History Will Tell How Canada’s Spies Helped Trump in Cuba

Canada has long assisted the US bid to suffocate Cuba. And the roots of intelligence sharing undercut the idea of Ottawa standing up to US bullying.

On Saturday the Globe and Mail confirmed that Canada has long spied on Cuba for the US. In “Canadians passed intelligence to U.S. at time of alleged attacks in Cuba: source”, Robert Fife reports, “A Canadian diplomat was sharing intelligence with American spies in Havana and Canadians were using satellite equipment brought into Cuba by the United States when officials from both countries began experiencing debilitating symptoms caused by alleged sonic attacks linked to Russia.”

The long story about the 2017 “Havana syndrome” describes how a Canadian diplomat gathered human intelligence on the island, which was often passed on directly to a CIA agent at the US embassy. Another source told Fife that “Canadians were using satellite equipment brought in surreptitiously by the United States.” The information gathered was sent to the intelligence division at Global Affairs, CSIS and to Five Eyes partners (US, Britain, Australia and New Zealand). Fife added, “the two sources said the Canadian embassy’s intelligence-gathering was valued by the U.S. because of Canada’s longstanding friendship with Cuba. Unlike the Americans, Canadian diplomats had better access to Cuban officials and were allowed to travel outside of Havana.”

As has been documented by multiple sources, including the 2015 International Journal article “Our men in Havana: Canadian foreign intelligence operations in Castro’s Cuba”, Canada has spied for the US since the Cuban revolution. In fact, Washington’s request for Canadian spying assistance is part of the reason Ottawa didn’t sever diplomatic relations with Havana after the 1959 revolution. In the 2007 book Three Nights in Havana: Pierre Trudeau, Fidel Castro, and the Cold War World Robert Wright explains: “Recently declassified State Department documents have revealed that, far from encouraging Canada to support the embargo, the United States secretly urged [Prime Minister John] Diefenbaker to maintain normal relations because it was thought that Canada would be well positioned to gather intelligence on the island.”

Ottawa did not let Washington down. The Communications Security Establishment (CSE), Canada’s NSA, listened to Cuban leaders’ secret conversations from an interception post in the Canadian embassy in Havana and Canadian diplomats were among the first to alert the US to incoming Soviet arms and troops before the October 1962 Cuban Missile Crisis. A senior Canadian official, close to Washington, in Inside Canadian intelligence: exposing the new realities of espionage and international terrorism “admitted that the U.S. made ‘far greater use’ of our intelligence during the Cuban Missile Crisis than has been revealed.” Pentagon and State Department sources cite the UK and Canada as the only countries that “supply any real military information on Cuba” with Canada providing “the best” military intelligence.

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Cuba In Crosshairs: US Army Reportedly Checks Troop Availability As Trump Says Communist Regime “Will Fail”

President Trump told the United Nations General Assembly on Tuesday that the failed communist island nation of Cuba would see freedom, as the U.S. has not been shy about its intentions to kick the communist regime out of Havana. The U.S. has employed gunboat diplomacy through an oil blockade this year, as the failed state has seen its economy collapse even further.

“My administration is also seeking a fundamental change in the situation in Cuba, where the communist regime is under great pressure, the biggest pressure they’ve ever been under. It’s an absolutely failed state; it’s failing like never before, and it will fall,” Trump said in his speech at UNGA.

With Trump’s UNGA comments in mind, CBS News reports that it has reviewed an internal Army memo assessing the availability of military police, medical teams, and logistics units for possible use under Southern Command within 90 to 120 days.

The memo does not mention Cuba, identify troop numbers, or specify an operation. It also contains no indication that units have received deployment orders so far.

Here’s more color from the report:

The document reviewed by CBS News says Army Reserve headquarters is seeking feedback from subordinate commands on the possible availability of six types of formations that would fall under the authority of U.S. Southern Command. The units would “possibly [be] needed in 90-120 days,” according to the message, which directs commands to provide feedback to Army Reserve headquarters by Sept. 25. 

