While in Wisconsin, President Donald Trump sat down with NBC News to discuss the ongoing U.S.-Iran military conflict. During the interview it was clear that Trump is fundamentally misreading the situation inside Iran.
When asked about negotiations with the Iranian government, Trump has said repeatedly that Mojtaba Khamenei and the new Iranian government are more rational, more open to negotiation, and less radical than the previous regime, and that Khamenei is deeply respected and admired by those serving beneath him in Iran’s military apparatus. Trump kept hammering home how revered the new leadership is within that apparatus.
But that only raised another question. If the military apparatus is so entrenched and self-sufficient that its respect for Mojtaba needs to be established as a selling point, that same apparatus could just as easily stymie any leader it deemed too conciliatory toward the United States. The authority of a supreme leader should not need to be argued. The fact that Trump feels compelled to argue it raises the question of whether any deal reached through Mojtaba would hold at all, and whether there is truly a self-sustaining, hardline military dictatorship in Iran that does not need a supreme leader.
Throughout the interview, Trump pointed to Venezuela as a benchmark for what success looks like, describing it as a “total takeover” without a single American casualty, yielding a new government with strong U.S. relations. Suggesting that Delcy Rodriguez represents a meaningful break from Maduro is a considerable stretch: she served as his foreign minister and vice president for years and has faced U.S. sanctions herself. The notion that the United States, or anyone, could engineer a clean transition producing lasting cooperation through one overnight military action is far-fetched.
Trump may well be satisfied with a simpler formula: extend public warmth toward an adversarial, lesser-of-two-evils figure, extract enough visible wins to claim progress, and keep that leader on a short leash. That appears to be exactly what he has done with Rodriguez, and it may be what he has in mind for Iran, with little apparent regard for the actual fitness of the candidate.
According to a recent New York Times report , the United States and Israel entered the conflict with Mahmoud Ahmadinejad as their preferred successor, a former Iranian president best known for denying the Holocaust, calling for Israel to be wiped off the map, and accelerating uranium enrichment. An associate of Ahmadinejad told the Times that Washington viewed him as playing a role similar to Delcy Rodriguez, which only deepens the concern that this administration has a shallow grasp of Iranian politics and history.
Struggling to close any meaningful deal with Iran, Trump may ultimately settle for something comparable to the Obama-era nuclear deal, rebranded with his name on it but offering little substantive progress over the original agreement. That would probably be enough for him to call it a win. Even getting to this resolution of the current conflict, however, faces two problems.
First, the Iranian government is unlikely to rush into a favorable deal. Iran is a country that has carefully cultivated a long memory of Western interference, deploying that victimhood narrative as the vehicle by which the regime conceals its internal repression and cloaks authoritarian control in the language of resistance to imperialism.
Ayatollah Ali Khamenei, killed in U.S. and Israeli strikes, was the embodiment of that accumulated grievance and the anti-Western struggle the regime uses as its central justification. Without enormous and sustained pressure, Trump’s flattering of his successor is unlikely to overcome this legacy of anti-imperialism.
Second, dealmaking with dictatorships is extraordinarily difficult and slow. Negotiations between the P5+1 and Iran began in earnest around 2003, went through multiple rounds that collapsed, and did not produce a framework agreement until 2015. Neither side trusts the other, so enormous time is spent designing inspection mechanisms, compliance triggers, and snapback provisions that both sides can live with.
The reason Trump makes both Venezuela and Iran sound like quick and easy victories is because it reflects his intent to present every military engagement as a fast, clean win in the style of a Manhattan real estate deal, and to make himself and the Republican Party appear decisive and strong. But the spread of democratic governance is not a quick fix and does not carry with it the traits of corporate dealmaking. Trump himself acknowledged as much in the same NBC interview, referencing the length of the Vietnam War.
The situation is genuinely strange. A sitting U.S. president offering to meet directly with an Iranian leader is remarkable given that American policy toward Iran has long been built around indirect talks and deliberate distance, premised on a baseline of mutual distrust so deep the two governments will not speak face to face. Direct engagement is only worth the risk if the administration pairs it with concrete, public demands: a halt to uranium enrichment, the release of political prisoners, and meaningful strides toward providing the Iranian people freedom.
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