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Hello Reader,
Three ruthless tyrannies teeter simultaneously. Tens of thousands of Iranians lie dead or injured from this month's massacres. Venezuelans scavenge for food in what was once Latin America's richest nation. Cuba nears total collapse.
This is the greatest opportunity for global freedom since 1989.
This newsletter's Friday format continues to evolve—it will return to domestic stories next week, alongside familiar features like Freedom Fighter of the Week, American Renegade of the Week, and "Counterstrikes", which combats misleading media narratives with deeper insights.
But this moment demands we confront the unspeakable question: when is regime change justified, and if pursued, how can we ensure it succeeds?
Regime Change: From Ajax to Absolute Resolve
Kermit Roosevelt slipped into Tehran in the summer of 1953 disguised as a tourist, carrying a million dollars in cash and orders to topple a government. The grandson of Theodore Roosevelt spent weeks in safehouses coordinating with MI6, bribing clerics, enlisting military officers, and hiring street thugs. The target: Prime Minister Mohammad Mossadegh, who had committed the unforgivable sin of nationalizing Iran’s oil industry, wresting it from British Petroleum's clutches.
On August 19th, paid mobs surged through Tehran's streets. Soldiers stormed Mossadegh's residence as the democratically elected prime minister refused the Shah's order to step down. Within hours, it was over. Mossadegh spent the rest of his life under house arrest, and the Shah's brutal SAVAK police state took root. 26 years later, that oppression exploded into revolution—and Ayatollah Khomeini seized power.
The coup wasn't purely American imperialism crushing Iranian democracy—Mossadegh faced domestic opposition from clerics who viewed his secularism as threatening Islam. But the intervention backfired catastrophically because Washington chose the short-term stability of a dictator over allowing Iranians to resolve their own tensions. That choice fueled 26 years of torture chambers, the "Great Satan" epithet, and ultimately the Islamic Republic that torments Iran to this day.
The Unspeakable Question
For over two decades, "regime change" has been politically radioactive—what many call "The Iraq Syndrome." This is where the pacifist left and MAGA-isolationist right find common ground—both reject regime change and nation-building as imperial follies doomed to fail.
But on June 22nd, 2025, Trump shattered the consensus: "It's not politically correct to use the term, 'Regime Change,' but if the current Iranian regime is unable to MAKE IRAN GREAT AGAIN, why wouldn't there be a regime change???" Now, the administration openly pursues regime change in Cuba.
The question signaled a profound shift—Trump breaking from over two decades of post-Iraq orthodoxy and his own isolationist base. The tension now fractures his administration. JD Vance advocates negotiating with Iran. Stephen Miller champions working with whomever secures American interests—the will of the people be damned. Secretary of State Marco Rubio consistently grasps what history teaches—and Trump, in his coherent moments, seems to agree: sometimes tyranny must be confronted.
Three regimes teeter simultaneously—the greatest opportunity to advance global freedom and liberate tens of millions from tyranny in over a generation.
Is regime change justified to achieve it?
Lessons in Blood
America's past attempts at regime change offer lessons in blood, purchased at the cost of American soldiers' lives. These deaths teach what regime change requires—and what guarantees catastrophe.
Japan stands alone as America's most successful regime change—total military defeat followed by seven years of occupation allowed MacArthur to build democratic institutions from scratch. But Americans won't support prolonged occupation absent direct threat and declared war.
History offers brutal lessons on what justifies intervention.
Eisenhower's 1954 Guatemala coup toppled Jacobo Árbenz to protect United Fruit's banana plantations—pursuing resources without genuine security threats. Result: 36 years of civil war killing 200,000. Kennedy's 1961 Bay of Pigs invasion failed because Cubans supported Castro—without public support, intervention becomes invasion. Kennedy and Nixon's Vietnam quagmire toppled Diem, creating political chaos demanding deeper intervention that killed 58,000 Americans.
Nixon's 1973 Chile coup installed Pinochet, who murdered 3,000 and tortured 38,000—pursuing stability through autocracy. But Reagan's George Shultz recognized that propping up dictators threatened long-term interests. The U.S. supported the 1988 "No" campaign that delivered enduring Chilean democracy. Reagan's 1983 Grenada invasion succeeded because the population demanded it and the U.S. committed to democratic institution building.
Bush's 2003 Iraq de-Baathification purged 385,000 military members and 30,000 government officials, creating insurgents who spawned ISIS.
The pattern is unmistakable. Interventions pursuing resources or stability through autocrats fail. Interventions without public support fail. Interventions that fail to secure military support fail.
History demands four criteria:
1. Direct threat to American security or regional threats imperiling allied democracies.
2. Broad citizen and regional support—the population must demand change.
3. An inflection point creating genuine opportunity to grant freedom and transform lives
4. Significant support from military or security apparatus—the opposition must secure the guns.
Without all four, regime change becomes imperialism. With all four, it becomes liberation.
The Strategic Threats
America's Cold War sins—Mossadegh, Latin American coups, Vietnam—were committed in pursuit of defeating Communism, the gravest threat to humanity in the 20th century. One estimate puts the ideology's death toll at 100 million people across the globe.
