INTREP360 INTELLIGENCE REPORT

05.14.2026

May 14^th, 2026

Greetings!

I am going to carbon date myself; however, as a child of the 1960s, it cannot be helped. For me, at least, growing up in the 1960s was framed by the Cuban Missile Crisis, President John F. Kennedy & Martin Luther King Jr.’s assassinations, the ever-deepening war in Vietnam & the space race to the moon.

AI image credit: Grok. Graphic depicting the Cuban Revolution potentially coming to an end.

Yet, before the October 1962 showdown between Kennedy and Nikita Khrushchev, the then leader of the Soviet Union, there was the Bay of Pigs.

It was, simply put, an American disaster. Indeed, the Central Intelligence Agency (CIA) became essentially synonymous with it. Effectively, the plan to overthrow then Cuban President Fidel Castro failed at every level.

Plus, it took decades for the CIA to recover.

Fast-forward to today.

That’s why it was jarring for me to learn earlier today that John Ratcliffe, the director of the CIA, was in Havana to meet with Cuban government officials. The ghosts of my youth came crashing back in a sudden flash.

Cuba is on the brink of economic, if not domestic collapse.

Let’s get started understanding why and how this childhood nightmare story may soon have a happier ending for the long-repressed people of Cuba.

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THE ISLAND THAT TIME FORGOT

Cuba, in many ways, is the island that time forgot. Since the Cuban Revolution led by Castro on January 1^st, 1959, that overthrew the government of pro-U.S. Fulgencio Batista, the Caribbean country has been caught in a time warp.

Visually, much of the island appears as it did in the 1950s. “Yank tanks,” as vintage American cars are known, are the most symbolic.

Photo credit: Ottocrank / Threads. Photograph of “Yank tanks” parked in a Havana, Cuba public square, dated December 13^th, 2024.

Yet the classic cars are merely symptomatic. The country’s woes run much deeper than that. It is Cuba’s economy that has largely been in a cryogenic state for 67 plus years.

In 1958, one year out from Castro’s revolution, Cuba trailed only Venezuela and Uruguay on a gross domestic product (GDP) basis. That was nearly 60% of Europe’s GDP which was still recovering from World War II; and it was nearly 30% of U.S. GDP.

Auto ownership was at 24 cars per 1,000 inhabitants or the second highest in all of Latin America and only behind Venezuela. TV ownership — while an afterthought today, it was huge back then as a newly emerging communications technology — was the fifth highest in the world on a per capita basis.

In 1957, TIME Magazine, while reporting on a Castro-led nationwide strike, noted that Cuba’s national income was “estimated at a record $2.2 billion.” Cuba’s economy was booming and it was led by $612 million of industrial investment — $70 million of that from the U.S. — and $35 million from 350,000 tourists.

Then, after the Cuban Revolution two years later, the country’s economy flatlined and it has never fully recovered since. Between 1959 and 2006, Cuba’s per capita growth on an annualized basis averaged only 0.92%. Latin America — where it had once been a dominant economy — averaged 1.67% GDP growth during that same time period.

Cuba’s economy is still trailing until this day. According to Trading Economics, its GDP per capita, based on the latest available data in 2024, “is equivalent to [only] 58 percent of the world’s average.”

Notably, the latest figures are prior to Cuba’s present economic collapse under severe economic pressure by the Trump Administration.

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HAVANA NIGHTS

Pre-revolutionary Cuba wasn’t Nirvana. Batista was a U.S.-backed dictator and he repeatedly “organized repression of anyone with left-wing sympathies, especially students, and trade unionists involved in Cuba’s lucrative sugar production.”

Batista, in a move that would be mirrored by Vladimir Putin a half a century later in Russia, found his “soulmate” in the Mafia. While Batista married the mob courtesy of a military coup in 1952, Putin married the mob in St. Petersburg via the Federal Security Service (the primary successor to the KGB).

Santo Trafficante Jr., Meyer Lansky, and Charles “Lucky” Luciano were three of the major American Mafia figures operating in Cuba. Trafficante, notoriously, “was involved with the CIA in a number of attempts to assassinate Fidel Castro.”

Lansky was the king of drug trafficking & prostitution. Luciano was heavily involved in Cuba’s casinos.

U.S. movie & recording celebrities, including Frank Sinatra, Errol Flynn, Nat King Cole, George Raft & many others lit up those Havana nights, especially in the city’s casinos. Fittingly, one of their fellow stars was Marlon Brando, who would later play the ultimate movie godfather in an Academy Award winning role.

Photo credit: Ralph Morse / LIFE. Tourists and Cubans gamble at the casino in the Hotel Nacional in Havana, 1957. Meyer Lansky, who led the U.S. mob’s exploitation of Cuba in the 1950s, set up a famous meeting of crime bosses at the hotel in 1946.

The good life — despite the high GDP in the 1950s — had a dark side and Hollywood glam didn’t stop Castro from toppling it. Yet, in turning off those Tinseltown lights, Castro and his communist cronies effectively turned off Cuba as well.

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COLD WAR, DARK TIMES

Cuba, during the Cold War, traded mob life for Soviet life. It fended off the likes of Trafficante, Lansky & Luciano, but it plunged the country into the economic abyss.

Castro — who was furious for a while with Khrushchev after Moscow pulled its nukes in October 1962 in a deal with Kennedy — eventually married his economy to that of the Soviet Union. This included joining the Council for Mutual Economic Assistance in July 1972, which fully implemented Cuba’s economy into the communist bloc.

