaction was to what we were doing,” Rhodes recalled. “We were very aware of him.”

“I thought of him as kind of a troll,” Rhodes said.

Others in the Cuban policy community were even harsher in their assessment. 

“He is a flamethrower who makes everything personal and political,” said James Williams, the executive director of Engage Cuba, a nonprofit that opposes the embargo. “If you view the U.S. embargo as an ineffective policy, you are going to be labeled very viciously by him as a Castro sympathizer, a regime lobbyist, a Castro bootlicker.” 

By 2015, the grassroots politics of Cuba policy had changed. In Florida, even the Cuban American community had soured on a harsh approach to the island, polls showed. But Claver-Carone’s lobbying firm ramped up its efforts, his PAC increased its contributions to candidates between 2014 and 2016, and congressional legislation to fully lift the embargo never progressed.

For Claver-Carone and his allies, the 2016 election presented a chance to elect a Republican who would unwind Obama’s limited rapprochement with Cuba and turn up the heat on the island government’s efforts to wield more influence across the hemisphere — especially in Venezuela.


Like many of the most senior officials in the current administration, Claver-Carone had not intended to work for Trump. At the outset of the 2016 GOP primary, he vocally backed Florida Sen. Marco Rubio, a longtime Capitol Hill ally, and Jeb Bush, the state’s former governor.

Either candidate, Claver-Carone believed, would immediately reverse Obama’s historic 2015 agreements with Cuba and further the goal of finally taking out the Castro regime.

It wasn’t just that Claver-Carone preferred his two fellow Floridians. He loathed Trump. Claver-Carone denounced the GOP front-runner on his blog as someone who “would place the moral, international leadership of the United States at risk” and savaged him in Twitter posts. He feared that Trump, who had once explored potential business opportunities in Havana and had never publicly displayed a particularly aggressive stance toward Cuba, would be an unreliable ally in the struggle against the Castros. Claver-Carone and the South Florida hardline community he came out of believed that the Castro regime could only be defeated with more pressure than the U.S. had ever applied, not less. 

ASSOCIATED PRESS
The Trump administration has piled sanctions on Venezuela in hopes of pushing the military to break with Maduro or fomenting a popular uprising against him.

Yet once it was clear that Trump would be the GOP nominee, Claver-Carone worked himself into the candidate’s good graces. He joined the Trump campaign as an adviser and began to influence the future president. In September 2016, Trump told a roaring Miami crowd that he would roll back Obama’s “concessions” to Cuba “unless the Castro regime meets our demands.” 

“Those demands are religious and political freedom for the Cuban people. And the freeing of political prisoners,” Trump said. 

“Is that right?” he asked the crowd.

It was. Trump’s language “could have come directly from Claver-Carone’s Capitol Hill Cubans blog,” USA Today later observed.

After Trump became president, Secretary of State Rex Tillerson blocked Claver-Carone, who’d worked on the transition team, from landing a job at the State Department, multiple sources said. Claver-Carone settled for a post at the Treasury Department. Later, he moved to the International Monetary Fund’s executive board. 

Meanwhile, some of Trump’s initial foreign policy advisers favored a more confrontational approach to Venezuela and Cuba than Obama had, especially as Venezuela’s economic collapse and hyperinflation threatened many of its people with poverty and starvation and sparked the refugee crisis that sent millions fleeing the country. But they were also hesitant to go along with the president’s harshest whims, including his suggestions that the U.S. just invade Venezuela to take out Maduro or his request for military options to do so. 

The U.S. instead focused on crafting a diplomatic approach that put a coalition of Latin American governments — known now as the Lima Group — out front in dealing with Maduro. And Trump, despite his campaign promises, only partially reversed Obama’s efforts to normalize relations with Cuba.

By August 2017, though, the administration had begun ramping up its own pressure campaign against Maduro with a new round of sanctions on key Venezuelan officials, which built on those Obama had imposed. While the sanctions weren’t the immediate success Trump had desired, they brought him good press. Many of the president’s earliest policy moves — immigration crackdowns, a ban on travelers from several Muslim-majority nations — had earned him judicial rebukes and sparked massive protests. So Trump, who is famously obsessed with how the media covers him, enjoyed the response on Venezuela. 

