Will Trump’s Pressure Campaign Bring Cuba to the Table?

Will Trump’s Pressure Campaign Bring Cuba to the Table?
People walk down a street during a blackout in Havana, Cuba, Sept. 10, 2025 (AP photo by Ramon Espinosa).

In late January, The Wall Street Journal reported that U.S. President Donald Trump’s administration believes it can force regime change in Cuba before the end of this year. As part of that effort, Trump signed an executive order last week imposing tariffs on goods from countries that sell or give oil to Cuba. With fewer than three weeks of oil supplies on the island and only one small shipment of it received in the past 30 days, Cuba may completely run out of fuel by the end of the month. Given that the country’s electrical grid depends on oil, the new U.S. pressure campaign will likely force nationwide brownouts and blackouts by the end of February. The question is: What then?

Economic pressure by the U.S. against the Cuban government is far from new. The United States has maintained some form of sanctions on Cuba since the 1960s. That makes U.S. policy the modern world’s longest-running case study demonstrating that economic coercion alone cannot force regime change. However, there is a belief in Washington that because Cuba has no remaining allies to help it evade or counter the sanctions, this time may be different.

Since the 1960s, Cuba’s political and economic survival has almost always depended on an allied foreign power. For most of the Cold War, that ally was the Soviet Union. Following the fall of the USSR, Cuba went through an incredibly difficult economic crisis called the “Special Period,” in which much of the island’s population suffered due to a lack of food and other basic needs. Nevertheless, the political regime didn’t crumble. To the contrary, by the late 1990s, Cuba had implemented a few economic reforms and attracted investment from European countries, which eased the pain.

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