Cubastroika: Inside Trump plan to save Cuba's economy and win control
Cubastroika: Inside Trump plan to save Cuba's economy and win control
Rick Jervis and Francesca Chambers, USA TODAYSat, March 7, 2026 at 10:05 AM UTC
0
Aldo Álvarez’s vans sat idle for three weeks, baking in the Cuban sun.
There was no fuel to be found in the capital for his delivery company’s fleet of 10 trucks and vans.
Power outages ran 15 hours a day. Airlines canceled flights due to inability to refuel. Hotels were shuttered. Classes canceled. Tourism dried up.
After the dramatic capture of Nicolás Maduro in Venezuela by U.S. special forces on Jan. 3., President Donald Trump shut off the flow of oil to Cuba. An island of 10 million people plunged into darkness.
Cuba appeared to be the Trump administration’s next target for regime change – one that would realize the dreams of Cuban exiles and many Republicans for a U.S.-backed blow that would end the enduring communist regime.
But the administration’s aim for the island nation seems to be a more subtle one, despite calls from the White House for Cuba to “make very dramatic changes very soon.”
Trump, in lockstep with his Secretary of State and longtime Cuba hawk, Marco Rubio, is rolling out moves designed to make Cuba dependent on the U.S. economy – a striking about-face from decades of U.S. policy toward Cuba.
On Feb. 25, the Trump administration began allowing U.S. petroleum products, such as diesel, to be sold directly to Cuba’s private sector, circumventing the longstanding 1960 U.S. embargo.
And hoping business owners like Álvarez can play a key role.
Álvarez was buoyed recently with news that U.S. companies would be exporting diesel directly to Cuba’s small businesses – something that hadn’t been done in more than six decades. Fuel reached the nearby gas station.
The vans revved back up.
“It’s transformative,” Álvarez, founder of Mercatoria, told USA TODAY from Havana. “I can guarantee my [fuel] supply in a stable way … Without a doubt, it’s good news.”
Though Trump hasn’t hesitated to use military force in places like Venezuela and Iran, bringing change to Cuba’s repressive regime may be more akin to a slow, steady economic dependence on U.S. products – a Caribbean-style perestroika, or the gradual granting of market-like reforms that led to the eventual collapse of the Soviet Union.
A woman walks on the street as Cuba brought its national electrical grid back online after the country had been largely without power for 16 hours in an outage that Energy Ministry officials linked to the oil blockade of Cuba imposed by the United States, in Havana, Cuba, March 5, 2026. REUTERS/Norlys Perez
More: Why did US launch military operations in Ecuador? Here's what we know
‘A friendly takeover of Cuba’
The shift in approach is huge.
“You have the Trump administration recognizing the Cuban private sector as both a real sector and also a key strategic partner on the ground to help relieve the humanitarian crisis," said Ric Herrero, executive director of the Cuba Study Group, a Washington-based non-profit policy and advocacy group. “We’ve never seen that before."
Reports also surfaced that Rubio and his aides had back-channel talks with the grandson of Cuba’s aging dictator, Raul Castro.
Trump confirmed on Feb. 27 Rubio was talking with Cuban officials “at a very high level” and warned that Cuba is a weakened state. “Maybe we'll have a friendly takeover of Cuba," he mused to reporters.
On March 6, the president reiterated his focus on Cuba, telling CNN the communist island "is gonna fall pretty soon." Federal prosecutors are also looking into potentially charging members of Cuba's regime or communist party with crimes, as they did with Maduro before his ouster, according to NBC News.
Trump and Rubio will confer with like-minded Latin American leaders from countries such as Argentina and El Salvador at a March 7 summit at the president's Doral golf club, where Cuba is expected to be part of the discussion.
Trump eyes Cuba: As U.S. pressures Cuba, Trump says there could be 'friendly takeover'
A vintage car is parked outside the Provincial Clinical–Surgical Hospital "Arnaldo Milian Castro," where, according to local information, injured people on Feb. 26, 2026, were being treated after an armed incident involving a Florida-registered speedboat and a Cuban patrol vessel.
Then, the high-seas shootout.
The murky gunfight last week between a boat full of Cuban-Americans and the Cuban coast guard near Cuba’s northern coast last week ended in the killing of four people on the boat – including at least one U.S. citizen – and the injury and capture of six others. The incident made headlines and hatched online conspiracies as to the gunmen’s motives but is not expected to alter U.S. strategy toward Cuba.
It’s unclear how U.S. officials plan to use direct economic contact with Cuba’s private sector as a means to foment change. At a Feb. 25 summit at St. Kitts and Nevis, Rubio reiterated that U.S. officials are not expecting abrupt change in Cuba.
“The status quo is unacceptable … Cuba needs to change,” he told reporters. “It doesn’t have to change all at once. It doesn’t have to change from one day to the next … But Cuba needs to change. It needs to change dramatically.”
High-seas shootout: Florida boat in Cuban high-seas shootout stolen, US citizens aboard
Eric Jacobstein, former deputy assistant secretary of state for western hemisphere affairs in the Biden administration, traveled to the island repeatedly to meet with Cuban entrepreneurs and encourage them to connect with U.S. businesses.
For Trump’s strategy to take root, Cuba’s private sector will need increased help from American businesses, particularly the banking sector, he said.
“It's critical to engage this independent Cuban private sector,” Jacobstein said. “They're independent, they're entrepreneurial … It's a group that has embraced capitalism within a failing communist system.”
The Obama opening
Ever since Fidel Castro stormed Havana with his battalion of barbudos in 1959 and later announced the country’s allegiance to communism, American presidents have sought to coerce, constrain and even kill Cuban leadership. A U.S. embargo placed in 1960 barred most U.S. companies from doing business in Cuba.
