Cuba faces economic collapse with dwindling oil reserves, prompting the Castro regime to negotiate with the Trump administration. Despite Cuba's weak position, the White House has dropped meaningful political change as an objective. Recent reports indicate the Trump administration seeks removal of President Miguel Díaz-Canel as a condition for economic negotiations, potentially allowing the military to consolidate power while offering superficial gestures like limited prisoner releases and diaspora investment permissions.

Such a deal would not represent substantive political opening but rather economic concessions for regime survival. The Cuban military already controls enterprises involving foreign investments, tourism, retail, and professional services exports. U.S. investment without verifiable political reforms risks strengthening the military's economic control, with dollars flowing directly into military-managed enterprises rather than fostering genuine market transformation or private sector development.

The author recommends conditioning U.S. investment on stripping the military from economic management and establishing transparent business practices. Accepting a deal without these safeguards would signal to Cuban Americans their political support doesn't matter and to Cubans on the island that their aspirations can be traded. Any economic agreement must address both immediate market opportunities and long-term democratic reforms to benefit all stakeholders and avoid repeating Venezuela's experience with U.S.-backed regime changes.