Among the units is a combat sustainment support battalion that specializes in coordinating logistics such as transportation, maintenance, fuel and supply needs, along with an engineer battalion. The document also seeks an expeditionary sustainment command that would oversee logistics across a theater of operations. 

The document generated last week also calls for a medical brigade to command and coordinate medical units, as well as a forward resuscitative and surgical detachment to provide emergency surgery and trauma care closer to U.S. forces. Finally, the document seeks a military police brigade — these units typically oversee military police forces responsible for security, detention and other law enforcement missions. 

In July, CBS reported that military planners had examined an air assault involving thousands of soldiers from the 101st Airborne Division. Another report by Politico in August suggested that the U.S. intelligence community had “sent spies and assets” to Cuba. Specifically, the outlet reported that the CIA had increased its presence on the island, which sits about 90 miles south of Florida.

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U.S. military lays groundwork for potential action around Cuba

The U.S. Army Reserve is examining whether it can provide the military’s Southern Command with police forces, medical personnel and other support units within the next four months, according to an internal Army message reviewed by CBS News.

Though the message makes no reference to Cuba, the request is for continued military planning aimed at Cuba, according to multiple U.S. officials who spoke to CBS News under condition of anonymity because they were not authorized to speak publicly.

There is no indication in the document that any units have received deployment orders. But the planning comes as the Trump administration puts intense economic pressure on Cuba and urges the island nation to make political reforms.

The message does not identify how many troops would be needed in the Southern Command’s region, which covers Central and South America, including the Caribbean. It also does not specify where the forces could be sent or what operation they would support. 

The document reviewed by CBS News says Army Reserve headquarters is seeking feedback from subordinate commands on the possible availability of six types of formations that would fall under the authority of U.S. Southern Command. The units would “possibly [be] needed in 90-120 days,” according to the message, which directs commands to provide feedback to Army Reserve headquarters by Sept. 25. 

Among the units is a combat sustainment support battalion that specializes in coordinating logistics such as transportation, maintenance, fuel and supply needs, along with an engineer battalion. The document also seeks an expeditionary sustainment command that would oversee logistics across a theater of operations. 

The document generated last week also calls for a medical brigade to command and coordinate medical units, as well as a forward resuscitative and surgical detachment to provide emergency surgery and trauma care closer to U.S. forces. Finally, the document seeks a military police brigade — these units typically oversee military police forces responsible for security, detention and other law enforcement missions. 

Contacted by CBS News, the Army Reserve did not respond before publication. 

A spokesperson for U.S. Southern Command said: “Due to operational security concerns, we do not disclose details or comment on U.S. operational movements or potential deployment timelines associated with current or future operations, contingencies, or planning. However, U.S. Southern Command continuously coordinates with the Joint Force to assess a range of potential requirements across its [area of responsibility] in support of assigned missions.” 

Earlier this year, American forces conducted reconnaissance operations on the seafloor and maritime approaches surrounding the Cuban island, multiple U.S. military personnel told CBS News. Separately, U.S. airpower components were placed on heightened readiness and directed to pre-stage personnel for potential deployment. Those plans, however, did not come to fruition. CBS News is withholding certain details from publication that could potentially put U.S. service members at risk.

CBS News reported in May that U.S. intelligence officials were assessing how Cuba would respond to possible U.S. military action, as the Trump administration accused Havana of strengthening ties with Russia, China and Iran. The intelligence community’s 2026 annual threat assessment largely portrays Cuba as an enabling environment for larger geopolitical competitors, rather than as an independent strategic threat.

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DSA Democrats Praise This ‘Socialist Model’ – Communist Cuba’s Power Grid Collapses

The power grid in Cuba has once more failed, leaving residents of the Caribbean island in darkness.

Reuters reported on Friday that the electrical grid sustained a “total collapse” as millions were left entirely without power.

The outlet noted that the collapse of the power grid was driven by high-voltage transmission lines failing in central Cuba around 2 p.m.

Felix Estrada, an ⁠official with Cuba’s National Electrical Union, said in a statement that “protocols are now in place to begin ​the gradual restoration of the system.”

