Trump’s Cuba Gambit › American Greatness
Fred Fleitz
May 22, 2026
Trump’s Cuba strategy combines economic pressure, targeted humanitarian aid, and direct outreach to Cubans to weaken the regime—not invasion or appeasement.
A few weeks ago, the mainstream media was in full panic mode, warning that President Trump was planning to invade Cuba. These claims were overheated and completely off base. President Trump has unveiled a far grander and more sophisticated strategy—one that combines relentless economic pressure with targeted humanitarian assistance and a direct appeal to the Cuban people. It is a high-stakes gamble by Trump and Secretary of State Marco Rubio, but one well worth taking.
The first pillar is maximum economic pressure. The administration has strangled the island’s economy and starved it of energy. After the U.S. helped topple Venezuela’s Nicolás Maduro, the subsidized oil lifeline that kept Cuba’s lights on was severed. Trump’s January executive order declared a national emergency and imposed tariffs on any country shipping oil to Cuba. The results have been dramatic and painful: nationwide blackouts lasting up to 22 hours a day, collapsing hospitals, shuttered businesses, and economic collapse.
This outcome was the logical result of decades of Cuban mismanagement, finally encountering an American president who refuses to subsidize it. The regime’s military conglomerate, GAESA—founded by Raúl Castro and controlling the lion’s share of the economy—has hoarded billions while ordinary Cubans suffer. Trump’s Cuba policy stops America from papering over this corruption.
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https://amgreatness.com/2026/05/22/trumps-cuba-gambit/
