In this episode, Alex looks at how President Trump’s success in Venezuela appears to have emboldened him to think bigger—and riskier. Trump has revived his push to take Greenland, framing it as a strategic necessity and alarming Denmark and other NATO allies, who warn that a U.S. move against a fellow member’s territory could effectively collapse the alliance.

At the same time, the fallout from Venezuela is hitting Cuba hard. With Venezuelan oil cut off, Havana is facing a severe economic crisis, and Trump allies are openly suggesting the island is “ready to fall.” Together, these developments raise a central question: is this a new era of American assertiveness—or a destabilizing gamble that could upend NATO and reshape the global order?