Ten Years After Normalization With Cuba, Trump Hardliners Take Cuba Back In Time

A decade after Obama’s normalization, Trump’s team looks to ratchet up pressure on the island.

In October, we published a piece that ended up being one of the most circulated articles since our launch, a report by Ed Augustin from Havana examining how Biden administration policies toward Cuba have suffocated the island’s economy and drove a migration exodus. I’ve lost count of how many reprint requests we’ve gotten in how many different languages. I think what people appreciated is that it talked about Cuba and its place in the world honestly, and did so from the perspective of a reporter based there. There was no hagiography and the agency of the Cuban government was not ignored, and it didn’t just paint with a broad “it’s all America’s fault” brush, but instead explained in detail, how, in fact, it really is fundamentally all about a sweeping set of U.S. punitive policies aimed at immiserating the island in the hope of overthrowing the government.

Ten years ago, it looked like the U.S. had chosen a different course, when the Obama administration announced it would be normalizing relations with Cuba and turning the page on a failed Cold War confrontation. Now ten years later, sanctions and other hostile measures aimed at the island are greater than ever, and poised to get far worse, presenting the real possibility of the U.S. producing another failed state in the Caribbean. So we commissioned Ed to write another piece, this one explaining how we got from there to here, and where we may be headed.

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Marco Rubio and Donald Trump on October 29, 2024 in Allentown, Pennsylvania. Photo by Chip Somodevilla/Getty Images

By Ed Augustin

HAVANA — After two earthquakes, two hurricanes, and nationwide blackouts these last few months, Cubans thought things couldn’t get any worse.

Now, Cubans are now bracing for another Donald Trump presidency with Marco Rubio, the Cuban American Florida senator known for his hardline stance towards the island, his secretary of state. Other Cuban Americans on the Trump transition team have made clear that collective punishment of regular Cubans will be ratcheted up further.

It’s all a stark contrast to a decade ago, when President Barack Obama and Cuban President Rául Castro surprised the world with a historic announcement that the two countries would normalize relations. In Havana, church bells rang out, strangers hugged each other in the street, weeping with joy, and people partied late into the night. Obama consummated the new marriage by taking in a Cuban baseball game. It felt like the end of an era, the phasing out of an historical anachronism. As the Cold War faded, so too, it seemed, must the embargo.

Then came Trump. The first Trump administration bulldozed engagement, returning the U.S. to its historic posture of regime change towards the Cuban government, and cranking up the economic war against the island. Rather than revive the normalization process, the Biden administration, as Drop Site previously chronicled, doubled down on Trump’s policy.

How did the two countries get from the optimistic, heady days of 2014 to the desperate situation today?

From Breakthrough to Overthrow

In 2016, Obama became the first U.S. president to visit the island since Fidel Castro took power in 1959. He visited the re-inaugurated U.S. embassy in Havana, and connected so well with Cubans that people joked that if he were to stand in free and fair elections in their country, he'd win. Addressing Raúl Castro directly in the Grand Theatre of Havana, in a speech broadcast on the island, he said: “I believe my visit here demonstrates you do not need to fear a threat from the United States.”

“Obama changed the paradigm,” said Fulton Armstrong, the former National Intelligence Officer for Latin America, by “rejecting 60 years of failed efforts of forcing regime change in Cuba, and becoming open to peaceful coexistence and evolutionary change based on both countries’ interests.”

Critically, Obama went to Florida to argue the case. Though polls had consistently found that most Americans favored diplomatic and normal trade relations with the island, conventional wisdom was that, in the all-important battleground state of Florida, the hardline Cuban American diaspora would always oppose any detente with the regime. But a younger generation of Cuban Americans had started to break the taboo of returning to the island. In 2016, after both Obama and former Secretary of State Hillary Clinton had argued their case in Miami, polls showed for the first time that a narrow majority of Cuban Americans in South Florida favored the new Cuba policy.

After his election in 2016, Donald Trump started smashing normalization to pieces. He reportedly said there was one priority on Cuba: “Make Marco Rubio happy,” which resulted in the Florida senator choosing the personnel who wrote policy towards the country. Mauricio Claver-Carone, a former lobbyist who dedicated his career to hardening the sanctions, was installed in 2018 as senior director of Western Hemisphere Affairs at the White House’s National Security Council. He set about filling in the holes the Obama administration had punctured in the embargo.

Marco Rubio on Twitter in 2017: “Picture of the night @MarioDB and I hammered out the new Cuba policy.”

