The Dispatch Podcast How Far Will Trump Go in Cuba?
35 snips
Mar 31, 2026 
Megan McArdle, pragmatic policy columnist; Kevin Williamson, sardonic conservative commentator; Gil Guerra, Latin America expert with on-the-ground Cuba knowledge. They unpack nationwide blackouts, Russia’s fuel deliveries, U.S. options for pressuring Havana, prospects for regime change, diaspora and market roles in a transition, and how race, inequality, and geostrategic rivals shape Cuba’s future.
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Sanctions Without A Plan Rarely Topple Regimes
- Sanctions and embargoes rarely force regime change alone; they inflict suffering but need complementary political alternatives to succeed.
- Kevin Williamson argues U.S. unwillingness to provide the follow-up makes pressure less effective historically.
Plan For Postregime Chaos Not Instant Democracy
- Avoid assuming a collapsed Cuban regime would yield easy democratic reconstruction; plan for governance, refugee flows, and instability.
- Megan McArdle warns decades of socialism erase institutional memory, making post-collapse rebuilding resemble Russia more than Poland.
Pressure Aims To Cut Cuba's Regional Leverage
- Cuba hawks argue pressure aims to sever Cuba's role as an external sponsor and stop its influence in Latin America.
- Gil notes China's and Russia's growing ties and Cuba's export of security services to regimes like Venezuela.
