June 25, 2026

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

1 hour 46 minutes

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

...more