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This was one of the best foreign policy conversations I’ve had on this platform. Adam Ali is one of the sharpest foreign policy minds I know, and it was great to really get into the weeds on exactly why President Trump and his administration of sycophants are failing in this war.
We dissected the truth about what has gone wrong, piece by piece.
We covered everything. The closed planning circle that excluded virtually the entire national security apparatus. The hubris that came from Venezuela and the 12-day war. The failure to build a coalition. The total misunderstanding of what motivates an ideological regime like Iran. The JCPOA and how Trump’s destruction of it made any future deal impossible. The consequences nobody planned for. And a closing conversation about the American project itself and whether we can still leave it in a better place than we found it.
Adam opened with something that set the tone for the whole conversation. He said watching a world order that our grandparents built being thrown out at a rapid clip keeps him up at night. It keeps me up, too. But we did not end in despair. We ended with something closer to resolve.
You can watch the full conversation above and read key takeaways below.
The Closed Sycophantic Planning Circle & The Hubris Behind It
One of the most consequential structural failures of this war was the decision to keep planning within an extremely small group. The Wall Street Journal’s reporting revealed that the interagency process, the weeks or months of deliberation, and the airing of dissenting views were all skipped. What you get when you skip that process is a war launched without anyone in the room who would tell the president what he did not want to hear.
Adam made the point directly from the WSJ reporting. Typically, war preparations include weeks or months of classified deliberations, written planning documents, dissenting views from diplomats and intelligence officials, and National Security Council meetings with cabinet members. None of that happened here. The narrowed circle narrowed the advice, the information, and the range of scenarios the president was forced to consider before committing American forces.
I raised the purge of the general officer ranks as the deeper structural explanation. There are no Mark Milleys, no Mark Espers in this Pentagon. The people who would have walked into the Oval Office and said this is a catastrophic idea have been systematically removed and replaced with loyalists. General Caine reportedly warned Trump directly that Iran would close the Strait of Hormuz in retaliation. Trump dismissed it. When you build a command structure of people who tell you what you want to hear, you get a war built on what you want to believe.
Adam traced the hubris directly to Venezuela. The Maduro operation went off without consequence, without pushback, without visible blowback. Trump got high off it. And critically, as Adam noted, Cuba is already in an energy crisis, a consequence that nobody in that small circle was thinking about. The pattern was set. Take the excursion. Declare success. Move on. Iran was supposed to be the same playbook.
The Coalition Failure & What It Reveals About Trump’s Worldview
Even if you accept every false premise of this war, the failure to build a coalition before launching it is indefensible. Europe was given minutes of notice. Gulf allies who were going to absorb Iranian retaliation were not warned. And now Trump is going back to those same allies, begging them to help protect the Strait of Hormuz, and getting nothing. Adam drew the Iraq comparison precisely because it shows how far below even that catastrophically flawed precedent this war falls.
Adam walked through the post-9/11 Camp David meeting where Bush’s war cabinet assembled within days of the attack. Even with Ground Zero still on fire, the Bush administration spent months building political consensus, assembling a coalition, and prepositioning assets from spring 2002 through the March 2003 launch. Fifty countries had signed on fifteen days after the war began. That war was launched dishonestly, and the outcome was catastrophic. But the work was done. Here, our Gulf allies learned about the strikes from the news.
Adam noted that the Gulf states are furious and for reasons that go beyond politics. Saudi Arabia, the UAE, Dubai, Qatar, Oman, and Jordan have spent decades trying to position the region as a stable, tourist-friendly, economically open zone. Dubai is now under fire almost daily. Oman, which was facilitating negotiations, is under attack. These are countries that had every reason to believe Trump was their ally. He took billions in investments, hosted state visits, and collected diplomatic wins. And then he launched a war that immediately destabilized everything they had spent decades building without a single heads up.
I made the point that has not gotten enough attention. Trump spent his entire first year of this term attacking NATO allies, threatening Greenland, calling European leaders freeloaders, and undermining every relationship he could. And then he turned around and asked those same allies to send their ships into a minefield in the Strait of Hormuz to clean up a mess he created without consulting them. The fact that they are refusing is not a betrayal. It is a completely rational response to how they have been treated.
What Trump Fundamentally Misunderstands About Iran
This is the section of the conversation that gets to the root of everything. Trump did not just miscalculate tactically. He went into this war with a fundamental misunderstanding of what Iran is, what motivates the regime, and why no deal was ever going to emerge from decapitating its leadership. Adam put it plainly: Trump does not understand ideologues. He does not understand people with sincerely held beliefs. He thought he would find his Delcy Rodriguez.
Adam laid out the core delusion. Trump genuinely believed that if you remove enough layers of Iranian leadership, someone would raise their hand and say they wanted to make a deal. He projected his transactional worldview onto a regime that is ideological to its core. He thought Iran was Venezuela. Iran is not Venezuela. The Iranian regime has survived 47 years of isolation, sanctions, the Iran-Iraq war, and repeated military degradation precisely because survival is what it considers victory. The regime still stands. By their own logic, they are winning.