Claver-Carone also penned more than 200 new “maximum pressure” sanctions, which cranked up the economic war on the island to unprecedented heights. Title III of the 1996 Helms Burton Act was activated. This allowed Americans and U.S. corporations to sue companies that benefited from property they had owned before the Cuban government’s mass nationalization campaign in the 1960s. Cruise lines that had docked in Cuban cities after a half-century hiatus a few years earlier were sued for hundreds of millions of dollars in Florida courts.

The State Department returned the island, without evidence, to its list of state sponsors of terrorism. As Drop Site News has previously reported, this locked the island out of the world’s banking system.

These sanctions gored the island’s foreign earnings, which today are just a third of what they were in 2019, according to official figures. This has disproportionately damaged the lives of the most vulnerable: rice and beans today come late if at all; children receive less milk; infant mortality has risen as the budget for importing medicine has more than halved.

But to shatter Obama’s normalization, the administration went well beyond sanctions. According to a recent article by investigative journalist Zach Dorfman, paramilitary experts were consulted to work out how to sabotage Venezuelan oil deliveries to the island, which are vital for keeping the lights on. The C.I.A. was pressured to use a covert system to disable oil tankers shipping to Cuba. The C.I.A. reportedly stood up to the pressure, but one imagines that in his second term Trump will push US intelligence services even harder.

Trump also expelled Cuban diplomats from Washington and shuttered the newly reopened American embassy. This came after reports that two-dozen diplomats, family members, and intelligence officers fell ill. While the symptoms of headaches, dizziness and loss of balance seem to have been reported in good faith, the administration said these officials had been “attacked” by a sonic weapon. There was never any compelling evidence to support the attacks claim, but the Havana Syndrome narrative—hyped by hardliners and carried by credulous media—proved decisive in scuppering normalization. Last year an intensive review by U.S. intelligence agencies concluded there was no evidence attacks ever took place.

On the 2020 campaign trail, Biden made many pledges to engage in a progressive foreign policy that he never fulfilled. He said that the Trump policies “harmed” Cubans and that he would shift back towards the Obama policy. He never did. While the embassy was restaffed, flights were increased, and remittances were loosened, his administration kept the most powerful sanctions—the investment chilling Helms Burton Title III and the evidence-free state sponsor of terrorism label—in place.

How Biden Got Cuba So Wrong

From the get-go, the top brass in the Biden State Department saw the Cuba policy they inherited as a foreign policy failure. But after poor 2020 electoral performances in south Florida, the White House prevented them from acting, according to three Obama administration officials who spoke on condition of anonymity.

Fear of Florida simmered in Biden’s inner circle. Ron Klain, the White House chief of staff from 2020 to 2023, had been shaped by the Elián Gonzalez scandal of 2000, in which a seven-year-old boy was discovered in the Florida Straits and then repatriated to his father in Cuba. That year, Al Gore lost the state, and with it the presidency, by just 537 votes. Klain ran the Florida recount for the Democrats: “I’ll never be over it,” he has said.

The administration said it would listen to Cuban Americans before making policy. In practice, this meant ceding policy to hardliners, like Cuban American New Jersey Senator Bob Menendez. At the beginning of his political career in the ‘80s, Menendez had supported Omega 7, a Cuban American group, described by the FBI as America’s “most dangerous terrorist organization” because of its bombing and assassination campaigns in New Jersey and New York. This year, Menendez was forced to resign as chairman of the Senate Foreign Relations Committee after he was convicted of bribery, in which he accepted gold and cash for political favors.

Throughout Biden’s term, so-called democracy promotion programs (understood as regime change programs by the Cuban government) kept pumping about $20 million dollars of federal funds a year, usually through USAID, to organizations that try to shape Cuban politics.

In many countries USAID is fairly transparent about how money is spent. But Cuba is one of the few countries in the world where it operates not with the host government, but against it. Programs are effectively covert.

Back during secret negotiations in 2014 AP revealed that USAID had secretly been building a “Cuban Twitter” to organize “smart mobs” on the island, as well as infiltrating the island’s hip hop scene to spark unrest. But the Obama administration left these programs untouched. Over the last decade, the offices of senators like Menendez and Rubio, which hold sway over these programs, had money channeled to conservative organizations that opposed normalization. Dissident journalists, academics, musicians, and artists in Cuba got some of the funds too; many were harassed by the Cuban state.

In a recent publication, Armstrong, the former intelligence analyst, argues these programs “influence U.S.-based audiences, think tanks, and ultimately political deliberations.” Washington, he writes, “is awash in information about Cuba that itself has directed. The firewall between covert operations and policy is gone”

“The industry,” he said, “was crucial in keeping the Biden people in the pocket of the anti-normalization crowd.”

