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Today, I was happy to join my friend Marlon Weems of The Journeyman. We talked through the latest news and a lingering question on my mind.
Right before the stock market closed on Monday, Trump told a reporter that the Iran War would end “very soon.” No concrete timeline. No details. No change on the ground. Nothing. The rest of his own administration was simultaneously saying the opposite. And yet the second Trump’s words hit the wire, oil dropped, and stocks rose.
I’ve been asking the same question every time this happens: Who was on the other side of that trade? Because this isn’t the first time. It’s a pattern. A statement gets made, markets move, and somewhere someone likely bought the dip. I’m not the only one asking this question.
On CNN, former Trump National Security Adviser John Bolton said Trump “could be manipulating the markets” with the “very soon” comment, noting that if there’s anything this president is obsessed with, it’s markets and gas prices. The fact that a former adviser is willing to say it out loud on CNN tells you something about how naked this pattern has become.
It truly has become a pattern. We saw it around Liberation Day tariffs. We’ve seen suspicious Polymarket activity tied to the exact timing of Iran strikes. And as Marlon Weems and I discussed, the rise of unregulated prediction markets has made the problem exponentially worse. These platforms don’t just track political outcomes anymore. They’ve turned every press conference, every government action, every pre-recorded television appearance, reality itself into an insider trading opportunity.
That’s the spine of this conversation. But it goes further than markets. Marlon and I also got into the school strike in Iran that killed nearly 200 girls and teachers, likely executed by the U.S., and why the absence of universal outrage is a moral failure this country will have to reckon with.
We talked about how Democrats should be handling this, what the next president has to do with the power that’s been handed to them, and why the infrastructure gap in independent media is one of the most consequential and least discussed political problems of this moment. Marlon brings 30 years on Wall Street to this conversation. You won’t want to miss it.
You can watch the conversation in full above and read key takeaways below.
Who Bought The Dip Before Trump’s “Very Close” Iran Comments?
This is the question that must be answered.
I laid out the core sequence: Trump gave his “very soon” comment to a reporter right before the stock market closed on Monday. Oil, which had been trading between $100 and $120, dropped immediately. Stocks rose. There was no factual basis for the statement. No ceasefire, no negotiations, no change in military posture. The market moved on words alone, and I said directly that my question every time this happens is who knew the statement was coming and positioned accordingly before it hit.
Marlon pointed out that before the Iran strikes were publicly announced, a bet of roughly half a million dollars appeared on Polymarket tied to the exact timing of the operation. His read, and mine, is that this almost certainly wasn’t one person acting alone. It’s a pool of people with access to information that the public doesn’t have. That’s not speculation. That’s the only logical explanation for that kind of precision.
Marlon also raised the Liberation Day tariff situation as a parallel. When the full scope of Trump’s tariff announcement hit, markets dropped roughly 20%. There were reports of congressional members holding positions that would have benefited from exactly that outcome. This is not a new playbook. It’s the same playbook being run over and over again.
Marlon noted from his Wall Street background that this kind of insider advantage has always existed in financial markets. What prediction markets have done is take that dynamic and extend it to every public event, every government action, every press conference. People closest to power can now monetize that proximity in ways that are completely unregulated and largely invisible.
The School Strike That Should Have Ended Everything
This is the part of the conversation that has been eating at me, and I want to say it plainly.
175 girls and teachers were killed in a school strike that reporting strongly indicates was carried out by the United States military. The administration’s response has been to deny it, deflect, and move on. I said in this conversation that the war should have ended the day after that happened. Not wound down. Ended. Full stop.
I made a comparison that I think is worth sitting with. I grew up near Quantico in Virginia. If Iran struck a school near Quantico in a war launched with no coherent justification and meandering goals that changed by the day, and 160 American girls were killed, we would have invoked Article 5. It would have been bigger than Pearl Harbor. We would have been in World War III within hours. The fact that this atrocity has not produced universal outrage is a direct consequence of whose children were killed. They are brown children in a country we have been conditioned to dehumanize. That is the only explanation for the silence.
Marlon made the point that for the first time in his memory, America has entered a war without the public behind it, even at the outset. After 9/11, he didn’t vote for Bush, but he was in New York when the towers came down, and he was flying the flag. People came together. That has not happened here. Support for this war started low and will only go down. I said that the highest support for any war is always at the beginning. It doesn’t go up. And if this is the peak, the arc of public opinion is going to be brutal for this administration.
I raised the broader point about the JCPOA. Iran was complying with the nuclear deal by every objective measure, including Trump’s own State Department’s 2018 report and the UN’s atomic watchdog. Trump tore it up anyway. If you’re Iran and you watched that happen, the rational conclusion is that the only real deterrent is a nuclear weapon. North Korea isn’t getting bombed. Gaddafi gave up his weapons program and ended up dead. The lesson authoritarian regimes draw from American foreign policy is consistent, and Trump just reinforced it catastrophically.
Independent Media & The Infrastructure Gap
We closed on something that Marlon and I think about constantly.
Marlon made the observation that trust has migrated. People are walking away from CBS and other mainstream outlets and are actively choosing individual voices they trust over institutions they don’t. That’s a structural shift. And independent journalists who operate without corporate pressure, without sponsors who can pull ads, without bosses who need access to the White House, are positioned to fill that space in a way that legacy media structurally cannot.
I raised the infrastructure gap directly. Kamala Harris raised a billion dollars in grassroots donations, mostly in 2024. After the election, that money evaporated back into the void. I keep coming back to this: what would have happened if even a fraction of that went toward building independent media infrastructure? Not one outlet. Infrastructure. A system. The right has been doing this for decades. Every fringe right-wing voice on Substack gets subscriptions from a coordinated network.
I was honest about the financial pressure this creates. Right-wing organizations and sponsors hit my inbox regularly. Left-leaning ones almost never do. I said plainly that this is how people get bought. A Black creator starts getting equipment, gets offered money, starts softening their takes, and six months later, they’re saying things that would have been unrecognizable to their earlier audience. Candace Owens is the clearest example, but she is not the only one. The money is there on the right. It is largely absent on the left. And that asymmetry has real consequences for what voices get amplified and what arguments get made at scale.
I said what I believe: rising with your integrity intact is slower. It is harder. I could go on TV tomorrow, agree with conservatives, and I would be rewarded financially for it immediately. I’m not going to do that. But I want people who watch this and read this to understand that supporting independent voices financially is not just a nice gesture. It is the mechanism by which honest journalism survives in this environment. If you find someone whose work you trust, support it.
Bottom Line
Trump’s “very soon” comment moved markets. John Bolton, a former Trump adviser, raised the possibility on national television that the president could be manipulating markets deliberately. The pattern of suspicious trades around major administration announcements, from tariffs to Iran strikes, is too consistent to dismiss as a coincidence. The press needs to be asking these hard questions. Marlon and I definitely are.
This war has already killed innocent girls in a school strike. The administration denied it and moved on. The moral clarity required to oppose this should not be complicated.
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