“Almost everything the president did got terrible reviews in the press, except for Venezuela,” a former Trump administration official said. “The Muslim ban — go down the list — they got slammed. And then when they started sanctioning Venezuelans, they got rapturous press. To some extent, they saw sanctions as the gift that keeps on giving.”

In March 2018, Trump suddenly fired both Tillerson and national security adviser H.R. McMaster. His decision to hire Bolton to replace McMaster drove several more moderate voices on Venezuela, including some holdovers from the Obama administration, to leave the White House. Similarly, advisers who’d favored diplomatic approaches to the crisis left the State Department either just before or immediately after Tillerson’s ouster. Several months later, Trump and Bolton installed Claver-Carone as the NSC’s senior-most adviser on the Western Hemisphere.

An old U.S. foe was fingered as a key culprit in Venezuela’s problems: the Cubans.

It was a victory for hardliners in Washington and Florida who had been disappointed in Trump’s initial slow-walking on Cuba and his lack of forceful action on Venezuela. Rubio, an ardent Cuba critic, had repaired his relationship with Trump and become something of a shadow secretary of state for the White House. Then in May 2018, Maduro won reelection in a race marked by irregularities, including his banishment of some opposition parties. The U.S. called the election “an insult to democracy” and hardliners believed it presented an opening for more aggressive action against the Venezuelan leader. 

Trump had “been very slow to act” in his efforts to “correct some (but not all) of the errors of the Obama administration” in Cuba and Venezuela, said Everett Briggs, a Reagan-era ambassador to Panama and Honduras and a prominent figure in the Cuba hardline community. The early days of Trump’s presidency were marked by a “general lassitude,” Briggs said, in making sure key positions were staffed “with individuals sharing the president’s outlook.”

Claver-Carone would help fix those problems, and more. To the hardline crowd, his hyperfocused career in Washington was proof not that he was inexperienced but that he was just what Trump needed.


On Jan. 23, 2019, Guaidó, the new leader of Venezuela’s National Assembly, declared himself the country’s legitimate constitutional president as well, citing fraud in the May 2018 election. 

The United States, which alongside the European Union and the United Nations had refused to recognize Maduro’s reelection, immediately and officially backed Guaidó’s claim of legitimacy ― a move that Bolton and Claver-Carone had urged Trump to take. More than 50 other nations, including influential Latin American governments, soon joined the White House. The international community was increasingly concerned about Maduro’s authoritarian tactics ― including violent crackdowns by secret police on opposition protests and imprisonment of political opponents ― and about the exploding refugee crisis in which more than 4 million Venezuelans have left the country, according to U.N. estimates.

The emergence of sympathetic right-wing governments in Brazil and other parts of the region also bolstered the Trump administration’s efforts, and it pushed the maximum pressure strategy harder. The U.S. piled more sanctions on specific Maduro officials, the Venezuelan government generally, and the pillars of the Venezuelan economy, including the state-owned oil company PDVSA. The idea was simple: Sanctions would force military officials loyal to Maduro to break with his regime. Or they would foment a popular uprising against him among angry Venezuelans.

ASSOCIATED PRESS
Juan Guaidó declared himself the country's legitimate leader on Jan. 23, 2019, and has since led the effort to oust Maduro.

An old U.S. foe, meanwhile, was fingered as a key culprit in Venezuela’s problems: the Cubans. During Trump’s February 2019 speech in Miami, a tirade ostensibly aimed at Venezuela that painted the fight to oust Maduro as a hemispheric struggle against socialism, Trump mentioned Cuba 18 times.

There is little doubt that Cuba has played some role in keeping Maduro afloat. The extent of Cuban involvement is the subject of debate across Washington, however, and few of the experts and officials who spoke to HuffPost for this story agreed with the White House’s view of the situation.

