Trump's Cuba policy targets regime's 6-decade influence machine

Trump's push to end communist rule in Cuba confronts a regime that has spent six decades cultivating influence among Western elites.

President Trump's Cuba policy marks the first sustained US effort to dismantle the Castro regime's influence network, targeting not just Havana's military conglomerate but the progressive intellectuals and institutions that have shielded it for six decades.

"The dictatorship's greatest foreign-policy successes have been in the salons of Washington, Ottawa and Madrid," Martín Rodríguez y Rodríguez wrote in a Wall Street Journal letter, arguing the regime has sold "repression as sovereignty, economic failure as anti-imperial resistance, and one-party rule as social justice."

The administration has indicted former President Raul Castro for the 1996 shootdown of two civilian aircraft that killed four US citizens, designated GAESA — the military conglomerate controlling roughly 70 percent of the Cuban economy — and reinstated Title III of the LIBERTAD Act, enabling lawsuits over confiscated property. The Treasury Department's Office of Foreign Assets Control issued administrative subpoenas to streamer Hasan Piker, CODEPINK co-founder Medea Benjamin and about 40 others who traveled to Cuba in March on a humanitarian mission, according to a Fox News report.

The outcome will determine whether the US can sustain pressure on a regime that has outlasted 11 American presidents since the 1960 embargo. With an estimated 2 million Cubans having fled the island in the past five years and the economy crippled by blackouts and fuel shortages, the question is whether diplomatic isolation or economic engagement will prove more effective in driving change.

The administration's approach builds on the playbook used in Venezuela, where US special operators captured Nicolas Maduro in a January raid that lasted two hours and 28 minutes. Secretary of State Marco Rubio, a Cuban American who has advocated for hardline policies toward Havana, has framed the Cuba push as a natural extension. "Currently, the only thing standing in the way of a better future are those who control your country," Rubio told the Cuban population in a Spanish-language video released on independence day.

The last time the US pursued a similar escalation was in 1996, when President Bill Clinton signed the Helms-Burton Act after the regime shot down two Brothers to the Rescue aircraft, killing four American citizens. That law codified the embargo but was never fully enforced. Trump's reinstatement of Title III marks the first time private lawsuits against entities trafficking in confiscated Cuban property have been permitted since the law's passage.

The influence network under pressure

The OFAC subpoenas represent a new front in the administration's campaign — targeting Americans who provide material support to the Cuban government. The investigation focuses on whether Piker, Benjamin and others violated US sanctions by traveling to Cuba on humanitarian visas and delivering medical supplies to pediatric hospitals. Benjamin responded by saying the administration was investigating her for trying to "help save babies," while Piker called the probe an attack on the First Amendment.

Critics argue the approach risks repeating the failures of the 66-year embargo, which most foreign policy experts agree has failed to dislodge the Castro regime while imposing severe economic hardship on ordinary Cubans. Bill Press, a former CNN host, wrote in The Hill that "any war against Cuba would be another pure folly" and called for ending the embargo instead, arguing that unleashing American enterprise would do more to drive change than military pressure.

Cubans themselves are divided. Some, like engineer Ivan Luis Arcia, told the Christian Science Monitor they have "hopes pinned on Trump" for change. Others, like Havana resident Sheila Rivero, said they fear "a bombardment could break out here, ultimately claiming the lives of innocent people."

The administration shows no signs of backing down. With Raul Castro indicted, GAESA designated and the OFAC investigation underway, Trump has positioned himself as the first US president to treat the Castro regime as an active threat rather than a Cold War relic. Whether that strategy succeeds where 11 predecessors failed will depend on whether the regime's six-decade network of influence can withstand sustained pressure from Washington.

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