Some neighborhoods in Havana — especially those near hospitals — had their power restored by Friday evening.

But the rest of Cuba’s capital and largest city remained dark even as clouds and rain gathered.

Reuters reported that there have been at least six partial or total blackouts so far this year in Cuba.

There were three collapses in July alone.

The outlet added that many in Havana are accustomed to the grid failing, and are used to enduring many hours or even days without power.

“Yesterday I’d gone without ‌power ⁠for 24 hours. They turned the lights on for an hour, and then the grid collapsed,” Frank Lorenzo, a 23-year-old Havana resident, told Reuters.

Reuters noted that the power grid has been placed under additional strain by the U.S. oil blockade that started in January.

The Council on Foreign Relations said in a 2023 analysis that the nation’s communist regime was at its weakest point in decades — even before the most recent woes.

“Cuba’s centrally planned economy has been mired by stagnation for decades. But over the past five years, the pillars propping up the island’s already feeble economy collapsed one by one, sending it into a tailspin,” the think tank noted.

Among other factors, oil production from Venezuela declined, while Brazil and Colombia nixed arrangements under which Cuba sent medical professionals to work abroad and took most of their pay.

Cuban tourism also plummeted with COVID lockdowns.

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Cuba Hit With National Power Grid Collapse As Oil Sources Dry Up

Cuba’s power grid collapsed once again this week, this time at a national level, leaving millions of people across the island without electricity.  This is the sixth time since the US cut off fuel sources to the island since January that the national grid has collapsed and it’s the most utility shutdown events in the country’s recent history.  

Even when Cuba’s grid is in operation, only 30% of the population at most receives electricity at any given time.  Many regions stay dark 20 to 30 hours at a stretch. Some provinces have reported 60–90 hours without power. Havana has gone from 4 hours a day early in the year to 18 hours after the fuel cutoff. 

“Protocols are now in place to begin ​the gradual restoration of the system,” said Felix Estrada, an ⁠official with Cuba’s National Electrical Union (UNE). Power had returned to a handful of ​scattered neighborhoods in Havana by late evening, primarily around hospitals, but much of ​the city remained completely dark.

Many exhausted residents ​of the capital Havana were already without power when the national blackout hit.

“Yesterday I’d gone without ‌power ⁠for 24 hours. They turned the lights on for an hour, and then the grid collapsed,” said Frank Lorenzo, a 23-year-old Havana resident.

Around 61% of Cuba’s oil was sourced from Venezuela until the US capture of illegitimate president Nicolas Maduro.  Shipments from Mexico have were also scaled back and then cut off.  Russia has sent only one tanker so far this year. 

Reports of a “shadow fleet” of tankers carrying Iranian oil to Cuba have circulated since at least 2020.  Investigations of the seized tanker “Skipper” in 2025 found it had previously carried Iranian oil to Syria and China, then later moved Venezuelan oil on a route tied to Cuba. It confirmed the existence of overlapping Iran–Venezuela–Cuba shipping networks. 

The US blockade of the Strait of Hormuz has proven incredibly effective in shutting down Iranian oil exports, leaving Iran’s clandestine trade partners high and dry.  

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DSA Member Embarrassed AGAIN After Confronted with Realities of Communist Cuba

The Gateway Pundit reported that the National Co-Chair of the Democratic Socialists of America, Ashik Siddique, became a bumbling mess when confronted by Latino journalist Jorge Ramos, when he was asked a simple question about whether or not Cuba is a dictatorship.

He immediately tried to make the issue about Trump and the blockade on Cuba, because he could not answer the question honestly.

CNN’s Boris Sanchez confronted Siddique over the organization’s unfounded praise of Cuba, and shared the story of his anti-Batista grandfather being imprisoned by Castro to drive home the realities of the regime.

Once again, Siddique was so shaken that he couldn’t form a response.

Sanchez told Siddique, “I get your criticism of foreign policy. As I said, it’s not an uncommon one, but lauding Fidel Castro is a different story.”