But since Claver-Carone joined the NSC, the Trump administration has missed no opportunity to steer Cuba policy hard to the right. It rolled back Obama’s normalization plans last summer, reinstating the travel ban for U.S. citizens and sanctions on the island itself. It even blocked Major League Baseball’s deal with Cuba to ensure the safe transfer of defecting players to the United States, and it tried to enlist the league in pushing Cuba to end support for Maduro.

Claver-Carone is not solely responsible for crafting the administration’s strategy, nor is he the only hardliner in charge: Just days after he recognized Guaidó, Trump appointed Elliott Abrams, the veteran neoconservative diplomat, as the State Department’s special envoy on Venezuela. 

But many in the hardline crowd, including those close to the White House, have credited Claver-Carone with crafting the administration’s more aggressive approach. With much of Trump’s foreign policy team, including Secretary of State Mike Pompeo, focused primarily on other threats, real or perceived, from North Korea and Iran, there was “a vacuum” on Latin America that Claver-Carone helped fill, said Otto Reich, the veteran hardliner who served as ambassador to Venezuela in the late 1980s.

Rubio, the Florida senator who has been credited with pulling the strings on Trump’s Latin America policy and who helped install Claver-Carone at the NSC, agreed with that sentiment last January. “Once Mauricio went in, the policy went on hyperdrive,” he told The New York Times.

To me, if you try a policy and after 60 years it doesn’t work, you shouldn’t try to replicate that policy.Fernando Cutz, a former National Security Council official

And Claver-Carone’s influence has only grown in the months since Bolton’s firing. That influence is apparent to foreign diplomats, too. In November, Colombia’s ambassador to the U.S. was caught on tape complaining that the State Department had lost much of its ability to shape Latin American policy and that “policy decisions are now primarily made” by Claver-Carone. 

Claver-Carone “has facilitated all of the processes inside the White House to increase the level of pressure” on Maduro, said Carlos Vecchio, Guaidó’s ambassador in Washington. “He’s one of the most important allies inside the administration.”


Survey foreign policy experts and former officials — from this administration and those previous — on what “victory” in Venezuela means to the White House, and various theories emerge. Few of them believe that the primary focus for Trump or his team is on alleviating a regional humanitarian crisis and restoring democracy in Venezuela, as the president and his officials so often insist.

Instead, some suggest that the White House sees the effort to oust Maduro as the first step toward finally breaking Communist rule in Cuba. Others posit that it’s a plot to energize Cuban and Venezuelan expats in South Florida ahead of the 2020 election. “Mauricio is a political operative,” another former senior Trump administration official said dismissively of Claver-Carone this past fall. Trump has tried to politicize the Venezuelan crisis: In the February 2019 speech in Miami, he lambasted Democrats as socialists and pointedly suggested that electing a Democrat in 2020 risked bringing “Venezuela-style socialism” to the United States. 

Whatever the motivation, there is little doubt that Claver-Carone has been successful in implementing the more aggressive approach that both he and the president favor. Last February, over the objections of the United Nations and the Red Cross, the U.S. launched a propagandistic humanitarian mission across the Colombian border into Venezuela that resulted in violent clashes between Guaidó supporters and the Venezuelan military. On April 30, 2019, the U.S. backed Guaidó’s failed military uprising against Maduro. In August, the Trump administration placed yet another round of sanctions on Venezuela, enacting everything short of a full embargo on the country. A month later, at the behest of the U.S., nations across the Americas invoked the Rio Treaty, a Cold War-era defense pact, in order to cooperate on sanctions against Maduro. In early December, they moved to make those sanctions even more aggressive, and the U.S. has called on Europe to toughen its sanctions as well. (“We need to increase the level of pressure from the international community,” Vecchio said.)

So far, the pressure hasn’t worked. Guaidó can generate anti-Maduro rallies with a single tweet, but he hasn’t been able to foster a sustained movement, and even though he remains popular among Venezuelans, much of the energy behind his efforts to dislodge Maduro seems to have fizzled. 

