Cuba Is Next: The 125-Year Obsession America Can't Quit

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 and a personal vendetta shaping US foreign policy in real time. Someone just dropped $57,000 on a prediction market betting it all goes hot before the end of 2026.

Tio Raul is powered by Maneku — the AI built for real conversations. Learn more at maneku.ai

TIMESTAMPS:

00:00 – Knicks Win & the Puerto Rican Connection

02:30 – More Puerto Ricans in Florida Than New York?

05:00 – Bad Bunny, Nuyoricans & José Alvarado

08:15 – Cuba: Spain's Prize Colony & the First Concentration Camps

14:30 – The USS Maine, Yellow Press & the Spanish-American War

19:45 – The Platt Amendment: Independence with an Asterisk