Cuba Libre
Eisenhower. Kennedy. Johnson. Nixon. Ford. Carter. Reagan. Bush. Clinton. Bush. Obama. Trump. Biden. And now Trump again. This is how many administrations have gone by in the United States while a Castro has been in charge of Cuba. Many think that the Castro regime ended with the death of Fidel, but that’s hardly the case. His more ideologically minded and ruthless brother Raul carried on during Fidel’s illness and thereafter, and his son is now purportedly still very much in charge of the communist party’s affairs, which is to say the island nation as a whole.
My wife and I traveled to Cuba during the brief reprieve under Obama when Americans could travel on a cultural visa. It was a short-lived period toward the end of his term that was repealed immediately during Trump’s first term. As a Canadian-born American I was excited to finally travel to a place that most of my Canadian relatives had been to several times. For Canadians, travel to Cuba was like Americans going to the Dominican. No big deal. But you would think we went to the fucking moon by how our American friends responded.
Canadian tourism dollars have poured into the Cuban economy for decades, making Canada one of the island’s most reliable economic lifelines. So it’s no surprise that as the current crisis deepens, many Canadians are experiencing a genuine crisis of conscience. They’ve watched Cuba deteriorate in real time over successive visits, seen the shelves get emptier and the blackouts get longer, all while knowing their own government refuses to say a word about it.
Publications like Canadian Dimension and advocacy groups like the Canadian Network on Cuba have long sounded the alarm. They’ve condemned Ottawa’s silence in the face of Washington’s escalating economic warfare, calling out what they see as a cowardly abdication of principle. Isaac Saney, a member of the CNC’s executive committee, has sounded the alarm that this is perhaps the most dangerous moment the Cuban Revolution has ever confronted. And yet the Carney administration has offered nothing. Not a statement. Not a rebuke. Not even a throat clearing at the United Nations.
Like other defenders of the western liberal order, Carney stood in Davos just weeks ago extolling Canadian values like human rights, sovereignty, and solidarity. All in defiance of Trumpian authoritarianism. Meanwhile, the United States is openly strangling Cuba’s energy supply and causing a legitimate and severe humanitarian crisis on the island.
Two former Canadian ambassadors to Cuba have attributed this silence to Ottawa’s desperation to secure a renewed trade deal with the United States, which is to say Canada’s moral compass has been placed on the negotiating table alongside lumber tariffs and dairy quotas.
None of this is to suggest the longstanding Castro regime deserves a pass. The brothers Castro presided over a repressive, authoritarian state for more than half a century. Political prisoners rotted in Cuban jails. Dissent was crushed. The press was muzzled. Raul was arguably more ideologically rigid than Fidel, a true believer in the Marxist-Leninist project who ran the security apparatus with an iron fist. These aren’t inconvenient footnotes. They’re central to the story.
But so is this: when Fidel Castro came to power in January 1959, his first instinct wasn’t to call Moscow. It was to come to Washington. Just months after the revolution, Castro accepted an invitation from the American Society of Newspaper Editors and traveled to the United States for an eleven-day visit. He wanted to talk. He wanted a relationship. And Eisenhower literally went golfing to avoid him. The President of the United States couldn’t be bothered to meet the new leader of a nation 90 miles off the coast of Florida. Castro was handed off to Vice President Nixon, and the two disagreed on virtually everything. Nixon walked away convinced Castro was a dangerous leftist. The die was cast.
What followed was predictable. The U.S. demanded immediate compensation for nationalized American properties. Castro offered bonds payable over 20 years. Washington said no. Castro invited Soviet officials to Havana and asked American-owned refineries to process Russian crude. The State Department told them to refuse. Castro then had his justification to seize the refineries, and the whole thing spiraled from there—Bay of Pigs, the missile crisis, the embargo, 60+ years of mutual hostility.
Castro wasn’t born a Soviet client. He was a revolutionary and, yes, a dictator, but above all a dealmaker and a pragmatist. He wanted American partnership first. When it was denied, he took the only other deal on the table. You’d think a country that has celebrated its own gangster capitalists, its robber barons, and its ruthless negotiators would have recognized a kindred spirit. Instead, we turned him into exactly the monster we feared, and then spent six decades punishing the Cuban people for it.
Which brings us to right now, February 2026, and a situation that can only be described as a slow-motion humanitarian catastrophe. Since the Trump administration seized Venezuelan President Maduro in January, Cuba’s primary oil lifeline has been severed. Washington then pressured Mexico’s state oil company into compliance, and imposed tariffs on any country that dares sell oil to the island. In a single month, 77% of Cuba’s oil imports vanished.
The island now has roughly 15–20 days of reserves as of this writing. Schools have shortened their days. Universities have cut in-person attendance. Tourism facilities have shut down. Families are cooking with wood and coal. Bus stops sit empty. Hospitals are rationing power. The UN Secretary-General has said he is “extremely concerned” that the situation will worsen or collapse entirely if Cuba’s oil needs go unmet.
Regardless of where you stand on Cuba’s government, reporting from Drop Site News, corroborated by five Cuban and U.S. officials, indicates that Secretary of State Marco Rubio is actively sabotaging diplomatic talks between Washington and Havana. According to these sources, Rubio has been telling Trump that negotiations are underway when they are not—the idea being that in a few weeks or months, Rubio can claim the talks failed because of Cuban intransigence, leaving regime change as the only option. Trump, who reportedly holds a registered trademark for a property in Havana and has expressed interest in a deal, doesn’t appear to be ideologically committed to crushing Cuba. But Rubio is. This has been his life’s project. Trump even shared a Truth Social post suggesting Rubio should be Cuba’s next president, to which Rubio’s camp responded with enthusiasm.
There would be a deep and bitter irony if this is how it ends for Cuba nearly 70 years after Fidel Castro liberated Cuba from American capitalists and gangsters who controlled gaming and tourism. Seventy years and 13 American administrations. The Bay of Pigs. Cuban Missile Crisis. Collapse of the Soviet Union and the “Special Period.” All potentially undone by America’s most vicious gangster capitalist and casino mob boss.