That's what Eisenhower faced in 1953 when he confronted Mossadegh. Although he was not a Communist, U.S. policymakers feared we could not control their influence.
Today, Trump confronts a less monolithic, but very real threat—an authoritarian axis seeking to overturn the liberal world order and export an inherently tyrannical governance model: China, Russia, North Korea, Iran, and to a lesser extent, Venezuela and Cuba.
Iran's 47-year war against America began with 444 days of hostages in Tehran and escalated through decades of proxy terrorism—from Beirut's Marine barracks to Iranian IEDs killing hundreds of U.S. troops in Iraq. Tehran fueled Assad's slaughter in Syria that killed 500,000. Iran fires on American forces through Iraqi militias, disrupts global shipping through Houthis, and supplies Russia with the drones that kill Ukrainian thousands of innocent civilians.
Cuba hosts Russian intelligence services and welcomed Chinese delegations this week pledging $80 million in aid—Beijing's latest investment in a Western Hemisphere outpost 90 miles from Florida. 32 Cuban soldiers and intelligence operatives died in Caracas protecting Maduro on January 3rd.
Venezuela's collapse under Maduro triggered 8 million refugees destabilizing Colombia, Ecuador, Peru, and Chile—the Western Hemisphere's worst migration crisis. The regime kept Cuba's lights on through subsidized oil shipments while hosting Chinese military installations, including electronic intelligence facilities monitoring U.S. communications.
Popular Support
Over 16,000 Iranians lie dead from this month's massacres—shot in the back while fleeing, bodies floating in rivers. After 47 years of theocratic oppression, Iranians are willing to die for their freedom.
Venezuelans already voted overwhelmingly for regime change: Edmundo González won 70%, risking colectivo militia violence to demand freedom. A majority of South Americans endorsed Trump’s Caracas raid—a higher rate than Americans themselves.
Cuba's 2021 protests saw tens of thousands take to the streets across the island demanding "Libertad" and an end to the dictatorship—the largest demonstrations since the revolution. The regime crushed them through systematic repression and now holds over 1,000 political prisoners.
Two Nobel Peace Prize winners—Shirin Ebadi (Iran) and María Corina Machado (Venezuela)—now call for regime change in their respective countries. When even Nobel Peace laureates advocate for military strikes, it speaks to their people's desperation.
Inflection Points
The suffering of Iranians, Venezuelans, and Cubans is unmistakable, and their rulers have never been weaker.
In Iran, sanctions have crippled the economy and collapsed the currency. Israeli and U.S. strikes dismantled nuclear facilities. Proxies lie in ruins—Hamas decimated, Hezbollah broken, Assad fallen. Yet the regime responds to protest with massacre, galvanizing international outrage and internal opposition.
Venezuela's economic collapse is catastrophic: over 80% live in poverty, more than 50% in severe poverty. Families scavenge for food while children die from preventable diseases as hospitals lack basic medicine. The professional class has fled—doctors, engineers, teachers abandoning their homeland.
Cuba faces imminent collapse. Rolling blackouts plunge the island into darkness daily. Chronic shortages of basic goods and medicines plague the population. Subsidized Venezuelan oil kept Cuba's lights on since 1999—that lifeline is severed. GDP per capita has fallen 40% since 2019, 10% more than the U.S. during the Great Depression.
Securing the Guns
Thus, the first three criteria are clearly met in each of the three countries. The fourth criterion presents the greatest challenge.
Iran represents the hardest case: 190,000 IRGC troops plus 600,000 Basij militia, heavily armed and ideologically committed. No signs of mass defections. 47 years of oppression eliminated alternative power centers. Without military elements willing to accept democratic transition, intervention risks creating power vacuums.
Venezuela represents the strongest candidate. Trump's choice of Delcy Rodríguez—Maduro's vice president—signals he learned Iraq's lesson about purging power structures. Some insiders report Trump refused to back Machado because she didn’t control the guns, but Venezuela retains civil society and recent democratic traditions. Elements within security apparatus accepted transition.
Cuba falls between. Ricardo Zúñiga, who negotiated Obama's detente, says "there's nobody who would be tempted to work on the U.S. side." Over 70 years, the regime never negotiated regarding its political system. Yet Venezuela's oil cutoff threatens collapse, potentially forcing security forces to choose between a sinking ship or democratic transition.
The Path Forward
Despite Maduro's capture, Venezuela's regime remains in place. Iran has crushed its revolution—for now. Whether Trump will truly change these regimes remains unclear. What's even less clear is whether his administration will do what's needed.
"Nation-building" evokes post-Saddam chaos, but the fear is misplaced. What's needed is democratic institution building—supporting free elections, constitutional reforms, independent judiciaries, and civilian control of security forces. Vance's negotiations legitimize brutal regimes. Miller's realpolitik ignores transforming lives. Both miss what history proves: regime change without democratic institutions is doomed.
Both miss what history proves: regime change without democratic institutions is doomed.
Don't pursue resource gains or stability via autocrats. Cultivate military defectors within Iran's security apparatus. Restore Venezuela's democratically elected government and ensure Machado secures the guns. Help populations build institutions that prevent tyranny's return.
Anything less wastes American power and squanders the greatest opportunity for the liberation and prosperity of tens of millions in over a generation.
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