“You talk about what things were like before the revolution in Cuba. I’ll give you a personal example. My grandfather was a revolutionary in Cuba during that time. He was affected by a previous dictator, Fulgencio Batista, having his friends disappeared in the street for speaking their minds.”

“My grandfather found that revolution, hoping to bring democracy to Cuba, and then what happened?”

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DSA Members Can’t Bring Themselves to Admit Cuba is a Dictatorship – Immediately Try to BUT TRUMP!

During a recent conversation with Latino journalist Jorge Ramos, high ranking members of the DSA turned into a stuttering mess when they were asked a simple question about whether or not Cuba is a dictatorship. HINT – It is.

They immediately try to make the issue about Trump and the blockade on Cuba, because they cannot answer this question honestly.

Ramos keeps trying to give them an opportunity to answer the question, pointing out that Cuba has not had real elections in decades, engages in all forms of censorship and has political prisoners, but they just won’t embrace the truth.

From Stu Smith:

DSA Co-Chairs Squirm When Pressed on Cuba, Venezuela, and Nicaragua

This is a longer clip, but it captures the best parts of a broader discussion DSA national co-chairs Ashik Siddique and Megan Romer had with The Moment hosts Jorge Ramos and Paola Ramos.

Jorge repeatedly presses them on whether Cuba, Venezuela, and Nicaragua are dictatorships. They repeatedly avoid giving him a direct answer.

Romer eventually responds that “Cubans have access to their democracy in a way that we do not,” pointing to Cuba’s 2022 Family Code referendum as evidence. That referendum was only four years ago, making it an especially curious answer to Jorge Ramos repeatedly pressing her on decades without multiparty elections.

Ashik Siddique fares little better. Asked whether Cuba is a dictatorship, he pivots to the U.S. embargo and the state of American politics, responding that “it’s hard for us to judge other countries being dictatorships when we have Donald Trump as president.”…

When it comes to international politics, DSA is often at its most revealing. Siddique and Romer are not even among the organization’s most die-hard internationalists. This is really just the tip of the iceberg when it comes to how radical DSA’s international politics can get.

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Veterans For Peace Condemns Marco Rubio’s Threats Against Cuba and Against US Peace and Solidarity Activists

Veterans For Peace has issued a strong condemnation of Marco Rubio’s McCarthyite report, Cuba, the Capital of 21st Century Communism, which was released by the State Department on July 20. The 100-page document charges Cuba with interfering in the internal affairs of the United States, while accusing U.S. peace and solidarity activists of being foreign agents of Cuba.

“Talk about turning things on their head,” responded Veterans For Peace. “It is the U.S. that has waged an economic war against Cuba for 64 years with a blockade that prevents it from normal trade relations with the U.S. and other countries, stunts its economic development, and denies it access to medicines and other essentials.

“It is the U.S. CIA that organized a failed Bay of Pigs invasion of Cuba in 1961, setting the stage for the 1962 Cuban missile crisis that almost led to a nuclear war. It is the U.S. that is currently enforcing a deadly oil embargo on Cuba, and it is the U.S. president and secretary of state who are openly threatening a U.S. military invasion of Cuba. What has Cuba ever done to the U.S.? Cuba is being punished for declaring its independence from U.S. imperialism and for attempting to develop a socialist economic model that is not based on exploitation and profiteering.

“We reject the Trump administration’s sudden return to “anti-communism” as a means of undermining the credibility of its political opponents — whether from the Democratic Party or actual left-wing organizations. If this is an attempt to intimidate those who are organizing for a just and peaceful world, it will not work. We will not be intimidated. If Trump’s and Rubio’s sudden obsession with “communists” and “political terrorists” is telegraphing their intention for a clampdown on dissent in the U.S., we take this very seriously.

“As veterans and active duty military, we swore an oath to “defend the U.S. Constitution from all enemies, foreign and domestic.”  We take this oath very seriously — more so than ever as the domestic enemies of our democracy ominously rear their ugly heads.  We will resist.

