U.S. Cuba Policy Faces Complex Challenges, Analyst Says

The Trump administration is weighing its next moves regarding Cuba following recent diplomatic focus on Iran, according to analysis provided by Wall Street Journal columnist and historian Walter Russell Mead.

Mead emphasized that while significant changes could be on the horizon—including potential appointments of a new Treasury Secretary and Central Bank leadership—the path forward remains complicated. “A lot could happen, but it’s going to be complicated,” Mead stated, noting that Cuba faces severe economic difficulties distinct from Venezuela’s crisis. While Venezuela possesses oil resources, Cuba lacks comparable assets, making its economic recovery more challenging.

According to Mead, achieving prosperity and stability in Cuba will require substantial effort from the U.S. government to identify viable pathways forward. He highlighted the potential role of successful Cuban-Americans based in Miami and Madrid, who possess both capital and business expertise. However, their investment would depend on the Cuban government implementing deep reforms that provide confidence and legal security for diaspora investors.

Significant legal obstacles remain, Mead explained. U.S. law stipulates that property confiscated under Fidel Castro’s regime should be returned to original owners, yet determining clear ownership titles in Cuba today presents considerable bureaucratic complexity. “It can be a big bureaucratic hassle to try to sort this thing out,” Mead noted, adding that mechanisms must be developed to facilitate investment even while some property questions remain unresolved.

When asked about the current regime’s flexibility, Mead pointed to historical context: Cuban leadership has resisted U.S. overtures since the Eisenhower and Kennedy administrations, including during the Bay of Pigs era. While the country is now in a “deep hole” economically, Mead characterized the Cuban Communist Party and military as notably resilient—”a lot tougher than the Venezuelans.” He referenced how Venezuelan authorities previously relied on Cuban personnel for security operations when local resources proved insufficient.

Mead acknowledged Cuba’s dire economic situation, including reported U.S. restrictions on oil supplies, but drew a parallel to North Korea’s endurance during the pandemic. Despite severe hardship and isolation, the North Korean regime maintained its course, demonstrating that sanctions alone do not guarantee political change. However, Mead distinguished Cuba’s situation, noting that the Castro leadership does not wield the same absolute control as North Korea’s Kim dynasty and cannot as easily disregard widespread hunger and public discontent.

Having visited Cuba frequently during the 1990s, Mead expressed personal support for constructive change. “I want this to work. I think it’s better for us, it’s better for them,” he said. He welcomed the Trump administration’s active engagement with Cuba policy rather than allowing the situation to deteriorate unaddressed.

Still, Mead cautioned that progress demands sustained effort. “It’s going to take a lot of work and a lot of skull sweat to get us from where we are to where we need to be,” he concluded, expressing hope that U.S. policymakers would navigate the complexities successfully.