About this episode

The episode explores America's long-standing obsession with Cuba, covering historical events and figures that shaped the relationship.

The Knicks just won the NBA Finals — and José Alvarado led the Puerto Rican Day Parade the next morning. But while New York was celebrating, something else was quietly happening in the Caribbean: a US carrier strike group just parked itself 90 miles from Havana. Henry and Danny — with help from AI guest Tio Raul — break down the full arc of America's 125-year obsession with Cuba. From the first concentration camps in history, to the mob-run casino island Batista built for American business, to Fidel's guerrilla campaign on a 10-person yacht with 81 men aboard, to the Cuban tank crews that went and fought Israel on a mountain in Syria — this island punches so far above its weight it's almost unbelievable. They also get into why Cuba deployed nearly half a million troops to Angola over 16 years, how that campaign helped end apartheid in South Africa (and what Nelson Mandela himself said about it), and how Aroldis Chapman — the hardest thrower in baseball history — had to buy his freedom from a cartel for $30 million just to pitch in the majors. And then there's Marco Rubio, whose family left Cuba under Batista — not Castro — now sitting as Secretary of State with a carrier fleet…

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