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.

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 US strategy in Cuba may not be to oust the Castro family entirely, but to replace the current president while leaving the core power structure and even Castro relatives intact. This mirrors the approach in Venezuela, suggesting a pragmatic rather than purely ideological goal.

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.

Instead of traditional regime change, current U.S. strategy focuses on 'conversion.' This involves creating such favorable economic and diplomatic conditions for adversaries that abandoning hostile ideologies becomes their only rational choice.