Trump Administration Eyes Cuba After Maduro’s Ouster, Seeks Insider Deal

Key Facts

Published: January 22, 2026 Location: Washington D.C. Source: Wall Street Journal

• Trump administration believes Cuba’s economy is near collapse after losing Venezuelan oil support and is quietly seeking an insider deal to end Communist rule
• President Donald Trump is using the Maduro ouster as both a blueprint and warning, signaling pressure while offering Havana a last-chance off-ramp
• Cuba’s leadership rejects negotiations as shortages, blackouts, and unrest grow, with U.S. officials warning the regime is more fragile than at any time in decades

by Emmitt Barry, Worthy News Washington D.C. Bureau Chief

WASHINGTON D.C. (Worthy News) – Emboldened by the U.S.-backed removal of Venezuelan leader Nicolás Maduro, the Trump administration is quietly searching for Cuban government insiders willing to cut a deal that could end Communist rule on the island by year’s end, according to a Wall Street Journal exclusive.

Senior U.S. officials believe Cuba’s economy is nearing collapse after losing subsidized oil from Venezuela, a lifeline that has propped up Havana for decades. President Donald Trump has publicly warned Cuban leaders to “make a deal before it’s too late,” vowing to cut off remaining financial and energy support.

Administration officials say the January U.S. raid that captured Maduro — aided by an insider — is being used as both a blueprint and an implicit warning to Havana. While no military action against Cuba has been announced, U.S. intelligence assessments describe severe shortages, blackouts, and the possibility that the island could run out of oil within weeks.

The White House is also targeting Cuba’s overseas medical missions, a key source of hard currency, through visa bans and diplomatic pressure. Secretary of State Marco Rubio, whose family fled Cuba in the 1950s, has long supported ending Communist rule there.

Cuba’s leadership, dominated by former ruler Raúl Castro and current President Miguel Díaz-Canel, has rejected U.S. pressure, insisting it will not negotiate under coercion. Meanwhile, allies Russia and China have pledged fresh support to Havana.

Despite decades of sanctions and isolation, U.S. officials now see Cuba as more vulnerable than at any point in nearly 70 years — but acknowledge there is no clear plan yet for who or what would replace the current regime.

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