On July 11, 2021, the state cracked down on the unprecedented nationwide anti-government protests: hundreds of people received long prison sentences. By this point the state could barely afford fuel to keep the lights on, and protests started after a 12-hour power outage in a small westerly town, and spread spontaneously throughout the island, powered by now widely available mobile internet and amplified by thousands of off-island Twitter bots. An ugly crackdown ensued. The Biden administration would point to this as why moving on Cuba became politically impossible, but the decision had been made long before.

Almost nobody benefits from the current policy. It’s hard to see how even the U.S. national interest is advanced. The majority view of people who work on Latin America within the national security and intelligence agencies has long been that engagement is best for American interests (Drop Site News has seen a letter calling for more engagement sent to President Biden today by officials who led U.S. diplomacy in Havana, crafted Obama's Cuba policy in the White House, and determined terrorism designations at the State Department). The current policy has driven the island further into the orbit of adversaries Russia and China. This year a Russian submarine pulled into exactly the same place American cruise liners used to dock.

Democrats haven’t benefited either. The policy has driven a humanitarian crisis leading to historic migration out of the country. The population has reduced by more than a million since the pandemic, according to the Cuban government, with more than than 670,000 Cubans making it to the U.S., according to Customs and Border Protection. This played into the Republican’s hands by fueling the border crisis narrative. The Democrats ended up getting trounced in Florida last month, losing by a wider margin than in 2020 (two-thirds of Cuban Americans said they would vote for Trump, according to this year’s authoritative Florida International University poll). For the foreseeable future, Florida has shifted from a battleground to a red state.

The Trump-Biden policy has demonstrably undermined the human rights of the Cuban people.

The last eight years have made a mockery of Obama’s entreaty for Cuba to open up as it had “nothing to fear from the United States”—allowing hardliners in Havana to say, “We told you so” and making those who believed better relations with the U.S. were possible look naive. Today, according to human rights organizations, hundreds of Cubans are in jail for exercising their political and civil rights—perhaps an order of magnitude more than a decade ago.

What to Expect From Rubio

Last month’s presidential election and the choice of Marco Rubio as secretary of state was a double whammy for Cubans. But for hardliners in Washington it heightened feelings of triumphalism. Carlos Trujillo, ambassador to the Organization of American States during the first Trump administration and now on the Trump transition team and jostling for a post again, has bragged, “If you look at what happened in Cuba, the total collapse of their economy was caused by the pressure that President Trump implemented.”

Claver-Carone, who is also on the transition team, told the Miami Herald last month that “focus should be on modernizing Cuba sanctions so that they can have third-party effects.”

Experts agree sanctions can be ramped up the even further. For example, secondary sanctions could be implemented, in which the U.S. could sanction foreign companies for doing business in Cuba even when their business has no relation to the U.S. Hotels that run resorts in Cuba and the U.S. or airlines that fly to both countries could be put out of business unless they cease all business on the island.

But not everybody in the incoming administration has visceral feelings against the island. Trump himself may be the wildcard. On the campaign trail in 2015, the consummate wheeler-dealer whose foreign policy was governed more by the last person he spoke to than by principle, said “50 years is enough—the concept of opening with Cuba is fine. I think we should have made a stronger deal.” The Trump trademark had even been registered on the island in 2008 to develop hotels, casinos and golf courses.

His own team has expressed openness to the island. Sergio Gor, Trump’s incoming director of the Office of Personnel Management, holidayed in Cuba in June 2017, memorializing the trip in a series of Facebook posts.

If Cuban American hardliners do get to control policy towards the island, one area where it will jar with Trump pledges is migration. The sanctions have already driven the biggest wave of Cubans to the U.S.’s southern border in history. More sanctions continue this trend. It’s unlikely Cuba will accept mass deportations. Cuban Deputy Foreign Minister Fernando de Cossio said earlier this month that plans to deport tens of thousands of Cubans living illegally to the U.S. were “unrealistic” and “unfair.” It remains to be seen whether the drive to reduce migration or the drive to further hammer the island will win out. Marco Rubio will have far bigger issues to deal with and by radically shifting his position on Ukraine he has shown he is willing to volte face.

For Hal Klepak, professor emeritus of history and strategy at the Royal Military College of Canada and Cuba expert, the situation on the island today is “exactly the opposite” of the palpable joy and belief that things could get better a decade ago. “People are quite literally hopeless and see no possibility of light at the end of the tunnel,” he said. The current situation “stimulates a lethargy and an unwillingness to do anything other than flee.”