U.S. President Donald Trump wearing a "happy Trump" pin speaks during a meeting with oil industry executives at the White House in Washington, D.C., U.S., January 9, 2026. REUTERS/Kevin Lamarque
Riding high after the dramatic ouster of Venezuelan strongman Nicolás Maduro, the Trump administration is now zeroing in on Cuba, hunting for government insiders willing to cut a deal and help dismantle the Communist regime by the end of the year.
That's according to exclusive reporting in the Wall Street Journal, which said administration officials believe Cuba's economy is teetering on the brink of collapse after losing its vital Venezuelan oil lifeline.
"I strongly suggest they make a deal. BEFORE IT IS TOO LATE," President Donald Trump warned in a Jan. 11 Truth Social post, threatening "NO MORE OIL OR MONEY" to the island nation.
The Trump team is holding meetings with Cuban exiles and civic groups in Miami and Washington, searching for somebody inside Havana's government who might see the writing on the wall. The brazen Jan. 3 military raid that captured Maduro — which killed 32 Cuban soldiers and intelligence operatives— is being used as an implicit warning to Cuba's leaders about what's to come if they don't negotiate.
U.S. intelligence painted a bleak picture of Cuba's economy, with chronic shortages of basic goods, medicines, and rolling blackouts. With Venezuelan oil supplies drying up, economists warn Cuba could run out of fuel within weeks. The administration is also targeting Cuba's overseas medical missions, the regime's most important cash source, through visa bans.
For Trump and his Florida-tied inner circle, including Secretary of State Marco Rubio, son of Cuban immigrants, toppling Cuba's regime represents a defining legacy moment. Yet experts warn the Venezuela playbook may not work in Cuba's single-party Stalinist state, where civil society barely exists, and no opposition movement stands ready.