By Dennis Hartley
(Originally posted on Digby’s Hullabaloo on March 7, 2026)
There’s just something about (Castro’s) Cuba that affects (U.S. presidential) administrations like the full moon affects a werewolf. There’s no real logic at work here.
-an interviewee from the documentary 638 Ways to Kill Castro
If I could only live to see it, to be there with you. What I wouldn’t give for twenty more years! Here we are, protected, free to make our profits without Kefauver, the goddamn Justice Department and the F.B.I. ninety miles away, in partnership with a friendly government. Ninety miles! It’s nothing! Just one small step, looking for a man who wants to be President of the United States, and having the cash to make it possible. Michael, we’re bigger than U.S. Steel. – From The Godfather, Pt. II, screenplay by Francis Ford Coppola and Mario Puzo
Which reminds me of a funny story…
Trump: "We're looking forward to the great change that will soon be coming to Cuba. Cuba is at the end of the line. They're very much at the end of the line."
“End of the line”? Would you care to…elaborate on that, Mr. Preznit?
Trump: "Cuba is in its last moments of life … but our focus right now is on Iran. Marco will take one hour off and finish up a deal on Cuba. That'll be an easy one."
Kinda like one-hour Martinizing? Bish, bash,bosh?
During his second term, President Donald Trump has authorized military action in a string of countries, including Iran, Venezuela, Ecuador, Nigeria, Somalia, and Yemen. Now, he’s hinted that Cuba could be next, declaring that the Caribbean island nation is “in its last moments of life.”
Trump delivered his stark warning during a Saturday speech in Florida, where leaders from several Latin American nations were gathered at his Doral resort.
There, he unveiled a new coalition called “The Shield of the Americas,” aimed at bolstering security across the Western Hemisphere. Kristi Noem has been tapped as a special envoy for the initiative, following her dismissal as Homeland Security secretary.
Upon taking the podium, the president said he is “looking forward to the great change that will soon be coming to Cuba.” He described the nation as “at the end of the line” and experiencing its “last moments of life.”
The country, which has been under communist rule since the 1959 Cuban revolution, has no money, no oil, and a “bad philosophy,” he continued.
While his administration is currently focused on Iran, Trump said that Secretary of State Marco Rubio will “take one hour off and finish up a deal on Cuba,” adding, “That’ll be an easy one.”
Since returning to office, Trump has taken an aggressive posture towards Cuba. He’s slapped steep tariffs on the island nation and threatened to impose duties on goods from countries that export oil to Cuba. He’s also urged the communist state to “make a deal” or face unspecified repercussions.
The country’s president, Miguel Diaz-Canel, has frequently criticized the Trump administration’s hostile rhetoric.
“Cuba is a free, independent and sovereign nation. No one tells us what to do,” he wrote on X in January, adding that his government was “ready to defend the homeland to the last drop of blood.”
For all you youngsters in the audience, the cigar-chomping dictator who once inspired a documentary entitled 638 Ways to Kill Castro (more on that below) was finally taken out in 2016 by method #639: Old age. Regardless of who is in charge of the island nation now, it’s been a long, strange trip for U.S.-Cuban relations since Castro seized power in 1959.
But I’m sure Secretary Rubio will get it straightened out in an hour or so.
While we’re holding our breath, here are 10 Cuba-themed films worth a peek:
Bananas– Yes, I know. This 1971 Woody Allen film takes place in the fictional banana republic of “San Marcos”, but the mise en scene is an obvious stand-in for Cuba. There are also numerous allusions to the Cuban revolution, not the least of which is the ridiculously fake beard donned at one point by hapless New Yawker Fielding Mellish (Allen) after he finds himself swept up in Third World revolutionary politics. Naturally, it all starts with Allen’s moon-eyed desire for a woman completely out of his league, an attractive activist (Louise Lasser). The whole setup is utterly absurd…and an absolute riot. This is pure comic genius at work. Howard Cosell’s (straight-faced) contribution is priceless. Allen co-wrote with his Take the Money and Run collaborator, Mickey Rose.
