Intensifying efforts by President Donald Trump’s administration to end 67 years of communist rule in Cuba are drawing fierce criticism from many congressional Democrats. But not all.
Since Fidel Castro seized power in the 1959 Cuban revolution, the country has been a preeminent cause célèbre for the global Left. In this view, the island nation of about 10 million people, 90 miles from Key West, Florida, stands as a symbolic and physical focal point for anti-imperialism. Throw in decadeslong rhetoric about socialist experimentation and Third World solidarity, and Cuba, in the view of left-wing supporters, becomes a Western Hemisphere blunt-point political weapon to counter American hegemonic ambitions.
A common leftist critique lauds “universal healthcare” for Cubans provided by the Castro regime. Yet, this praise for Cuba’s social welfare state ignores its condition as an authoritarian one-party state under the Cuban Communist Party. A Cold War-era remnant where authorities systematically suppress dissent, restrict fundamental freedoms, and commit widespread human rights abuses.
Left: Rep. Pramila Jayapal (D-WA) and Rep. Jonathan Jackson (D-IL) pose for photojournalists at the Malecon in Havana on April 4. State Secretary Marco Rubio strongly opposed the Democrats’ outreach to Cuba. Right: From left to right: Cuban President Miguel Díaz-Canel, Raúl Guillermo Rodríguez Castro, and his grandfather, former Cuban President Raúl Castro (Photos by Ramon Espinosa/AP)
" data-large-file="https://www.washingtonexaminer.com/wp-content/uploads/2026/10/WB.WhiteHouse2.102126.jpg?w=696" height="658" width="1024" src="https://www.washingtonexaminer.com/wp-content/uploads/2026/10/WB.WhiteHouse2.102126.jpg?w=696" alt="Left: Rep. Pramila Jayapal (D-WA) and Rep. Jonathan Jackson (D-IL) pose for photojournalists at the Malecon in Havana on April 4. State Secretary Marco Rubio strongly opposed the Democrats’ outreach to Cuba. Right: From left to right: Cuban President Miguel Díaz-Canel, Raúl Guillermo Rodríguez Castro, and his grandfather, former Cuban President Raúl Castro (Photos by Ramon Espinosa/AP)" class="wp-image-4768467" style="width:318px;height:auto" srcset="https://www.washingtonexaminer.com/wp-content/uploads/2026/10/WB.WhiteHouse2.102126.jpg 1400w, https://www.washingtonexaminer.com/...6/10/WB.WhiteHouse2.102126.jpg?resize=300,193 300w, https://www.washingtonexaminer.com/...6/10/WB.WhiteHouse2.102126.jpg?resize=768,494 768w, https://www.washingtonexaminer.com/.../10/WB.WhiteHouse2.102126.jpg?resize=1024,658 1024w, https://www.washingtonexaminer.com/...26/10/WB.WhiteHouse2.102126.jpg?resize=150,96 150w, https://www.washingtonexaminer.com/...6/10/WB.WhiteHouse2.102126.jpg?resize=696,447 696w, https://www.washingtonexaminer.com/.../10/WB.WhiteHouse2.102126.jpg?resize=1068,687 1068w" sizes="auto, (max-width: 1024px) 100vw, 1024px">
Left: Rep. Pramila Jayapal (D-WA) and Rep. Jonathan Jackson (D-IL) pose for photojournalists at the Malecon in Havana on April 4. State Secretary Marco Rubio strongly opposed the Democrats’ outreach to Cuba. Right: From left to right: Cuban President Miguel Díaz-Canel, Raúl Guillermo Rodríguez Castro, and his grandfather, former Cuban President Raúl Castro (Photos by Ramon Espinosa/AP)
It’s been that way since late in President Dwight D. Eisenhower’s administration. Through a junta led by Fidel Castro himself for much of his adult life — until a few years before the bearded, military-fatigued dictator died in late 2016. By then, Cuba was being run by his younger brother, Raul Castro, now 95 and seemingly no longer in day-to-day command. Cuba’s current president, Miguel Diaz-Canel, is effectively a Castro regime apparatchik.
Cuba was once a Cold War flashpoint, as a client state of the old Soviet Union. While there was some rapprochement between Cuba and the United States under former President Barack Obama, that’s now a distant political memory.
That’s because the Trump administration in recent months has significantly escalated economic and military pressure on Cuba. The administration is pursuing a policy centered on enforcing a de facto fuel blockade and demanding “fundamental change” on the island.
