Cuba’s Rebuilding Efforts Likely to Be ‘Fits and Starts’ as Trump Signals Military Action

By Jim Mishler | Wednesday, May 27, 2026

Republican strategist John Jordan said Cuba’s rebuilding effort will appear disjointed due to years of deterioration under communist rule.

Jordan described the process as “fits and starts,” noting significant borrowing and public debt would be necessary. He identified critical elements for immediate attention: commercial enterprise, a stable legal system, court systems, rule of law, contract enforcement, and securities laws.

Jordan stressed these are essential for investors to understand the environment before committing resources. “So that companies can go in there,” he said. “They can invest. They can employ Cubans.”

He emphasized a large number of Cubans have fled the island nation but are eager to return and assist with reconstruction. Jordan also highlighted the need for a government that respects citizens’ rights—a development currently underway in Venezuela—to encourage investment.

Additionally, he called attention to Chinese listening stations and Russian intelligence operations within Cuba.

President Donald Trump and Secretary of State Marco Rubio recently raised the prospect of U.S. military intervention in Cuba following the administration’s announcement of criminal charges against former Cuban leader Raul Castro. Trump stated previous U.S. presidents had considered intervening in Cuba for decades but said, “it looks like I’ll be the one that does it.”

Rubio separately told reporters Cuba has been a national security threat for years due to its ties with adversaries and that Trump is determined to address it.