The U.S., meanwhile, appears to have overestimated the willingness of top Maduro officials to switch sides and underappreciated the complexities of the crisis. Maduro looks to be no closer to losing his grip on power today than he was three years ago, most of the experts who spoke to HuffPost agreed, a position that was bolstered when pro-Maduro lawmakers blocked Guaidó from entering the assembly and announced a new National Assembly leader this month.

The United States declared the leadership election illegitimate ― a position Abrams staked out even before the new year began, when he warned of fraud in the process during a December press conference at the State Department ― and said it still considers Guaidó to be the country’s constitutional leader. Regardless, it’s clear that Guaidó’s grip on the assembly has weakened one year after his declaration of legitimacy first suggested that Venezuela’s “new day” was imminent. 

The White House has continually pushed back on claims that Trump and other top U.S. officials believed the fight to oust Maduro would be an easy one. To hear them tell it, the problem is that their pressure cooker hasn’t reached its maximum yet. 

But many outside observers see an administration running thin on options with a strategy that isn’t all that strategic. “It’s maximum pressure for the sake of maximum pressure,” said Mark Feierstein, who served in Claver-Carone’s position on the NSC under Obama, echoing concerns that others have had from the outset. “There’s no strategy behind it.”

ASSOCIATED PRESS
A Maduro opponent carrying a Venezuelan flag covers his face against the tear gas fired during an attempted military uprising to oust the president on April 30, 2019.

Foreign policy observers have long warned that the United States’ excessive reliance on sanctions may have rendered them toothless, especially as their primary effect is to hurt ordinary people instead of the leaders they’re intended to punish or topple. And Maduro can look to other sanctioned regimes — in Iran, North Korea and, yes, Cuba — to see signs that he can outlast the Americans. 

“U.S. sanctions are a very effective way to demonstrate moral opprobrium, but historically they have not been an effective way to get regime change in other states,” said Daniel Erikson, a former State Department official and the author of “The Cuba Wars,” a detailed look at U.S. policy toward that nation. “If they want to demonstrate their extreme distaste and distrust for Venezuela and Cuba, sanctions can do that. What they can’t do is produce the policy outcome they want.”

The primary effect of the Venezuelan sanctions has been to exacerbate the human rights crisis for ordinary citizens. Continued food and medical shortages have forced ever more people to flee. The number of refugees could reach an estimated 8 million by the end of 2020, making this the worst migrant crisis in Latin American history.

U.S. officials have recently pushed back on the idea that sanctions are hurting the Venezuelan population. The administration that once emphasized swift action has also started to shift its focus to the long haul. Speaking of Venezuela in December, Pompeo noted that it took the Soviet Union more than 40 years to collapse and that U.S. efforts didn’t work “until they did.” 

There are key differences between Venezuela and Cuba, not least of which is that the United States is not isolated in its approach to Maduro the way it has been for decades in its anti-Castro strategy. Still, there is a growing risk that the administration’s strategy could turn Venezuela into a quagmire similar to the one that has occupied Claver-Carone throughout his life: with a sanction-heavy pressure campaign that remains in place because of political inertia and fears of appearing “soft” on an authoritarian regime, and not because it’s effective at alleviating the suffering of a crisis-stricken population or addressing the problems that may spread across the rest of the Americas. 

And the longer this strategy plays out, the harder it will be to change course for Trump — or anyone else, including a potential Democratic successor, most of whom support the broad outlines of the current approach. 

“To me, if you try a policy and after 60 years it doesn’t work, you shouldn’t try to replicate that policy,” said Cutz, the former NSC official. “We could have very well put ourselves in the box where 60 years from now, we have the same policies in place, everybody’s asking why we don’t like Venezuela, and no one can remember.”

“That’s the nightmare scenario,” Cutz added, “but I fear it might be heading in that direction.”

Claver-Carone and the president he serves are undeterred. In early January, the administration slapped even more restrictions on travel to Cuba. Pompeo said the United States made the move, in part, because of Cuba’s “unconscionable support” for Maduro and Venezuela.

It was yet another indication that the administration remains committed to its approach. The only problem Trump and his team appear to see with their maximum pressure strategy is that the “maximum” that will really do the job always lies just over the horizon.