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The Latest Breaking News from Cuba

From Caracas to Havana: Why Trump's Venezuela playbook may fail in communist Cuba

US president Donald Trump's presidency has shifted to muscular interventionism, beginning with the swift overthrow of Venezuela's Maduro. Now, the focus turns to Cuba, but unlike Venezuela, the island presents a more cohesive political structure, a disciplined military, and a population prepared for conflict, making the 'Venezuela model' unlikely to…

The Times of India

Why was HasanAbi subpoenaed by the US Treasury? Cuba trip controversy explained

Hasan Piker is facing federal scrutiny after the U.S. Treasury’s Office of Foreign Assets Control reportedly issued subpoenas connected to his March 2026 Cuba trip. Authorities are investigating whether participants violated U.S. sanctions laws through financial or travel-related activities involving Cuban government-linked entities. HasanAbi denied wrongdoing, saying, “we stayed at…

The Times of India

Hasan Piker reportedly under scrutiny over Cuba sanctions investigation

The Times of India

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Livestreamer Activist Hasan Piker Hit With Federal Subpoena Over Cuba Trip Tied With Alleged Communists

US federal officials are investigating livestreamer Hasan Piker and others for potential sanctions violations during a March trip to Cuba, focusing on financial and organisational activities.

International Business Times UK

Trump's next phony war: Cuba, beware

What Iran war? In desperate search of a legacy, Trump goes after Cuba’s failing regime. It's sad on both sides

Salon

Is United States on verge of a Maduro-like military intervention in Cuba?

The US under Trump is intensifying pressure on Cuba, drawing comparisons to its Venezuela policy. However, experts believe Cuba's complex political structure and disciplined security apparatus make it a far riskier and potentially costlier challenge for Washington than Venezuela.

The Times of India

Despite Trump's pressure, Cuba may not turn out like Venezuela

The U.S. is increasing pressure on Cuba, but unlike Venezuela, the island nation lacks a clear opposition leader or succession plan. Cuba's cohesive and ideologically entrenched government, coupled with U.S. legal constraints and its state-run economy, present significant challenges to regime change efforts.

The Economic Times

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Trump’s ‘Don-Roe Doctrine’ Just Backfired as Russia Steps in to Save Cuba From His ‘Sanctions Noose’

Trump’s maximum pressure campaign is pushing Cuba straight into Russia’s arms.

The Mary Sue

ICE Arrests Sister Of Cuba Military Conglomerate Chief In Miami As U.S. Ramps Up Pressure On Havana

U.S. Immigration & Customs Enforcement (ICE) has detained the sister of the woman who heads Grupo de Administración Empresarial S.A. (GAESA), Cuba's powerful military-run conglomerate, in Miami, as Washington continues to ramp up pressure against Havana.

International Business Times

‘This is his legacy’: Marco Rubio nears goal of toppling Cuba’s government

US secretary of state’s campaign of ‘maximum pressure’ is culmination of a personal pursuit spanning decades

The Guardian - UK

Is the US preparing for military action against Cuba? Expert Q&A

A US court filed criminal charges against Cuba’s 94-year-old former leader, Raúl Castro, on May 20. Castro has been charged with conspiracy to kill US nationals, four counts of murder and two counts of destruction of aircraft. The charges relate to a 1996 incident in which four men were killed…

The Conversation

Who Abuses Food Delivery?

Plus: Cuba court case, Iran war vote, Knicks watch, and more...

Reason

U.S. Officials Reportedly Developing Military Options For Cuba To Present To Trump

The U.S. intelligence community is reportedly analyzing how the Cuban regime would respond to military action in the country as the Trump administration ramps up pressure on the regime.

International Business Times

Cuba needs a long-term solution to its energy crisis

Cuba has run out of oil, the country’s energy minister announced on May 14, 2026.

The Conversation

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The Independent UK

Trump turns screws on Cuba as Rubio warns military action is on the table

IN FULL

The Economic Times

Rare public appearances, low profile mark Raul Castro's life since stepping down as Cuba's president

Former Cuban President Raul Castro is now facing serious charges from US prosecutors. These accusations relate to a 1996 incident where civilian planes were shot down. This development has intensified existing tensions between the United States and Cuba. Cuba's government has strongly condemned the indictment. Protests are planned in Havana.…

The Independent UK

Trump threatens new Cuba crackdown as Rubio warns Havana: ‘We’re very serious’

Speaking from the Oval Office, Trump hinted he could be the president who finally takes direct action against Havana after decades of failed threats from Washington

Roll Call

Democrats renew effort to prevent US military action against Cuba

A trio of Senate Democrats is trying again to rein in President Donald Trump’s ability to order military action against Cuba. Sens. Tim Kaine, D-Va., Adam B. Schiff, D-Calif., and Ruben Gallego, D-Ariz., have introduced a war powers resolution that would direct Trump to “remove the United States Armed Forces…

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Euronews

Rubio doubtful diplomacy would work with Cuban government as Trump raises threat of military action

Rubio says the White House is very focused on toppling the socialist government of Cuba to address what he says are national security risks. He also stressed that Havana will not be able to outwait the Trump administration, urging them to strike a deal before it is too late.

AAP

US arrests sister of Cuban military conglomerate chief

The Trump administration has arrested the sister of a top Cuban official who heads a military conglomerate.

France 24

Rubio questions Cuba diplomatic path as Trump raises prospect of military action

US President Donald Trump and Secretary of State Marco Rubio on Thursday renewed suggestions of possible military action against Cuba, a threat amplified by Washington's criminal charges a day earlier against former Cuban leader Raúl Castro. Trump said US presidents had long considered intervention and suggested he could be the…

Reason

Why Does Trump Keep Bringing Up Decades-Old Foreign Grievances?

Instead of making the case for war in Venezuela, Iran, and Cuba, the White House has been digging up conflicts from long ago.

International Business Times

Supreme Court Sides With U.S. Company In Cuba Property Seizure Case

The Supreme Court on Thursday sided with Havana Docks Corp. in a long-running fight over property seized by Fidel Castro's regime after the Cuban Revolution.

The Independent UK

Indictment of former Cuban president includes 5 fighter jet pilots involved in 1996 plane downings

Federal authorities in the United States have charged former Cuban President Raúl Castro and five fighter pilots in the 1996 downing of civilian planes operated by Miami-based exiles

Euronews

Rubio says US focused on changing politics in Cuba as Havana accepts €86m in aid

Rubio, a Cuban-American and vociferous opponent of Havana's government, described the island 145 kilometres from the US shore as a "failed state" as it suffers a major economic crisis.

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