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 24:00 – Batista, the American Mob & Meyer Lansky's Havana 29:00 – Castro, the Granma & the 26th of July Movement 33:30 – Bay of Pigs: The CIA's Most Embarrassing Failure 38:00 – The Cuban Missile Crisis & Proletarian Internationalism 44:00 – Cuba vs. the IDF: Tank Crews in the Golan Heights 48:00 – Operation Carlota: Cuba Ends Apartheid in Angola 57:00 – Chapman, Cartels & Cuban Athletes Buying Their Freedom 01:04:00 – The Soviet Collapse & Cuba's "Special Period" 01:07:00 – Mariel Boatlift, Scarface & the Cuban American Political Machine 01:14:00 – Obama Normalizes, Trump Reverses, Rinse, Repeat 01:22:00 – Marco Rubio's Messy Timeline & the Carrier in the Caribbean 01:35:00 – Should the US Invade Cuba? Prediction Markets Say… 01:42:00 – Final Thoughts #CubaHistory #USForeignPolicy #MarcoRubio #ColdWarHistory #BayOfPigs #BroHistory #Podcast #FidelCastro #Knicks #PuertoRico #JoseAlvarado #AroldisChapman #Angola #Apartheid #LatinAmerica #Geopolitics #TioRaul #Maneku Links to our other stuff on the interwebs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.youtube.com/@BroHistory⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://brohistory.substack.com/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ #348 Learn more about your ad choices. Visit megaphone.fm/adchoices