Trump Tells Cuba to Make a Deal: Ultimatum Explained

With 75% of Cuba’s crude oil supplies cut off following Venezuela’s leadership transition, the Trump administration has ratcheted up pressure on Havana in a way that hasn’t been seen in decades. So what exactly is Washington demanding, and does Cuba have any realistic options left? This article walks through the ultimatum, the leverage, and what happens next.

Statement Date: January 11, 2026 · Key Trigger: Venezuelan oil cutoff · US Leverage: 75% oil supply cut · Talks: April 10, 2026 State Department delegation in Havana

The key facts table below summarizes the main points of the crisis.

Does the US still pay Cuba for Guantanamo Bay?

The U.S. has paid Cuba a nominal rent for the Guantanamo Bay Naval Base since 1903, and those payments have continued even as bilateral relations deteriorated. Cuba has historically refused to cash those checks—but the arrangement itself remains one of the few formal ties that survived decades of Cold War hostility and the subsequent embargo.

Lease history

The lease agreement dates back to a 1903 treaty between the United States and Cuba, which granted the U.S. control over the 45-square-mile base in exchange for an annual payment. The original rent was set at $2,000 per year in gold; the payment has since been adjusted but remains comparatively modest given the strategic value of the location.

Current payment status

Cuba has repeatedly refused to accept the rent payments, a symbolic gesture that underscores its long-standing objection to the American presence on the base. The U.S., for its part, continues to deposit the payments—currently around $4,000 per year—into an account that Cuba has refused to touch.

Did the US offer to buy Cuba?

The idea of the United States purchasing Cuba has surfaced periodically over the centuries, most notably during the post-Civil War period when American politicians briefly considered acquiring the island as a potential expansion opportunity. However, the Spanish-American War of 1898 and subsequent treaty arrangements shifted the focus toward Puerto Rico and the Philippines rather than Cuba.

Past purchase attempts

During the James Monroe and John Quincy Adams administrations, American officials discussed acquiring Cuba as a potential safeguard against British expansion in the Caribbean. These discussions never progressed to formal offers, and the diplomatic landscape changed significantly after the Spanish-American War transformed the region’s dynamics.

Cuba-US relations overview

Relations between Washington and Havana have been marked by revolution, embargo, and occasional diplomatic openings since 1959. The Trump administration’s current approach—combining aggressive economic pressure with signals of openness to negotiation—represents a notable shift from the pattern of either engagement or punitive isolation that characterized previous administrations.

Is Trump negotiating with Cuba?

Trump administration officials have held direct talks with Cuban counterparts in April 2026, a development that marks a significant departure from the confrontational posture that preceded it. A senior State Department delegation landed in Havana on April 10, 2026, for what both sides described as substantive discussions.

Recent statements

Trump has made a series of public statements urging Cuba to strike a deal. At the Shield of the Americas summit, he declared that “Cuba’s in its last moments of life as it was. It’ll have a great new life…That’ll be an easy one.” The president also posted on social media that Venezuela had been supplying oil and money to Cuba, adding that “there’ll be no more oil or money going to Cuba. Zero.”

Negotiation signals

The April 10 talks in Havana addressed prisoner releases, economic reforms, internet connectivity, property claims, and political freedoms. U.S. officials met with Raúl Castro’s grandson, Raúl Guillermo Rodríguez Castro—known as “The Crab”—during the discussions. Cuba’s foreign ministry confirmed the talks, calling them “professional and respectful” while disputing the characterization of deadlines.

Who is Cuba’s main ally?

Venezuela has historically been Cuba’s most critical ally, providing the bulk of the island’s oil imports and serving as a diplomatic shield against American pressure. Following the ouster of Nicolás Maduro’s leadership approximately six weeks before February 2026 reporting, that relationship has been fundamentally disrupted—and Cuba’s energy security along with it.

Key partners

Russia has emerged as a vocal supporter of Cuba during the current crisis, publicly accusing the United States of attempting to “suffocate” the island and announcing plans to send additional oil supplies. However, Russia suspended civilian flights to Cuba after evacuating its tourists, a move that highlighted the limits of Moscow’s commitment.

Venezuela role

About 75% of Cuba’s oil imports typically came from Venezuela and Mexico. With Venezuela’s leadership transition and Mexico’s decision to cease petroleum exports following American pressure, the island has lost access to the overwhelming majority of its external energy supply. Cuba produces only minimal quantities of oil domestically—not nearly enough to sustain its economy or electric grid.

What deal does Trump want Cuba to make?

The Trump administration has outlined a set of demands that would serve as the foundation for any sanctions relief or energy deal with Cuba. These center on political prisoners, economic reforms, property compensation, and broader human rights commitments—the same broad framework that has underpinned American policy toward Havana for decades.

Ultimatum details

Trump’s executive order at the end of January 2026 threatened tariffs against countries supplying Cuba with petroleum, effectively weaponizing the embargo into a secondary pressure tool against third parties. The administration declared a national emergency citing an “unusual and extraordinary threat” to U.S. national security and foreign policy.

Potential terms

U.S. officials have urged Cuban leaders to release prisoners, pursue market reforms, and provide compensation to owners of properties nationalized after the 1959 revolution. In exchange, Cuba has indicated openness to negotiating on prisoner releases and market reforms—while pushing for oil exploration opportunities, infrastructure investments, partial sanctions relief, and greater law enforcement cooperation.

U.S. officials gave Cuba a two-week deadline to release high-profile political prisoners including Luis Manuel Otero Alcantara and Maykel Osorbo of the San Isidro Movement. Cuba, for its part, has urged lifting the energy blockade, calling it “economic coercion” and “unjustified punishment of the entire Cuban population.” To better understand the ultimatum, read this article on the significat d’aquesta frase.

Skip York, a global energy expert at Rice University’s Baker Institute for Public Policy, assessed that the fuel situation in Cuba will get “pretty dire pretty fast” given the supply disruptions. The State Department’s position remains firm: diplomatic solution preferred, but collapse is not acceptable.

What did experts say?

Fuel situation in Cuba will get pretty dire pretty fast.

Skip York, Global Energy Expert, Rice University’s Baker Institute for Public Policy

President Trump is committed to a diplomatic solution, but will not let the island collapse into a major national security threat.

State Department Official (via Responsible Statecraft)

John Kavulich, president of the U.S.-Cuba Trade and Economic Council, suggested that Steve Witkoff and Jared Kushner may be positioned to negotiate a deal with the Cuban government if formal diplomatic channels produce results. Whether the administration puts those senior figures forward remains to be seen.

The U.S. has seized control of Venezuela’s oil production following the leadership transition there. That gives Washington enormous leverage—potentially enough to force Havana’s hand on almost anything. But it also creates a humanitarian catastrophe risk that even the Trump administration seems keen to avoid, as evidenced by the late March 2026 decision to allow a Russian crude oil tanker to reach Havana. Whether that brief easing of pressure marks a shift in strategy or simply reflects internal administration divisions remains unclear.

For Havana’s leaders, the calculus is brutal: agree to American demands and risk appearing to capitulate, or hold firm and watch the electric grid fail, hospitals go dark, and streets fill with garbage. Trump, meanwhile, has publicly predicted the island will “fall pretty soon”—but he’s also insisted a deal could happen quickly if Cuba chooses differently.

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Trump’s stark ultimatum arrives amid a Cuba tourism fuel shortage that has crippled the island’s economy and stranded visitors due to sanctions and grid failures.