“Veterans For Peace will not be intimidated. We stand in solidarity with Cuba and with all those who struggle for human rights and democracy in the U.S. We will support active-duty military members who refuse to participate in an illegal invasion of Cuba. We also encourage service members to refuse illegal orders to support racist ICE raids or to suppress our First Amendment rights to freedom of speech and assembly in the U.S.” 

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A Secret Cuban CIA Task Force?

Before I get into this, I just want to say that all of this is coming from anonymous sources. Neither the White House nor the CIA has commented on it, and I can’t independently confirm it. More often than not, anonymously sourced MSM articles on Venezuela and Cuba tend to be false or only have bits of truth sprinkled in, but I felt this topic was worth a mention as we watch the Donald Trump administration work toward a free Cuba. So, take them with a grain of salt. They may or may not be true, but here’s what Politico and the New York Times are reporting this week. 

First up, on Tuesday, Politico reported that the United States has increased its intelligence presence in Cuba in recent months. It claims that it could lead to actions “ranging from a U.S. military operation in Cuba to stepped up efforts to turn Cuban officials or ordinary citizens against the regime.” 

This came from two individuals “familiar with the situation.” Here’s more: 

One of the individuals said the U.S. has recently sent spies and assets to Cuba. The person declined to specify the scope of the increased intelligence collection effort or which U.S. agencies are involved because they didn’t want to risk giving details that could compromise operations. The U.S. has 18 offices and agencies that make up the intelligence community.

The second person described the move as increasing the CIA’s ‘presence’ recently but declined to specify timeframes or who was involved.

Both people were granted anonymity because the topic involves sensitive intelligence.

One person described the move “as a key tactical step that could pave the way for a U.S. military incursion,” but said that nothing is set in stone. The other said that Trump still prefers to work this situation through diplomatically.   

On Wednesday afternoon, the New York Times saw the Politico “increase intelligence presence story” and raised it to a “secret Cuba task force.”    

“The CIA has secretly established a Cuba task force, setting in motion plans for a more concerted campaign to pressure the Cuban government to make the economic, political and leadership changes demanded by President Trump,” the Times reports, according to “people briefed on the action.”

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Report: U.S. expands CIA presence and intelligence operations in Cuba

The United States has increased its intelligence assets in Cuba in recent months, including deploying additional spies and expanding the Central Intelligence Agency’s presence on the island, according to a report published by POLITICO.

Citing “two people familiar” with the Trump administration’s plans, the move is allegedly part of a broader effort to pressure Cuba’s communist government to reform or collapse and could support options ranging from stepped-up efforts to recruit Cuban officials or citizens to a potential U.S. military operation.

The intelligence expansion follows a rare high-level visit to Havana in mid-May 2026 by CIA Director John Ratcliffe.

During the trip, Ratcliffe reportedly met with Raúl Guillermo Rodríguez Castro, the grandson of former Cuban leader Raúl Castro, Interior Minister Lázaro Álvarez Casas and the head of Cuban intelligence services.

He personally delivered President Donald Trump’s message that the United States is prepared to engage seriously on economic and security issues only if Cuba makes fundamental changes. The discussions also covered intelligence cooperation, economic stability and security concerns, with emphasis that Cuba can no longer serve as a safe haven for U.S. adversaries such as Russia and China in the Western Hemisphere.

Senior officials accompanied Ratcliffe, with a subsequent report revealing that the delegation included a paramilitary operator involved in the earlier U.S. capture of former Venezuelan dictator Nicolás Maduro.

In tandem with the intelligence expansion, Washington significantly intensified aerial surveillance around Cuba starting early this year — flooding the surrounding airspace with P-8 Poseidon maritime patrols, RC-135 Rivet Joint reconnaissance planes and high-altitude MQ-4 drones.

Cuban officials have since criticized the heightened U.S. intelligence and related pressure as “unlawful attempts to destabilize the island.” Nonetheless, Trump administration officials maintain that a stronger intelligence posture is necessary to protect American national security, track foreign adversaries operating in Cuba and maintain leverage as economic conditions deteriorate and diplomatic talks remain stalled.

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