Buena Vista Social Club- This engaging 1999 music documentary was the brainchild of musician Ry Cooder, director Wim Wenders, and the film’s music producer Nick Gold. Guitarist/world music aficionado Cooder coaxes a number of venerable Cuban players out of retirement (most of whom had their careers rudely interrupted by the Revolution and its aftermath) to cut a collaborative album, and Wenders is there to capture what ensues (as well as ever-cinematic Havana) in his inimitable style. He weaves in footage of some of the artists as they make their belated return to the stage, playing to enthusiastic fans in Europe and the U.S.
Che– Let’s get this out of the way. Ernesto “Che” Guevara was no martyr. By the time he was captured and executed by CIA-directed Bolivian Special Forces in 1967, he had put his own fair share of people up against the wall in the name of the Revolution. Some historians have called him “Castro’s brain”.
That said, there is no denying that he was a complex, undeniably charismatic and fascinating individual. By no means your average revolutionary guerrilla leader, he was well-educated, a physician, a prolific writer (from speeches and essays on politics and social theory to articles, books and poetry), a shrewd diplomat and had a formidable intellect. He was also a brilliant military tactician.
Steven Soderbergh and his screenwriters (Peter Buchman and Benjamin A. Van Der Veen) adapted their 4 ½ hour opus from Guevara’s autobiographical accounts. Whereas Part 1 (aka The Argentine) is a fairly straightforward biopic, Part 2 (aka Guerilla) reminded me of two fictional films with an existential bent, both also set in torpid South American locales-Clouzot’s The Wages of Fear and Herzog’s Aguirre, the Wrath of God. Like the doomed protagonists in those films, Guevara is fully committed to his journey into the heart of darkness, and has no choice but to cast his fate to the wind and let it all play out. Benicio del Toro shines in the lead role. Full review
The Godfather, Part II– While Cuba may not be the primary setting for Francis Ford Coppola’s superb 1974 sequel to The Godfather, it is the location for a key section of the narrative where powerful mob boss Michael Corleone (Al Pacino) travels to pre-Castro Havana to consider a possible business investment. He has second thoughts after witnessing a disturbing incident involving an anti-Batista rebel. And don’t forget that the infamous “kiss of death” scene takes place at Batista’s opulent New Year’s Eve party…just as the guests learn Castro and his merry band of revolutionaries have reached the outskirts of the city and are duly informed by their host…that they are on their own! And remember, if you want to order a banana daiquiri in Spanish, it’s “banana daiquiri”.
Harold and Kumar Escape from Guantanamo Bay– Picking up where they left off in their surprise stoner comedy hit Harold and Kumar Go to White Castle, roomies Harold (John Cho) and Kumar (Kal Penn) excitedly pack their bags for a dream European vacation in weed-friendly Amsterdam. Unbeknownst to Harold, Kumar has smuggled his new invention, a “smokeless” bong, on board.
When a “vigilant” passenger, already eyeballing Kumar with suspicion due to his ethnic appearance, catches a glimpse of him attempting to fire up his homemade contraption in the bathroom, all hell breaks loose. Before they know it, Harold and Kumar have been handcuffed by on-board air marshals, given the third degree back on the ground by a jingoistic government spook and issued orange jumpsuits, courtesy of the Gitmo quartermaster.
Through circumstances that could only occur in Harold and Kumar’s resin-encrusted alternate universe, they break out of Cuba, and hitch a boat ride to Florida. This sets off a series of cross-country misadventures. As in the first film, the more ridiculously over-the-top their predicament, the funnier it gets. It’s crass, even vulgar; but it’s somehow endearingly crass and vulgar, in a South Park kind of way (i.e. the goofiness is embedded with sharp political barbs). (Full review)
I Am Cuba – There is a tendency to dismiss this 1964 film about the Cuban revolution as Communist propaganda. Granted, it was produced with the full blessing of Castro’s regime, who partnered with the Soviet government to provide the funding for director Mikhail Kalatozov’s sprawling epic. Despite the dubious backers, the director was given a surprising amount of creative freedom.
On the surface, Kalatozov’s film is in point of fact a propagandist polemic; the narrative is divided into a quartet of rhetoric-infused vignettes about exploited workers, dirt-poor farmers, student activists, and rebel guerrilla fighters.
