While dozens of major companies flee Cuba under President Donald Trump-era sanctions, a select group of insiders with ties to the president are quietly positioning themselves to scoop up the island's assets, according to the Guardian.
That includes executives working for the Trump Organization.
Spanish hotel giants Meliá and Iberostar, Canadian mining firm Sherritt International, European shipping companies, and even Visa and Mastercard have all pulled out of Cuba this summer, spooked by sweeping new secondary sanctions tied to Trump's pressure campaign following the ouster of Venezuelan President Nicolás Maduro. Secretary of State Marco Rubio told Axios last month there are "no escape valves" left for the island.
But the Guardian reports a different story is playing out behind the scenes.
"A growing cast of Washington and Florida insiders – from billionaire Trump cronies and Rubio-linked lobbyists to Cuban exiles – are jockeying for control of the communist-ruled island-nation’s key assets, charging top dollar to help clients navigate the ever-expanding web of sanctions, and positioning themselves for lucrative business opportunities in the case of regime collapse," the Guardian's Lee Schlenker and Ed Augustin reported.
The Guardian report added that, "several Trump Organization executives who had previously traveled to the island to explore real estate deals and who even registered the Trump trademark there in 2008 have in recent months returned to Cuba under the aegis of Dominari Holdings for meetings."
Meanwhile, ordinary Cubans have endured a fuel blockade since January, after the administration cut off oil shipments from Venezuela and pressured Mexico into halting its own deliveries. Yet Treasury-authorized fuel exports from Florida and Texas to Cuba's private sector have surged past $160 million this year, up from almost nothing in 2025.
"If I had done during the Biden administration what Trump's friends have done now, I'd have been put in jail," said one longtime Cuba policy expert, granted anonymity to speak candidly.