Many congressional Democrats contend this maximum-pressure campaign has exacerbated an intense humanitarian and energy crisis in Cuba. One that’s led to widespread electrical grid collapses, water shortages, and rolling blackouts, per Rep. Pramila Jayapal (D-WA), a former chairwoman of the House Progressive Caucus.
Jayapal has introduced legislation to prevent unauthorized military action against the island. She led a congressional delegation to Cuba in April 2026. Over the five-day trip, Jayapal, Rep. Jonathan Jackson (D-IL) and a group of like-minded lawmakers met with Diaz-Canel and Foreign Minister Bruno Rodriguez, among others.
At the time, Jayapal described the humanitarian and energy conditions in Cuba as a “crisis beyond imagination.” She also called the U.S. fuel embargo and sanctions an act of “economic bombing” that inflicts collective punishment on civilians.
The episode, not surprisingly, drew scorn and opprobrium from congressional Republicans and Trump administration officials. They labeled the trip shameful, accusing the Democratic lawmakers of legitimizing a communist regime.
Left: President John F. Kennedy (left) walks along a path at Camp David in Maryland with former President Dwight D. Eisenhower as the two met to discuss the Bay of Pigs invasion on April 22, 1961. Right: Fidel Castro (center) with members of the Revolutionary Armed Forces at his base of operations in Jaguey Grande, Cuba, during the Bay of Pigs invasion in April 1961. (Paul Vathis/AP; AP photo)
" data-large-file="https://www.washingtonexaminer.com/wp-content/uploads/2026/10/WB.WhiteHouse3.102126.jpg?w=696" height="658" width="1024" src="https://www.washingtonexaminer.com/wp-content/uploads/2026/10/WB.WhiteHouse3.102126.jpg?w=696" alt="Left: President John F. Kennedy (left) walks along a path at Camp David in Maryland with former President Dwight D. Eisenhower as the two met to discuss the Bay of Pigs invasion on April 22, 1961. Right: Fidel Castro (center) with members of the Revolutionary Armed Forces at his base of operations in Jaguey Grande, Cuba, during the Bay of Pigs invasion in April 1961. (Paul Vathis/AP; AP photo)" class="wp-image-4768469" style="width:349px;height:auto" srcset="https://www.washingtonexaminer.com/wp-content/uploads/2026/10/WB.WhiteHouse3.102126.jpg 1400w, https://www.washingtonexaminer.com/...6/10/WB.WhiteHouse3.102126.jpg?resize=300,193 300w, https://www.washingtonexaminer.com/...6/10/WB.WhiteHouse3.102126.jpg?resize=768,494 768w, https://www.washingtonexaminer.com/.../10/WB.WhiteHouse3.102126.jpg?resize=1024,658 1024w, https://www.washingtonexaminer.com/...26/10/WB.WhiteHouse3.102126.jpg?resize=150,96 150w, https://www.washingtonexaminer.com/...6/10/WB.WhiteHouse3.102126.jpg?resize=696,447 696w, https://www.washingtonexaminer.com/.../10/WB.WhiteHouse3.102126.jpg?resize=1068,687 1068w" sizes="auto, (max-width: 1024px) 100vw, 1024px">
Left: President John F. Kennedy (left) walks along a path at Camp David in Maryland with former President Dwight D. Eisenhower as the two met to discuss the Bay of Pigs invasion on April 22, 1961. Right: Fidel Castro (center) with members of the Revolutionary Armed Forces at his base of operations in Jaguey Grande, Cuba, during the Bay of Pigs invasion in April 1961. (Paul Vathis/AP; AP photo)
Most vocal was Secretary of State Marco Rubio, a longtime fierce opponent of the Cuban regime during his rise in Florida GOP politics. It’s an issue that’s long been central to the political identity of Rubio, a Florida senator for 14 years whose parents immigrated to the U.S. in 1956 during the regime of Fulgencio Batista, two and a half years before Fidel Castro seized power.
Rubio and the State Department strongly opposed the outreach to Cuba by congressional Democrats. The department prohibited the top U.S. diplomat in Havana (Chargé d’Affaires Mike Hammer) from meeting with Jayapal’s delegation.
