What Trump likely wants is a deal, one that opens Cuba to US investment and tourism, and lets him claim a historic win. The problem is that Cuba has no meaningful political opposition to replace the Castro government, and no equivalent of Venezuela's Delcy Rodriguez waiting in the wings.
A purely economic deal may seem like the easy path forward, but it risks disappointing Cuban American voters who were heavily invested in Trump's 2024 election, and putting Secretary of State Marco Rubio in an impossible position with his own community. As Bustamante puts it, Cuba is attractive to Trump "not because of natural resource wealth" but because of "the symbolism of communism, and being able to say that we planted the flag and defeated that thing that no one else could."
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