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Theodore Roosevelt: Today we are debating the ethics of regime change in Iran, and this is a three-part series. In Part One, which you are watching right now, we establish the fundamental question: does any nation ever have the right to topple another government, and does the United States have that right in the case of Iran? In Part Two we get specific, examining Iran’s actual record, the nuclear program, the proxy wars, the 1953 coup, and what the real-world consequences of intervention would look like. And in Part Three we arrive at the deepest question of all: who gets to decide? That is where things get truly heated, and I will leave it at that.
Woodrow Wilson: I will add that by Part Three, Theodore’s composure will have entirely abandoned him, which will be both predictable and illuminating. But for now, let us begin with first principles, because that is where honest disagreement must start, even when one of the parties at the table is constitutionally incapable of honest disagreement.
Theodore Roosevelt: And let me say, Woodrow, it is a genuine displeasure to be seated across from you today. I have debated better men and lost more sleep over weaker arguments than yours. So let us get right to it. The question before us is whether the United States of America has not only the right but in certain cases the absolute obligation to remove a hostile, destabilizing, and dangerous regime from power. And I mean Iran. And I mean yes. Emphatically, unapologetically, and without the hand-wringing that I know you are already preparing to unleash upon me.
Woodrow Wilson: Theodore, your enthusiasm for violence as diplomacy has never ceased to astonish me. You mistake aggression for strength and call it virtue. But I will be civil, because unlike some people at this table, I believe civilization actually requires civil behavior. The United States of America was founded on a principle, and that principle is the self-determination of peoples. Every nation has the right to choose its own form of government, however imperfect that government may be. That is not weakness. That is the bedrock of legitimate international order. And if you had spent less time on horseback and more time reading, you might have encountered that idea.
Theodore Roosevelt: Oh, I read plenty, Woodrow. I read history, which you seem constitutionally incapable of doing without filtering it through a fog of idealism so thick you cannot see the bodies it has produced. Self-determination! A lovely phrase. It rolls off the tongue magnificently. And what does it mean in practice? It means you watch a theocratic regime brutalize its own people, destabilize its neighbors, fund terrorism across three continents, and develop nuclear weapons, and you say: well, they determined that themselves, so who are we to object? That is not a foreign policy. That is a suicide note written in the name of principle.
Woodrow Wilson: And your alternative is what, exactly? You storm in with guns and flags, overthrow whatever government displeases you, install a friendlier face, and call it liberation? We tried that, Theodore. Your spiritual heirs tried that. In 1953, American intelligence services overthrew the democratically elected Prime Minister of Iran, Mohammad Mosaddegh, and installed the Shah. And what did seventy years of that logic produce? It produced the Islamic Revolution of 1979. It produced the very regime you now want to overthrow. The blowback from your brand of strategic intervention is the problem we are currently debating. Does that not give you even a moment of pause?
Theodore Roosevelt: It gives me a moment of clarity, actually. The lesson of 1953 is not that intervention fails. The lesson is that intervention, once undertaken, requires the full commitment of national will and long-term strategic vision, neither of which was applied. You do not plant a flag and walk away. My Roosevelt Corollary to the Monroe Doctrine was explicit: if a nation demonstrates that it cannot or will not maintain order and meet its international obligations, then a civilized power has not merely the right but the responsibility to intervene and restore stability. That principle does not expire because the geography shifts from Latin America to the Persian Gulf.
Woodrow Wilson: The Roosevelt Corollary. Yes. Let us talk about that. You essentially declared the entire Western Hemisphere an American protectorate and reserved the right to intervene whenever you decided another nation was insufficiently civilized. And who appointed the United States the arbiter of civilization? You did, Theodore. Unilaterally. With a very large stick. You will notice that the nations on the receiving end of that corollary did not generally consider themselves liberated. They considered themselves occupied.
Theodore Roosevelt: Oh, and your record is so clean? You sent troops into Mexico, Haiti, and the Dominican Republic, Woodrow. You occupied Haiti for nineteen years. Nineteen! While talking about self-determination! At least when I intervened, I did not wrap it in sanctimonious language about making the world safe for democracy and then do exactly the same things I condemned. You are a man who preaches water and drinks wine, and then delivers a fourteen-point sermon about the virtues of sobriety.
Woodrow Wilson: Those interventions were mistakes, and history has judged them as such. I will own that. But the existence of my failures does not validate your philosophy. Two wrongs do not produce a doctrine. And my Fourteen Points, whatever their imperfect application, at least articulated a vision of international order based on law, consent, and self-determination, rather than on who has the bigger navy. The League of Nations would have created a framework precisely to manage situations like Iran without requiring unilateral military action. But your party killed it. Your party killed the one institution that might have made your cowboy adventurism unnecessary.
Theodore Roosevelt: Now we are in agreement on one thing, Woodrow. The Senate rejection of the League was a catastrophe. But not for the reason you think. It was a catastrophe because it left America without a coherent framework for exercising the global leadership it had already earned and already needed to provide. It did not leave America with the luxury of non-intervention. That luxury never existed. The question was never whether America would shape the world. The question was whether it would do so with clear eyes and strategic purpose, or whether it would stumble through history pretending its choices had no consequences.
Woodrow Wilson: And now, at last, we are approaching something resembling substance. So let me do you the courtesy, Theodore, that I suspect you will not fully return: let me present your argument at its strongest before I address it. Because that is what honest debate requires, even if it pains me to do it with a man whose idea of careful deliberation is charging up a hill and shooting things.