Yet left-wing validation of the Castro regime is also drawing some Democratic critics. Rep. Josh Gottheimer (D-NJ) took issue with an Aug. 13 Democratic Socialists of America statement on Fidel Castro being born 100 years earlier.
“DSA commemorates the centenary of Fidel Castro and demands an end to the genocidal blockade,” the statement’s headline said.
“Fidel was an organizer, a fighter, and endures as a stalwart symbol of anti-imperialist struggle and self-determination for the Global South,” the statement said, in part. “We choose this historic day to recommit ourselves to acting in solidarity with the Cuban people and to starkly opposing Marco Rubio’s genocidal war against the Cuban people and U.S. imperialism writ large.”
That sentiment didn’t sit well with Gottheimer, elected in 2018 to a House district in northern New Jersey that now covers northwestern New York City suburbs and exurbs.
“DSA is out here celebrating Fidel Castro — a dictator who jailed dissidents, silenced the press, and ran a police state for decades,” Gottheimer said in an Aug. 21 X post. That’s who they are, and they’re proud of it. You don’t get to call yourself a champion of the oppressed while praising the man who crushed the Cuban people for generations.”
Gottheimer is a longtime critic of the Cuban regime. He has previously pushed for the return of U.S. fugitives hiding in Cuba, including cosponsoring congressional resolutions calling for the immediate extradition of convicted felons. Among them was, before her September 2025 death, Joanne Chesimard. She was convicted of the first-degree murder of New Jersey State Trooper Werner Foerster during a shootout on the New Jersey Turnpike in 1973. And William Morales, a Puerto Rican nationalist convicted in February 1979 for possession of explosives, and possession and transportation of explosives and a shotgun.
People carry water during a power outage in Havana, Cuba on Aug. 3. (Ramon Espinosa/AP)
" data-large-file="https://www.washingtonexaminer.com/wp-content/uploads/2026/10/WB.WhiteHouse1.102126.jpg?w=696" height="658" width="1024" src="https://www.washingtonexaminer.com/wp-content/uploads/2026/10/WB.WhiteHouse1.102126.jpg?w=696" alt="People carry water during a power outage in Havana, Cuba on Aug. 3. (Ramon Espinosa/AP)" class="wp-image-4768470" style="width:836px;height:auto" srcset="https://www.washingtonexaminer.com/wp-content/uploads/2026/10/WB.WhiteHouse1.102126.jpg 1400w, https://www.washingtonexaminer.com/...6/10/WB.WhiteHouse1.102126.jpg?resize=300,193 300w, https://www.washingtonexaminer.com/...6/10/WB.WhiteHouse1.102126.jpg?resize=768,494 768w, https://www.washingtonexaminer.com/.../10/WB.WhiteHouse1.102126.jpg?resize=1024,658 1024w, https://www.washingtonexaminer.com/...26/10/WB.WhiteHouse1.102126.jpg?resize=150,96 150w, https://www.washingtonexaminer.com/...6/10/WB.WhiteHouse1.102126.jpg?resize=696,447 696w, https://www.washingtonexaminer.com/.../10/WB.WhiteHouse1.102126.jpg?resize=1068,687 1068w" sizes="auto, (max-width: 1024px) 100vw, 1024px">
People carry water during a power outage in Havana, Cuba on Aug. 3. (Ramon Espinosa/AP)
Following the January U.S. military operation in Venezuela and capture of dictator Nicolas Maduro, Gottheimer released a statement noting that Maduro’s removal dealt a significant blow to regional allies including Cuba, China, and Iran. It fits within a broader, more hawkish worldview by Gottheimer, a House Intelligence Committee member, than that of many House Democrats.
“Gottheimer has long clashed with progressive Democrats, most often over the Israel-Palestine conflict and the broader concern that the far left tolerates antisemitism,” noted the 2026 Almanac of American Politics. “This conflict was supercharged after Hamas attacked Israel on Oct. 7, 2023. Gottheimer strongly supported Israel and defended its response to the attack, while progressives raised humanitarian concerns.”
A history of Democratic splits over Cuba
This kind of intra-Democratic split over Cuba goes back to the communist regime’s earliest days. During the 1960 presidential campaign, on Cuba, Democratic nominee John F. Kennedy ran to the right of his Republican rival, Vice President Richard Nixon. Kennedy pressed a hard-line stance against Fidel Castro’s communist regime.
