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The Cuban government failed to implement necessary economic reforms during the 'Obama window' of opportunity, leaving the economy fragile and far more susceptible to the subsequent 'maximum pressure' campaign from the U.S.

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An expert assesses a 70-80% probability that Cuba will cut a deal with the Trump administration, similar to Venezuela's. Lacking a foreign patron like the USSR or Chavez-era Venezuela, the Cuban regime is motivated by economic desperation to make a pragmatic deal, trading alignment for relief from US sanctions to maintain power.

Private small and medium-sized businesses, legalized in 2021, have become vital for Cubans' survival, paying up to 10 times state salaries. However, the Communist Party remains ambivalent, creating a climate of legal uncertainty for entrepreneurs who are essential to the economy.

Despite a strong sense of nationalism, suffering in Cuba has become so profound that many citizens now see American intervention as the only path to change. Their desperation for a resolution outweighs their historical opposition to foreign involvement, viewing it as a "get it over and done with" scenario.

Despite facing extreme economic scarcity, crippling power outages, and decades of US pressure, the Cuban government's collapse is not imminent. Analysts warn against underestimating the regime's staying power, citing its highly disciplined organization and a core of revolutionaries who have defied predictions of their demise.

A decade ago, regional solidarity pressured the U.S. to normalize relations. Today, Latin America is fragmented, and many leaders see Cuba's crisis as its own fault, removing a key diplomatic lever that existed during the Obama era.

The goal was to give Cubans a taste of economic freedom and normality, creating internal pressure for change that would overwhelm the government's capacity to control the pace of reform. It was a strategy of 'corrosive normality'.

By refusing to bend to pressure, the Cuban government forces the US into a difficult position: either back down or escalate to a full-scale invasion, a politically unpalatable option the US wants to avoid.

By crippling the Cuban government's ability to operate, US sanctions are forcing the regime to cede control of key sectors. For example, the state has had to hand off its monopoly on importing oil, allowing private businesses to import it for their own needs—an ironic push towards a free-market principle.

The DSA's support for Cuba's regime perpetuates a narrative that U.S. sanctions are the sole cause of its struggles. This overlooks the historical fact that Cuba's vibrant economy collapsed following Castro's disastrous policy of forcing the entire nation into sugar production, which destroyed other industries.

The complex, codified U.S. sanctions regime prevents the use of traditional economic and development tools that would be essential to support a successful reform process in Cuba, creating a self-defeating policy paradox.