It wasn’t a good move.

The country quickly became dependent on massive Russian subsidies — eventually upwards of $4 billion per year — to obtain cheap oil, machinery, and military aid in exchange for exporting sugar at premium prices. Literacy, healthcare & education improved — all good things — however Cuba thereafter faced chronic shortages, rationing & political repression.

Free stuff usually comes at the expense of free will. Cuba, under Castro, found that maxim out the hard way.

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EXPORTING REVOLUTION

By the 1970s Cuba –– as a key ally of the Soviet Union during the Cold War –– began exporting its revolution. Initially, it began in Angola as part of Operation Carlota wherein between 1975 to 1991, Cuba sent hundreds of thousands of troops to back the People’s Movement for the Liberation of Angola (MPLA) during the country’s civil war.

It didn’t stop there. Cuba also intervened in Ethiopia in 1977 & supported various communist movements in Africa & Latin America, including Guinea-Bissau, Mozambique (many older Cold War era readers might remember FRELIMO), Democratic Republic of Congo, Bolivia, Nicaragua & El Salvador.

Nor would it stop there. Eventually, Cuba — as part of the Axis of Evil — would begin partnering with Venezuela.

Plus, it would come with a twist of irony. Venezuela was — and still is — ruled by cartels, the modern-day cousins once removed of the Mafia.

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ENTER VENEZUELA

Cuba was reeling after the fall of the Soviet Union in 1991. While Havana & Moscow stayed aligned, Castro needed new allies.

That opportunity came in 1999, beginning with the rise of Hugo Chávez, the former Venezuelan president. Castro immediately began cultivating close economic & cultural ties with Chávez & one year later entered into the Convenio Integral de Cooperación agreement — which at the time, was known as the “oil for doctors” barter deal between Havana & Caracas.

Photo credit: Adalberto Roque / AFP. Venezuela’s then-president-elect Hugo Chavez, flanked by then-Cuban leader Fidel Castro at the Jose Marti airport in Havana in 1999.

Venezuela started shipping upwards of 100,000 barrels of oil per day to Cuba and, in return, Havana sent tens of thousands of Cuban doctors, teachers, sports coaches, technical experts, & military advisers.

Eventually, it grew over time after now ousted Venezuelan President Nicolás Maduro succeeded Chavez after his death. That included Cuba sending upwards of 50,000 security agents to serve as Maduro’s bodyguard.

Operation Absolute Resolve put an end to that in January.

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TRUMP TURNS OFF THE LIGHTS

One of President Donald Trump’s first actions after interdicting Maduro was to cut off Venezuelan oil shipments to Cuba. He also issued an executive order on January 29^th threatening tariffs on any country supplying Havana with oil.

Consequently, Cuba is fast running out of diesel & fuel oil which has led to rolling blackouts of 20 plus hours a day. Simply put, Cuba is going dark & its national power grid is on the verge of complete collapse.

Photo credit: Ernesto Mastrascusa / EPA-EFE. Havana, Cuba under a blackout in a recent photograph.

Weaponizing energy against civilians is never a good thing. Certainly, Jon & I have condemned Russia for doing just that when Jon took the lead for us writing in The Hill about Putin’s strategy to weaponize winter.

Trump, for the sake of innocent civilians, has to find an end game in Havana. Hopefully, Ratcliffe’s trip to Cuba results in just that.

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OUR MAN IN HAVANA

Ratcliffe is Washington’s latest man in Havana. It was likely not coincidental that he was in Cuba while Trump was in Beijing meeting with Chinese President Xi Jinping at the same time. It was messaging squarely aimed at the Axis of Evil: the Western hemisphere is off limits to China, Russia, Iran & North Korea.

Photo credit: CIA. CIA Director John Ratcliffe (left) leads a U.S. delegation to Havana to meet with Cuban government officials on May 14^th, 2026.

The CIA director — of course — also had a message for Cuba. It’s time to pick a side & there is really only one choice Havana can make.

Tough? Yes. Fair? No.

But in reality, Cuba doesn’t have much of a choice. Ratcliffe’s meeting today with Interior Minister Lázaro Álvarez Casas & Raúl Guillermo “Raulito” Rodríguez Castro — the grandson of Raúl Castro, the de facto leader of Cuba & surviving brother of Fidel Castro — was likely take-it-or-leave it deal.

Either the regime makes fundamental changes — including pivoting away from the Axis of Evil — or the lights stay out.

Let’s hope the lights come on. It’s high time that the geoglobal ghosts of my 1960s youth, including the Bay of Pigs ghosts that the CIA hopes to finally exorcise, are finally put to rest.

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ICYMI

Earlier today, our weekly Thursday national security column at The Hill in Washington, D.C. focused on Iran’s efforts to hijack Trump’s state visit to China.

Photo credit: Mark Schiefelbein / AP. President Donald Trump (left) is greeted by Chinese Vice President Han Zheng in Beijing on May 13^th, 2026.

You can read it here.

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Thank you for reading. We will see you tomorrow. Please subscribe, comment & share. We truly appreciate it!

Mark

Follow Jon on X at @JESweet2022 or on Bluesky at @JonSweet.bsky.social. Follow Mark on X at @MCTothSTL or on Bluesky at @MarkToth.bsky.social.