Kennedy criticized the Eisenhower-Nixon administration for “losing” Cuba to communism. In October 1960, Kennedy even issued a statement favoring direct U.S. assistance and unilateral intervention to support anti-Castro exile forces seeking to overthrow Fidel Castro.
Sure enough, that’s what transpired after Kennedy’s narrow win over Nixon. As president, he approved the April 1961 Bay of Pigs operation, which turned out to be a failed, U.S.-backed and CIA-financed attempt by Cuban exiles to overthrow Fidel Castro’s government.
The botched operation drew condemnation across the ideological spectrum. Conservative criticism focused heavily on what they called Kennedy’s lack of resolve, timid execution, and betrayal of anticommunist allies. It’s an argument present in modern politics. Sen. Tom Cotton (R-AR), in his 2022 book Only the Strong: Reversing the Left’s Plot to Sabotage American Power, condemned Kennedy’s lack of leadership in the Bay of Pigs debacle. Cotton placed it in a long line of foreign policy decisions made by Democratic administrations he says have often resulted in military disasters.
But in Kennedy’s day, biting criticism came just as strongly from the Democratic camp. Sen. J. William Fulbright, the influential Democratic chairman of the Senate Foreign Relations Committee, was the most prominent congressional voice against the operation. Before the invasion, the Arkansas Democrat handed Kennedy a blunt memorandum arguing that a covert assault would violate the United Nations charter and the Organization of American States treaties. He argued that staging a rebellion against a sovereign neighbor would deeply compromise the moral standing of the U.S.
After the operation, a swath of “high-ranking congressional Democrats voiced deep private and public concerns regarding the administration’s strategic judgment and communication failures,” per an article published by the Council on Foreign Relations.
A political rift reflected in music
These kinds of internecine disputes over Cuba have at times moved from the political realm into the musical. Folk singer Joan Baez, known for her left-wing, progressive activism and vocal opposition to the Vietnam War, recorded “Guantanamera” in 1974. The song, with a title translated as “the woman from Guantanamo,” is among the most widely recognized Cuban patriotic songs.
Baez is not known to have outright praised the Castro regime. But her recording of the song on the Spanish-language album Gracias a la Vida offered a less-than-subtle view on the subject. Fidel Castro, by then in power for 15 years, had championed “Guantanamera” as what he called a cultural symbol of the Cuban Revolution’s triumph over Western imperialism.
A more mainstream Cold War liberal approach to Cuba can be heard in the closing stanzas of “Suite: Judy Blue Eyes,” the classic folk rock song written by Stephen Stills and performed by the supergroup Crosby, Stills & Nash. The multipart harmony track, released in September 1969 as it led off their group’s self-titled debut album, had a slow burn in popularity. It only reached 21 on the Billboard Hot 100, but its fandom has since grown exponentially. To the point that it’s frequently included in lists such as Rolling Stone’s “500 Greatest Songs of All Time.”
The final, most famous section of the song includes Spanish lyrics, joyful, upbeat vocal harmony, and Stills’s intricate guitar work:
“Qué linda, me la traie a Cuba
La reina de la Mar Caribe
Cielo, sol…
Y qué triste que no puedo vaya / bailar”
“How nice it will be to take you to Cuba
The queen of the Caribbean Sea
I only want to visit you there
And how sad that I can’t, damn!”
On its face, the song might appear to be a paean to revolutionary Cuba. Yet, it’s anything but. It’s about his disintegrating relationship with folk singer Judy Collins.
FLORIDA PROFESSOR VISITED CUBA SEVERAL TIMES BEFORE DESANTIS APPOINTEE’S SECURITY WARNINGS
It’s also a wistful, nostalgic reflection on the island’s natural beauty and the singer’s sadness over being unable to visit it. Stills, born in 1945, grew up partly in Florida. He spent part of his youth traveling and vacationing in Cuba with his family right up until the 1959 Cuban Revolution. His lyrics reflect a longing for the prerevolutionary, open paradise he remembered as a child, rather than an endorsement of Fidel Castro’s regime.
That gels with songwriter Stills’s mainstream liberal political outlook. He has attended many Democratic national conventions and performed remotely in 2020 amid the COVID-19 pandemic. And at the 2000 party confab in Los Angeles, he was a member of the Credentials Committee representing the state of Florida.
David Mark (@DavidMarkDC) is the managing editor of the Washington Examiner magazine.
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[ H/T Washington Examiner ]