However it is also happens to be a visually intoxicating masterpiece that, despite accolades from critics over the decades, remains relatively obscure. The real stars of the film are the director and his technical crew, who will leave you pondering how they produced some of those jaw-dropping set pieces and logic-defying tracking shots.
The Mambo Kings– Arme Glimcher’s underrated 1992 melodrama concerns two musician brothers (Armand Assante and Antonio Banderas) who flee Cuba in the mid-1950s to seek fame and fortune in America. Hugely entertaining, with fiery performances by the two leads, great support from Cathy Moriarty and Maruschka Detmers, topped off by a fabulous soundtrack. Tito Puente gives a rousing cameo performance, and in a bit of stunt casting Desi Arnaz, Jr. is on hand to play (wait for it) Desi Arnaz, Sr. (who helps the brothers get their career going). Cynthia Cidre adapted her screenplay from Oscar Hijuelos’ novel.
Our Man in Havana– A decade after their collaboration on the 1949 classic, The Third Man, director Carol Reed and writer Graham Greene reunited for this wonderfully droll 1960 screen adaptation of Greene’s seriocomic novel. Alec Guinness gives one of his more memorable performances as an English vacuum cleaner shop owner living in pre-revolution Havana. Strapped for cash, he accepts an offer from Her Majesty’s government to do a little moonlighting for the British Secret Service. Finding himself with nothing to report, he starts making things up so he can stay on the payroll. Naturally, this gets him into a pickle as he keeps digging himself into a deeper hole. Reed filmed on location, which provides an interesting snapshot of Havana on the cusp of the Castro era.
Scarface (1983)– Make way for the bad guy. Bad guy comin’ through. Tony Montana (Al Pacino) is a bad, bad, bad, bad man, a Cuban immigrant who comes to America as part of the 1980 Mariel boat lift. A self-proclaimed “political refugee”, Tony, like the millions of immigrants before him who made this country great, aims to secure his piece of the American Dream. However, he’s a bit impatient. He espies a lucrative shortcut via Miami’s thriving cocaine trade, which he proves very adept at (because he’s very ruthless). Everything about this film is waaay over the top; Pacino’s performance, Brian De Palma’s direction, Oliver Stone’s screenplay, the mountains of coke and the carnage. Yet…it remains a guilty pleasure.
638 Ways to Kill Castro- History buffs (and conspiracy-a-go-go enthusiasts) will definitely want a peek at British director Dolan Cannell’s documentary. Mixing archival footage with talking heads (including a surprising number of would-be assassins), Cannell highlights some of the attempts by the U.S. government to knock off Fidel over the years. The number (638) of “ways” is derived from a list compiled by former members of Castro’s security team.
Although Cannell initially plays for laughs (many of the schemes sound like they were hatched by Wile E. Coyote) the tone becomes more sobering. The most chilling revelation concerns the 1976 downing of a commercial Cuban airliner off Barbados (73 people killed). One of the alleged masterminds was Orlando Bosch, an anti-Castro Cuban exile living in Florida (he had participated in CIA-backed actions in the past).
When Bosch was threatened with deportation in the late 80s, many Republicans rallied to have him pardoned, including Florida congresswoman Ileana Ros-Lehtinen, who used her involvement with the “Free Orlando Bosch” campaign as part of her running platform. Her campaign manager was a young up and coming politician named (wait for it) Jeb Bush. Long story short? Jeb’s Pappy then-president George Bush Sr. granted Bosch a pardon in 1990. Oh, what a tangled web, Jeb! BTW, Bosch was publicly referred to as an “unrepentant terrorist” by Richard Thornburgh, President Bush the First’s Attorney General. (Full review)
UPDATE: I dug up this pic froma 2011 post on then-Senator Rubio’s Facebook account :
“Sen. Marco Rubio, with Rep. Ileana Ros-Lehtinen, addressing the Bay of Pigs veterans.”
A tangled web, indeed.
Here are a few more recommendations:
Memories of Underdevelopment
Honey for Oshun
Chico and Rita
The Perez Family
Popi