Advertisement
Mar 21, 2016; Havana, Cuba; President Barack Obama listens to questions alongside journalist and small business owner Soledad O'Brien (left) during a business summit in Havana. Mandatory Credit: Jack Gruber-USA TODAY NETWORK
Starting in 2014, former President Barack Obama launched attempts at normalizing relations with Cuba, encouraging U.S-Cuban business ventures and even re-opening the U.S. embassy in Havana. In a historic visit to Cuba – the first for a sitting U.S. president since Calvin Coolidge 90 years earlier – Obama met with activists and entrepreneurs, bolstering the island’s fledgling private sector.
But those efforts were mostly superficial because they were not conditioned on anything, said John Kavulich, president of the U.S.-Cuba Trade and Economic Council, a trade group that has been dealing with Cuba since 1994.
A few U.S. businesses sought ventures on the island under Obama and cruise ships and airlines began ferrying travelers there. But the Cuban government mostly refused to reform the island’s stagnant economic system or allow direct foreign investment, he said.
Trump’s strategy is different in that it includes coercion and comes at a time when Cuba is struggling to survive, Kavulich said.
“The Cuban government does not have the elasticity to be able to play games as they did with President Obama,” he said.
1 / 0From Cuba to Panama: US interventions that shaped Latin America
This file photo shows a group of U.S. sailors from the battleship Connecticut and a gun they captured at Cape Haitien during the U.S. occupation of Haiti in 1915.
‘Everyone’s deathly afraid’
A key question is how the Cuban exile community in Miami and elsewhere will react to the U.S. having such direct contact with officials and entrepreneurs on the island – something they’ve strongly opposed for years, said Michael Bustamante of the Cuban and Cuban-American Studies at the University of Miami.
The recent interaction between Rubio, who as a U.S. senator strongly criticized Obama’s overtures to Cuba, and Raul Castro’s grandson was a jarring turn of events, he said.
“I think it’s a surprise to many folks,” Bustamante said. “Maybe it’s a surprise to him.”
More on Rubio: Marco Rubio, who dreamed of ousting Venezuela’s Maduro, takes charge
As the U.S. Cuba strategy emerged, Kavulich said his council was contacted by members of the Trump administration, asking if any executives would be willing to publicly support the president’s strategy of dealing directly with Cuba’s private sector. They suggested forming a “CEO Council for Free and Democratic Cuba,” or something akin.
Kavulich polled his members. None would agree.
“Everyone's deathly afraid that the administration will be supportive in the morning and by lunchtime will be criticizing them,” Kavulich said. “So, they're just taking a ‘wait-and-see’ attitude.”
People buy food in a shop in Havana, Cuba, July 22, 2025. REUTERS/Norlys Perez
He said the strategy emerging from the White House is less perestroika and more bankruptcy filing.
“They're not liquidating, they're reorganizing,” Kavulich said of the Cuban government. “We're going to continue to see a government version of Chapter 11 reorganization.”
11,000 Cuban businesses ready to flourish
Cuban officials – their main supply of oil pinched off, images of a cuffed and blindfolded Maduro inside a U.S. assault ship just a few weeks old – so far seem to be paying attention.
At a meeting of high-ranking officials in Havana this week, Cuban President Miguel Diaz-Canel stressed the importance of “implementing the most urgent and necessary transformations to the economic and social model,” according to Granma, Cuba’s communist party newspaper – a stark reversal from a communist island historically averse to economic reform.
He added that the initiatives "are fundamentally related to business autonomy; municipal autonomy … leveraging economic partnerships between the state and private sectors, especially at the municipal level; and promoting business with Cubans residing abroad."
Cuban officials like Diaz-Canel have promised reform before without delivering, but this time Trump’s bellicose coercion and the growing crisis on the island could force them to actually act, Kavulich said.
There are an estimated 11,000 small- to medium-sized independent businesses in Cuba, many of them centered around Havana, from restaurants in homes known as paladares to online delivery services.
“It was easy to see President Trump was not going to focus on removing communism from Cuba as much as he was going to focus on commercial, economic, financial engagement first,” Kavulich said. “I don't think anyone should be surprised if we eventually see [special U.S. envoy] Steve Witkoff and [Trump advisor] Jared Kushner in Havana negotiating with the Cuban government.”
Robert Muse, a Washington attorney who specializes in helping U.S. businesses in Cuba, said most business leaders are still cautiously watching events unfold.
For years, many waited for Cuba to evolve into a Vietnam or China – a country that retained its communist ideology but opened its economy to allow trade and foreign investment, he said. But that never happened, despite pressure from China and Russia, two of Cuba’s biggest benefactors.
The fading embers of a revolution
Now, most vestiges from the 1959 Cuban revolution are fading or dead. Fidel Castro died in 2016 and his brother, Raul Castro, the island’s de facto dictator, and Ramiro Valdés, former vice-prime minister and close confidant of the Castros, are both in their 90s.
That, along with a suffering population and the oil embargo, creates an ideal opportunity for the Trump administration to spark meaningful change on the island, Muse said. Doing it through the private sector was a wise move, he said.
“There's a slowly emerging consciousness that this is the year of decision” in Cuba, Muse said. “This is elemental economic reform in Cuba.”
Álvarez, the Havana-based entrepreneur, said he recognizes the weight of the moment and the rarity of receiving U.S. fuel directly from U.S. companies.
He said the situation in Cuba has been dire, with many companies dormant due to the oil crisis and people struggling to get by.
But he feels Cuba is entering a period of reform – and business owners such as himself are at the forefront.
“They’ve given us a huge responsibility,” Álvarez said. “And the private sector will meet that responsibility.”
Follow Jervis on X: @MrRJervis.
This article originally appeared on USA TODAY: Inside Trump's plan to win Cuba with American oil
Source: “AOL Breaking”
