250th America’s Manifest Destiny: Harrisburg to Havana episode artwork

EPISODE · May 19, 2026 · 2H 3M

250th America’s Manifest Destiny: Harrisburg to Havana

from The Wake Up America show with Austin Petersen · host wakeupamericashow

We mark the 250th anniversary by reading the parts of the Declaration nobody puts on the merch -- Jefferson's criminal charges against a king who blocked western settlement, strangled immigration, and held land promises over men who had bled for them. Then we turn to Cuba, where classified intel says the island has acquired 300+ military drones from Russia and Iran. We go back to the Bay of Pigs to establish the one rule that covers everything that comes next: half measures are always wrong. And we close with the hardest question in the room -- if the Castro regime falls, can the Cubans still on the island actually govern themselves, or does the best argument for a free Cuba walk around Miami? Plus the prediction market corruption story for what it actually is -- not a technology problem, but the oldest compensation trap in the republic. 🇺🇸 A1 -- Jefferson's grievance, the Proclamation of 1763, and the manifest destiny already baked into the founding documents ⚔️ A2 -- Bay of Pigs, the half-measure doctrine, Cuba's drone arsenal, and the statehood question Washington isn't ready to ask 🎙️ B1 -- Jon Miltimore on prediction markets, insider trading, and why Polymarket didn't invent the corruption 🇨🇺 B2 -- Mailyn Salabarria on growing up inside Castro's Cuba and whether a free Cuba can govern itself GUESTS THIS EPISODE 🎙️ Jon Miltimore -- Senior Editor, American Institute for Economic Research | @miltimore79 🇨🇺 Mailyn Salabarria -- Speaker, The Dissident Project | @MailynSpeaks 4LibertyShop.com expatmoney.com/AUSTIN 4libertynetwork.com wakeupamericashow.com/support #WakeUpAmerica #Cuba #BayOfPigs #DeclarationOfIndependence #America250 #ManifestDestiny #PredictionMarkets #Polymarket #Kalshi #InsiderTrading #Libertarian #AustinPetersen #Rumble

We mark the 250th anniversary by reading the parts of the Declaration nobody puts on the merch -- Jefferson's criminal charges against a king who blocked western settlement, strangled immigration, and held land promises over men who had bled for them. Then we turn to Cuba, where classified intel says the island has acquired 300+ military drones from Russia and Iran. We go back to the Bay of Pigs to establish the one rule that covers everything that comes next: half measures are always wrong. And we close with the hardest question in the room -- if the Castro regime falls, can the Cubans still on the island actually govern themselves, or does the best argument for a free Cuba walk around Miami? Plus the prediction market corruption story for what it actually is -- not a technology problem, but the oldest compensation trap in the republic.🇺🇸 A1 -- Jefferson's grievance, the Proclamation of 1763, and the manifest destiny already baked into the founding documents ⚔️ A2 -- Bay of Pigs, the half-measure doctrine, Cuba's drone arsenal, and the statehood question Washington isn't ready to ask 🎙️ B1 -- Jon Miltimore on prediction markets, insider trading, and why Polymarket didn't invent the corruption 🇨🇺 B2 -- Mailyn Salabarria on growing up inside Castro's Cuba and whether a free Cuba can govern itselfGUESTS THIS EPISODE 🎙️ Jon Miltimore -- Senior Editor, American Institute for Economic Research | @miltimore79 🇨🇺 Mailyn Salabarria -- Speaker, The Dissident Project | @MailynSpeaks4LibertyShop.com expatmoney.com/AUSTIN 4libertynetwork.com wakeupamericashow.com/support#WakeUpAmerica #Cuba #BayOfPigs #DeclarationOfIndependence #America250 #ManifestDestiny #PredictionMarkets #Polymarket #Kalshi #InsiderTrading #Libertarian #AustinPetersen #Rumble

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250th America’s Manifest Destiny: Harrisburg to Havana

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This episode was published on May 19, 2026.

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We mark the 250th anniversary by reading the parts of the Declaration nobody puts on the merch -- Jefferson's criminal charges against a king who blocked western settlement, strangled immigration, and held land promises over men who had bled for...

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