Theodore Roosevelt: High praise from a man who screened Birth of a Nation in the White House and called it history. But please, proceed with your generous steelmanning. I am sure the experience of fairly representing someone else’s ideas will be instructive for you.
Woodrow Wilson: The strongest version of Theodore’s argument runs something like this. The Islamic Republic of Iran is a genuinely dangerous actor. It is not merely a government with different values from America’s. It is a destabilizing regional power that has exported terrorism, armed proxy forces across the Middle East, brutalized its own population with documented systematic human rights violations, suppressed women’s rights with violence, executed political dissidents, and is actively pursuing nuclear weapons capability that would fundamentally alter the balance of power in one of the world’s most volatile regions. Furthermore, the regime is not broadly popular, as demonstrated by repeated massive protest movements, including the 2009 Green Movement and the 2022 Woman Life Freedom uprising, both of which the regime suppressed with lethal force. Therefore, the argument goes, regime change in Iran would serve both American strategic interest and the genuine interests of the Iranian people, and a powerful nation capable of bringing it about has both the strategic rationale and perhaps even the moral obligation to act. That is the steelmanned version of Theodore’s position. I will grant it is not nothing.
Theodore Roosevelt: Gracious of you. I notice you delivered that summary with the enthusiasm of a man reading a tax document, but credit where it is due, you got the substance right.
Woodrow Wilson: I got it right because I am honest, which is more than I can say for the version of my argument you are about to produce. But go ahead. Show the audience what fair representation looks like when attempted by a man who once called critics of his foreign policy flapdoodle pacifists.
Theodore Roosevelt: I called them that because they were. But fine. The strongest version of Woodrow’s argument, and I will be generous because demolishing a weak argument is no sport at all, runs as follows. The principle of national sovereignty and self-determination is not merely an idealistic abstraction. It is the foundational rule of international order, and without it, there is no order, only the law of the jungle dressed up in diplomatic language. If the United States arrogates to itself the right to determine which governments are legitimate and which deserve to be overthrown, it establishes a precedent that any sufficiently powerful nation can apply against any other. Today America topples Iran. Tomorrow Russia invokes the same logic to justify Ukraine. China invokes it regarding Taiwan. The precedent destroys the very international framework that has prevented great power conflict since 1945. Furthermore, Woodrow would argue, the historical record of American-sponsored regime change is not a record of success. Iran 1953 produced the 1979 revolution. Iraq 2003 produced ISIS and a failed state that destabilized an entire region. Libya 2011 produced a decade of civil war. The unintended consequences of intervention consistently outweigh the intended benefits, and a nation that has been the target of external interference does not respond with gratitude. It responds with nationalism, radicalization, and intensified hostility. That is Woodrow’s argument at its most formidable. Now let me explain why it is still wrong.
Woodrow Wilson: Oh, I cannot wait for this.
Theodore Roosevelt: The argument from precedent is the weakest refuge of those who will not act. Yes, powerful nations will always seek justifications for their interests. The answer to that reality is not to tie American hands with a principle that applies to everyone equally regardless of actual threat level. The answer is to exercise power wisely, strategically, and with clear-eyed assessment of what is actually at stake. Iran is not a normal case. A theocratic regime that chants death to America as official state policy, that has murdered American soldiers through proxy forces in Iraq and elsewhere, that is weeks away from nuclear weapons breakout capacity, that funds Hamas and Hezbollah and the Houthis simultaneously, is not a regime that the principle of self-determination was designed to protect. Woodrow’s principle was designed to protect peoples from external domination. The Iranian people have been demonstrating for decades that they want to be protected from their own government. We would not be imposing our will on the Iranian people. We would be removing the boot from their necks.
Woodrow Wilson: And yet it would be our hands doing the removing, on our timeline, by our methods, producing a successor government of our choosing. That is not liberation, Theodore. That is a different kind of domination with better branding. And I notice that the Iranian people, despite their genuine and heroic resistance to this regime, have not asked for American military intervention. They have asked for support, for solidarity, for the lifting of sanctions that hurt ordinary citizens. They have not asked to be shocked and awed into a new government by the country that put the Shah on the throne in the first place. You cannot bomb your way to legitimacy, and you cannot install it either. It has to grow from within, or it does not grow at all.
Theodore Roosevelt: And while it grows from within, at its own organic pace, it builds a nuclear weapon. Wonderful. I am sure the principles will provide some comfort then.
Woodrow Wilson: And there it is. The nuclear argument. The ace you have been holding since the opening hand. We will get to that, Theodore. We will get to that properly, because it deserves more than a rhetorical flourish. But I will say this much now: the existence of a genuine security threat does not automatically justify any and all responses to that threat. The question is not only whether Iran is dangerous. The question is whether regime change, specifically, is the right response, whether it would achieve its stated goals, what it would cost, and whether the alternatives have been genuinely exhausted. Those are questions your philosophy tends to skip on the way to the cavalry charge.
Theodore Roosevelt: And your philosophy tends to answer them by forming a committee, drafting a resolution, and congratulating itself on its restraint while the situation deteriorates into something far more dangerous and far more expensive to address. We have been running that experiment in slow motion for forty-five years. The results are not encouraging.
Woodrow Wilson: This conversation is not over. Not by a long shot.
Theodore Roosevelt: On that, at least, we agree completely.