I raised the 1953 coup because it is the historical context that makes everything else legible. The US and UK overthrew Iran’s democratically elected government to secure oil interests. Iran has never forgotten it. Everything that followed, the 1979 revolution, the IRGC, the hostility toward any deal with Washington, flows from that original betrayal. Trump does not know this history. Witkoff made comments about uranium enrichment technology during the Geneva negotiations that were, as I said on the Live, just insane. These were not serious negotiations. They were theater.
Adam made the point about Marco Rubio that I think is one of the sharpest analytical observations in the whole conversation. Rubio cut his teeth in Bush world. Trump has railed against neoconservative ideology since he came down the escalator. But he has been morphed into the instrument of the very ideology he claimed to hate, out of desperation, out of vanity, out of his need to exert power somewhere when his domestic position was weakening. He has become what he said he hated and does not appear to know it. Or he does know, and just doesn’t care.
The Tearing Up Of JCPOA & The Destruction Of American Credibility
Nothing in this conversation made me angrier than the section on the JCPOA. Because the people who are now claiming Iran was never going to comply with any deal are the same people who destroyed the one deal that was working. Trump’s own State Department said Iran was in compliance. The UN’s atomic watchdog said Iran was in compliance. Every objective observer said Iran was in compliance. And Trump tore it up anyway because of his hatred of Obama.
Adam made the credibility argument in terms that go beyond Iran. We have now established a pattern that the words of a Republican president mean nothing. And the words of a Democratic president mean nothing either, because a Republican can come in and declare the previous administration illegitimate and tear up whatever agreements were made. No country can negotiate with that. The destruction of the JCPOA did not just end one deal. It ended America’s ability to be a credible negotiating partner for the foreseeable future.
I raised the North Korea comparison because it illustrates the lesson every regime is now drawing. Kim Jong-un has a nuclear weapon. Trump treated him with deference, flew to North Korea, gave him legitimacy, and never struck. Iran gave up its nuclear program under the JCPOA. Iran is now being bombed. Gaddafi gave up his nuclear program. Gaddafi was killed in the street. Ukraine gave up its nuclear weapons under the Budapest Memorandum. Ukraine was invaded. The lesson every authoritarian regime on earth is internalizing right now is that nuclear weapons are the only real protection against military force.
Adam added the USAID point as the soft power corollary. The alternative to war is soft power. It is USAID. It is the tools that build relationships, credibility, and influence without firing a single missile. This administration has shuttered those tools. And now reports are emerging of using AIDS funding in Africa as leverage. As Adam put it, this is how you end what historians will likely label the Pax Americana, the period between 1945 and roughly 2013 during which American power, for all its contradictions, maintained a certain global order.
The Ramifications Nobody Planned For
Adam’s framework from the beginning of the conversation was about the failure to consider second, third, and Nth order effects. We saw it in Venezuela, where Cuba is now in an energy crisis. We are seeing it in the Strait of Hormuz, where a closure the Trump Administration didn’t adequately plan for is threatening to destabilize the global economy. And we are going to keep seeing it as the downstream consequences of this war ripple out in ways the small planning circle never modeled.
Adam described what the endgame actually looks like from a clear-eyed view. The Washington Post reported this week that the Iranian regime is consolidating rather than collapsing. The more moderate elements that could have credibly negotiated an off-ramp are being killed off. Adam specifically named Larijani, a pragmatist by Iranian standards, as someone who might have been interested in a negotiated exit and who Israel says it killed this week. Every moderate voice removed is replaced by a more hardline one. We are not producing a compliant successor regime. We are producing a more radical one with a deeper personal grievance.
I raised the radicalization pipeline because it is the consequence that gets the least coverage. The school strike killed 165 children in Minab, a small town where everyone knew those girls. There are now young men in that region with a concrete, personal grievance against the United States and nothing to lose. We saw this in Iraq. We saw it in Syria. We are going to see it here. Iran’s proxies across the region are now more infuriated, not less. Syria was just starting to get its footing after years of destruction. Lebanon is being destabilized again. The conditions that produced ISIS are being recreated with a fresher grievance and a broader geographic footprint.
Adam closed this section with a quote from the Bush era that landed perfectly. Ron Suskind captured a Bush aide mocking the “reality-based community,” saying we are an empire now, we create our own reality. That arrogance was proven catastrophically wrong in Iraq. The same arrogance is operating here. And as Adam said, we have still not recovered from Iraq. We are still within that window of destabilization. What we have done now is pour gasoline back on it.
Bottom Line
Trump did not just miscalculate tactically. He went into this war without understanding the history, without understanding the ideology, without building a coalition, without a plan for the day after, without listening to the people who warned him, and without any apparent awareness that the enemy gets a vote.
Adam ended by quoting Ta-Nehisi Coates in a recent appearance with Ezra Klein. The struggle gets left where you leave it. Hopefully, in a better place. Oftentimes not. Our ancestors, our grandparents, the people who built the institutions and agreements that kept the world from tearing itself apart for seventy years, they did not live to see all of it pay off. Neither will we. But we leave what we leave, and the next generation picks it up.
America’s promise is real. The people who believe in it most are often the ones it has treated worst. That has always been true, and it remains true now. This is not who we are. And it is on us, right now, to prove it.
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